أساسيات الكيمياء العضوية by mohib.h

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									                                                  ‫א‬‫א‬‫א‬
                                               ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                                   ‫א‬‫א‬‫א‬‫א‬




‫א‬
               ‫א‬‫א‬

                               ١٤٠
        ‫א‬                                   ١٤٠                                    ‫א‬
                                          ‫א‬‫א‬                     ‫א‬



          W،،‫א‬‫א‬،‫א‬
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  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
    ‫א‬ ‫א‬  ،‫א‬   ‫א‬ ‫א‬ ‫א‬ ‫א‬ ‫א‬ 
  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
  W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                   
                                                                K‫א‬‫א‬‫א‬
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  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
    ‫א‬        ،‫א‬ ‫א‬‫א‬  
  ‫א‬  ‫א‬ ‫א‬ ‫א‬ ‫א‬ ‫א‬   ‫א‬    ،  
  ‫א‬،‫א‬‫א‬‫א‬‫א‬
  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
       ‫א‬  ‫א‬   ،‫א‬   
                                       K‫א‬‫א‬،‫א‬‫א‬
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  ‫א‬  ?  ? ‫א‬ ‫א‬  ? ‫א‬ ‫א‬  
   K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬?
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  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
  ،‫א‬،‫א‬‫א‬‫א‬‫א‬
                             K‫א‬‫א‬‫א‬‫א‬‫א‬
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     W    ‫א‬ ‫א‬  ‫א‬    ‫א‬
                                                                                                 K‫א‬
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 ‫א‬‫א‬‫א‬‫א‬                                            
                                                ١٤٠                                       ‫א‬
                                             ‫א‬‫א‬                        ‫א‬



‫א‬،KK‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                          
،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬،‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
–‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬–‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،،‫א‬
                                                                                          
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ 
‫א‬،‫א‬‫א‬‫א‬‫א‬K
‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                                                                        K‫א‬
                                                                                
‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬،‫א‬‫א‬
                 K‫א‬‫א‬‫א‬‫א‬،‫א‬
                                     ‫א‬‫א‬‫א‬
                                  ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                      ‫א‬‫א‬‫א‬‫א‬




             ‫א‬‫א‬
                    
 




١
    ‫א‬‫א‬                              ١٤٠                                     ‫א‬
                              ‫א‬‫א‬                      ‫א‬



                                                                                                W‫א‬‫א‬
،‫א‬‫א‬،‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
                                                                               K‫א‬‫א‬‫א‬


                                                                                     W‫א‬‫א‬
                                                 W‫א‬‫א‬‫א‬
                           K‫א‬‫א‬‫א‬‫א‬‫א‬                -١
            K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬             -٢


                                                                              W‫א‬‫א‬‫א‬
                                                   K٪٨٠‫א‬‫א‬‫א‬


                                                                                  W‫א‬‫א‬
                                                                                         K‫א‬


                                                                                W‫א‬‫א‬
                                                       KOverhead Projector
                                                                    K‫א‬‫א‬


                                                                                     W‫א‬‫א‬
                                                                      K‫א‬‫א‬‫א‬‫א‬




                                                  -١-
     ‫א‬‫א‬                                  ١٤٠                                     ‫א‬
                                   ‫א‬‫א‬                      ‫א‬



                                                                                              W١J ١
K‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬Organic
  
،،‫א‬‫א‬،‫א‬
‫א‬،‫א‬،‫א‬‫א‬‫א‬K‫א‬
                
‫א‬1828 Wohler‫א‬‫א‬‫א‬‫א‬K‫א‬
‫א‬‫א‬E‫א‬F‫א‬
                                                                                    W‫א‬‫א‬،
                                                                                                           
                                                                         O

                             NH4OCN                        H2N          C   NH2
                                                      
                                                
‫א‬‫א‬‫א‬،‫א‬،‫א‬
                                                                 K‫א‬،
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬ K‫א‬‫א‬‫א‬
                 
‫א‬‫א‬‫א‬‫א‬K
                                       K‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬
                                                                   
،‫א‬‫א‬‫א‬‫א‬ K‫א‬
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                        K‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                   K‫א‬


                                                          -٢-
    ‫א‬‫א‬                                     ١٤٠                                       ‫א‬
                                     ‫א‬‫א‬                       ‫א‬



‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬KFunctional Groups  ‫א‬‫א‬
                                                                               
                                     
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
E–OHF‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬K
        
‫א‬‫א‬Ksp3‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                  K‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                                                                                 

                                                      WFunctional Group ‫א‬‫א‬١J ٢
‫א‬‫א‬‫א‬‫א‬‫א‬ 
                                                                              
،،‫א‬‫א‬K‫א‬‫א‬‫א‬
                                                                                                            O

‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬                          C        H

                        W‫א‬‫א‬‫א‬‫א‬
                                                                                                                 
                                                             O
                                         [O]
                            O                        CH3C-OH                   ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
                       CH3C H
                                          [H]
                                                     CH3CH 2OH                   ( ‫) ﻏﻮل‬
                           ‫أ‬                                                                           
                                                        
                                          [O]
                            O                         CH3CH2COOH            ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
                   CH3 CH2C H
                                           [H]
                                                      CH3CH2CH2OH ( ‫) آﺤﻮل‬
                          ‫ب‬
                                                        




                                                            -٣-
     ‫א‬‫א‬                                    ١٤٠                                        ‫א‬
                                     ‫א‬‫א‬                         ‫א‬


                                           [O]
                                 O                     CH3CH2CH2COOH ( ‫) ﺣﻤﺾ آﺮﺑﻮآﺴﻴﻠﻲ‬
                 CH3CH2CH2C H
                                            [H]
                                                      CH3CH2CH2CH2OH ( ‫) آﺤﻮل‬
                                 ‫ج‬
                                                                                                         
                                                                                                                  
                                                                   
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫- ( א‬CHO)‫א‬‫א‬‫א‬
                                         
 ،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
                                                                                    
 ‫א‬‫א‬K‫א‬‫א‬‫א‬
 ،‫א‬‫א‬
                              
K‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                            K‫א‬‫א‬E١J ١F

                                      ‫א‬‫א‬WE١J ١F

                                                       ‫א‬                     ‫א‬‫א‬
                        
                                               ‫א‬‫א‬                 ‫א‬

                                                   ‫א‬
                   H2C      CH2                                                           C= C
                                                                               
                                             ‫א‬‫א‬
                                            E‫א‬‫א‬F
                                                                                      
                                                   ‫א‬                              C C
                  H C C             H                                         
                                                                                            X
                                     Br
                                              ‫א‬‫א‬‫א‬                             C
                 CH3I ,
         
                                                                             ( X = I, Br, Cl , F )
                                                   ‫א‬
                  CH3CH 2OH                                                               C OH
                                                                                   


                                                            -٤-
    ‫א‬‫א‬                                 ١٤٠                                                       ‫א‬
                                 ‫א‬‫א‬                                       ‫א‬



                                                ‫א‬‫א‬                                           O       C
          CH3 O           CH3                                                             C
                                                                       
                      O                                                                            O
                                              ‫א‬‫א‬
            CH3 C H                                                                              C H
                      O                                                                            O
                                              ‫א‬
                                                                                           C       C C
            CH3 C CH3                                                 
                 O                                                                             O
                                        ‫א‬‫א‬
              H C OH                                                                         C OH
                                            ‫א‬                                      O
                     O
                                           ‫א‬                         C Y
           CH3 C OCH 3                                                ( Y = Cl ,OR, NR 2 ,...)
                             CH3
                                                ‫א‬                                       C N
          CH3NH2 , CH3NH                                                      
                                               ‫א‬
                  CH3CN                                                                       C       C     N
                                                                           
                                NO 2                                                               O
        CH 3NO 2 ,                          
                                                                                           C N O-
                                                                           
                                                ‫א‬                                       C SH
                  CH3SH
                                                                                   


                                                                              W‫א‬‫א‬‫א‬١J ٣
K‫א‬‫א‬EF‫א‬‫א‬‫א‬‫א‬   
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬?hemolytic?‫א‬K‫א‬
            
K‫א‬‫א‬‫א‬?heterolytic?،
    K X‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                                            



                                                     -٥-
    ‫א‬‫א‬                                     ١٤٠                                      ‫א‬
                                    ‫א‬‫א‬                       ‫א‬



                                                         .
                       C . .X                       C. + X                " ‫" أﻧﻔﺼﺎم ﻣﺘﺠﺎﻧﺲ‬

                                               ‫ﺟﺬر ﺣﺮ‬
                                                       
                                                       
                                                            _




                                                                 }
                  C . .X                    C + + .X
                                                  .

                                      ‫أﻳﻮن آﺮﺑﻮﻧﻴﻮم‬
                                      carbonium ion
                                                                          " ‫" اﻧﻔﺼﺎم ﻏﻴﺮ ﻣﺘﺠﺎﻧﺲ‬

                                                _
                  C . .X                      .
                                             C. + X+

                                       ‫أﻳﻮن آﺮﺑﺎﻧﻴﻮن‬
                                      carbanion
                                                       
      
‫א‬K،‫א‬‫א‬‫א‬
                                                                             
‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
           K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
X‫א‬،‫א‬‫א‬‫א‬‫א‬
                                                                                  
K‫א‬،‫א‬ 
                                       
‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬X‫א‬E‫א‬F‫א‬‫א‬
KX‫א‬‫א‬‫א‬‫א‬E‫א‬F‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬‫א‬
                                                           
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                          
‫א‬،E‫א‬F‫א‬
K‫א‬‫א‬NucleophilesENu-F‫א‬ElectrophilesEE+F
                                                                                     
F‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬ ‫א‬
                            WK‫א‬E‫א‬

                                                           -٦-
    ‫א‬‫א‬                                       ١٤٠                                                            ‫א‬
                                      ‫א‬‫א‬                                            ‫א‬



                                      H+ , Br+ , NO2+ , BF3 , AlCl3
                                                                                                                                           
                                                                         
F‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                            WKE
                                                                                                                                           
                               . ._
                                  .    . ._
                                          .    . ._.    . ._
                                                           .     . ..     .
                              HO. . , RO. . , RS . . , CN . , H2O . , R2N .
                               .       .       .
                            
                                                                                                                                            
                                                                                                                                                 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                             W،‫א‬
                   ‫א‬،substitution‫א‬‫א‬‫א‬ J ١
                                                                   K‫א‬


                  CH 3CH2OH + HBr                                             CH3CH2Br +H2O
                                                   E‫א‬‫א‬F


                   ‫א‬‫א‬‫א‬Waddition‫א‬ J ٢
                                                 
                                                K‫א‬‫א‬‫א‬‫א‬‫א‬

                         CH2       CH2 + Br2                                       CH2BrCH 2Br
                                                             EF


                   ‫א‬،eliminationE‫א‬F‫א‬‫א‬ J ٣
                                                                 
                   ‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬
                                                                                                                               KE
                                                                                                                         
                CH3CH2Br + NaOH                                    CH 2 CH2 + H2O + NaBr
                                             E‫א‬‫א‬F

                                                                                                                                           
                                                            -٧-
 ‫א‬‫א‬                                      ١٤٠                                          ‫א‬
                                   ‫א‬‫א‬                          ‫א‬



                                                   
                                                  W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬W١
                                                                                                                 
                CH2OH
                                                              _
                                                                   ‫ب‬                  O
                            ‫- ح‬                     O
                                                                                CH 3C N(CH 3)2        ‫أ‬
       
                                                                                          CH3
                            _                                 _                     CH3 Pb      CH3      ‫د‬
      CH3CH 2F                 ‫و‬                                 ‫هـ‬
                                                                                         CH3
                                                                                
                                                                                                O
                                                    
                                                                                CH 3OCH 2CH 2C H             ‫ج‬
                                                                                                                 
                                                                                                                 
                          ‫؟‬‫א‬،‫א‬‫א‬‫א‬W٢
                                                                                                                     

                                       +                  -                 -
                               CH3CH2 , ZnCl2 , F , CH3CH2 , CH3OH , CH3SH , CH3NH2

                                                                                                                 
                                                                            W‫א‬‫א‬W٣
                     O
     a) - CH3 C H + CH3MgI                                    CH3CHCH3
                                                                       OMgI

     b) - CH3CH2I +                 NaSH                                 CH3CH2SH + NaI
     c) - CH2 CH CH3 + HCl                                    CH3CHCH 3
                                                                       Cl




                                                         -٨-
 ‫א‬‫א‬                         ١٤٠                                      ‫א‬
                      ‫א‬‫א‬                       ‫א‬



                             ١J ٤‫א‬‫א‬
                                                                                            W١
                  J J J J ‫א‬
                                                                                                 
                                                                                             W٢
                 K‫א‬‫א‬WCH3NH2
                 K‫א‬WCH3OH
                                                 KWF-
                                                 KW              ZnCl2

                                                                                                 
                                                       K‫א‬‫א‬‫א‬‫א‬W٣
                                                      K‫א‬‫א‬
                                                                                                 




                                          -٩-
                                                  ‫א‬‫א‬‫א‬
                                               ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                                   ‫א‬‫א‬‫א‬‫א‬




                          ‫א‬‫א‬
                          ‫א‬‫א‬
 ‫א‬‫א‬




٢
    ‫א‬‫א‬                                 ١٤٠                                      ‫א‬
 ‫א‬‫א‬                       ‫א‬‫א‬                       ‫א‬



                                                                                            W‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                   K‫א‬‫א‬‫א‬‫א‬‫א‬


                                                                                         W‫א‬‫א‬
                                                   J W‫א‬‫א‬‫א‬
                                                      K‫א‬‫א‬ .١
                                     K‫א‬‫א‬‫א‬ .٢
،E،،F‫א‬‫א‬‫א‬ ‫٣. א‬
                                                                          K‫א‬‫א‬


                                                                                    W‫א‬‫א‬‫א‬
                                                         K٪٨٥‫א‬‫א‬‫א‬


                                                                                        W‫א‬‫א‬
                                                                                                 K٨


                                                                                  W‫א‬‫א‬
                                                    KOverhead Projector .١
                                                                K‫א‬‫א‬ .٢
                                                                 K‫א‬‫א‬‫א‬‫א‬‫א‬ .٣
                                                                                            K .٤


                                                                                          W‫א‬‫א‬
                                                                           K‫א‬‫א‬‫א‬‫א‬



                                                       - ١٠ -
    ‫א‬‫א‬                              ١٤٠                                  ‫א‬
  ‫א‬‫א‬                   ‫א‬‫א‬                   ‫א‬



                                                                                          ‫א‬٢J ١
 
‫א‬‫א‬
                                                                                  W


                                                              W‫א‬J 
‫א‬‫א‬‫א‬
‫א‬K‫א‬‫א‬–‫א‬‫א‬،
                                                                                                    W
–‫א‬،saturated‫א‬‫ א‬K
                                
                                              Ethane CH3-CH3alkanes‫א‬
،J ‫א‬،unsaturated‫ א‬K
                                                                                      W
،EC=CF–‫א‬‫א‬،alkenes‫ א‬J ١
،EC C F–‫א‬‫א‬alkynes‫א‬
                                                                                    
                                                           
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                                                   K
،‫א‬Aromatic Hydrocarbons‫א‬‫א‬‫ א‬J ٢
                            K C10H8‫א‬‫א‬‫א‬


                                                                          WAlkanes‫א‬٢J ٢
،‫א‬‫א‬‫א‬،‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬




                                                    - ١١ -
   ‫א‬‫א‬                                     ١٤٠                                         ‫א‬
 ‫א‬‫א‬                          ‫א‬‫א‬                          ‫א‬




                                                                                             ‫א‬‫א‬‫א‬
nCnH2n+2W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬                       
‫א‬‫א‬K‫א‬‫א‬EnFEKKKKKKK،٤{٣{٢{١=nF
                                                                       
‫א‬،‫א‬،‫א‬
                                                                              K‫א‬


                                                                                     W‫א‬٢J ٢J ١
‫א‬‫א‬‫א‬،E-aneF‫א‬‫א‬
                                                                                                                          
E-aneF‫א‬‫א‬E‫א‬F‫א‬‫א‬
                                                                                        
                                                                              E١J ٢F،

                                         ‫א‬E١J ٢F

                n        ‫א‬‫א‬ ‫א‬
        1            methane                                       CH4
       2            ethane                                                 CH3CH3 
        3            propane                                                CH3CH2CH3            
        4            butane                                            CH3CH2CH2CH3
       5 pentane                                         CH3(CH2)3CH3
        6            hexane                                                  CH3(CH2)4CH3
        7            heptane                                                 CH3(CH2)5CH3
        8            octane                                                 CH3(CH2)6CH3             
        9            nonane                                                  CH3(CH2)7CH3
        10           decane                                                  CH3(CH2)8CH3 
                                                                                                                     



                                                          - ١٢ -
   ‫א‬‫א‬                                ١٤٠                                        ‫א‬
 ‫א‬‫א‬                     ‫א‬‫א‬                         ‫א‬



CH2‫א‬‫א‬‫א‬‫א‬
                  
‫א‬‫א‬،Methylene‫א‬
                                                                               W‫א‬‫א‬
                                                                                                               
                                                                                                               
                                                                                Butane C4H8W‫א‬‫א‬
                                                                              CH3 CH CH3
                          CH3-CH2-CH2-CH3
                          n-Butane                                    CH3
                                                                          IsobutaneJ 


                                                                         Pentane C5H12         W‫א‬‫א‬
                                                              
                                                                                               CH 3
                     CH3 CH CH2 CH3            CH3CH2CH2CH2CH3
                                                                                       CH 3     C      CH3
                                                              
                           CH3                                
                                                                                               CH 3
                                                                                        J 
                          –              –                      Neopentane
                           Isopentane                     N-pentane


                                                          WAlkyl Group ER-F‫א‬
‫א‬‫א‬ER-F‫א‬
                   
‫א‬‫א‬،methylCH3-‫א‬
‫א‬‫א‬‫א‬‫א‬E 2-2F‫א‬KEthylECH3CH2-F‫א‬
                                                                                        ‫א‬‫א‬




                                                     - ١٣ -
  ‫א‬‫א‬                                         ١٤٠                                  ‫א‬
‫א‬‫א‬                              ‫א‬‫א‬                   ‫א‬


                                                                                                                   


                         K‫א‬‫א‬١٠J ٢‫א‬

                                                  ‫א‬‫א‬
        ‫א‬‫א‬                                                              ‫א‬
                                                         ‫א‬
                Methyl                                 CH3J                     MethaneCH4
                     Ethyl                              CH3CH2-                   Ethane CH3CH3
                                                                                       Propane
                    N-Propyl                         CH3CH2CH2-
                                                                                     CH3CH2CH3
                                                          
                      Isopropyl                  CH3-CH-CH3                  CH3CH2CH2CH3
                       n-Butyl                      CH3CH2CH2CH2-
                     sec- Butyl                    CH3CHCH2CH3                       n-Butane        

                                                              CH3
                 Isobutyl                                       _
                                                  CH 3 CH CH 2
                                                                                         CH3
                                                                                  CH3 CH CH3
                                                                                      
                Tert-butyl                                          CH3             Isobutane
                                                     CH3 C                               
                                                                CH3
                                                              


                                                     Cycloalkanes ‫א‬‫א‬
    W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                   CH 2

                                                                             CH 2      CH 2
                                                                              Cyclopropane
                      
                                                                                                         
                                                             
                                                             - ١٤ -
   ‫א‬‫א‬                                    ١٤٠                                       ‫א‬
 ‫א‬‫א‬                         ‫א‬‫א‬                        ‫א‬



                                                                              CH2      CH2

                                                                            CH 2 CH2
                                               
                                                                             Cyclobutane
                                                                                    
                                                                CH2
                                                                             CH2          CH2
                                                                             CH2          CH2
                                                                       
                                                                             Cyclopentane
                           
                                                                                   
                                                                                              CH2CH3
                                                                                                      
                                                                     Ethylcyclopropane

                                                             WIUPAC‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
                                             IUPAC W‫א‬‫א‬،‫א‬‫א‬
International Union of Pure and Applied Chemistry.


                                                                                              W‫א‬‫א‬
                                                                          
E‫א‬F‫א‬‫א‬‫א‬‫א‬                            E١
                                   K‫א‬‫א‬‫א‬‫א‬
                          
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬                     E٢
                                       
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
                                                
،‫א‬‫א‬‫א‬‫א‬E‫א‬F‫א‬‫א‬EJ F
                   
‫א‬‫א‬‫א‬ane‫א‬
                                            W‫א‬‫א‬yl
                                                                                              
                                                           - ١٥ -
   ‫א‬‫א‬                                                ١٤٠                                                         ‫א‬
 ‫א‬‫א‬                                  ‫א‬‫א‬                                             ‫א‬


                                                   1         2    3        4        5       6
                                                  CH 3CH 2 CHCH 2CH 2 CH 3

                                                                CH 2CH 3
                                                                                                                        
                                     3-Ethylhexane
                            
E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬                                                     
‫א‬penta ،tetra،tri،di‫א‬،‫א‬‫א‬‫א‬
                                                                         
‫א‬‫א‬ KKKKKK،،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،
                                               W‫א‬‫א‬‫א‬
                                                                                                                                                 
                                                                                CH3
                                              CH3 CH CH2 C CH
                                              5              43        3            2           1
                                                            CH3                CH3
                                                                                                                                                 
                                                   2-2-4-Trimethylpentane
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬                                                
                                                                                                             W‫א‬‫א‬
                                                                                                                 
                                                                                            CH2CH3
                                  8           7          6         5            4           3           2       1
                                 CH3 CH2 CH2 CH CH C CH2 CH3
                                                   _
                                         CH3 CH2 CH2 CH3 CH2CH3
                                                                                                                                                 
                                                 3,3-Diethyl-4-methyl-5-n-propyloctane
                                                                                                                                                  
                                                             
‫א‬‫א‬‫א‬                                                           
                      W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                                                                 
                                 7            6              5         4                3           2          1
                                 CH 3 CH 2 CH CH 2 CH                                           CH 2 CH 3
                                                       CH 3                   CH 2CH 3
                                                                   - ١٦ -
    ‫א‬‫א‬                                  ١٤٠                                        ‫א‬
 ‫א‬‫א‬                      ‫א‬‫א‬                           ‫א‬



                                                        
                                                        3-Ethyl-5-Methylheptane
                                                                                                                  
                       
‫א‬‫א‬E‫א‬F‫א‬‫א‬            
،EaneF‫א‬EylF‫א‬،‫א‬
                 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                     
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                              W‫א‬
                                                    CH3 CH3
                                               1'           2'     _
                                          3  CH CH CH3
                              CH3 CH2     CH CH CH2 CH2 CH2 CH3
                              1    2                4       5          6   7        8
                                          CH2                    CH2CH3
                                         CH3
                                                                                                                  
                                        3-Ethyl-4(1',2',Dimethylpropyl) nonane
                                                                                                                  
                                     
E‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                           
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
                                                                                         W‫א‬E‫א‬

                      F: Fluoro                                            NO2W Nitro

              ClW Chloro                                                     NH2W Amino

                 BrW Bromo                                                    CNW Cyano

                IW Iodo                                                                                




                                                        - ١٧ -
    ‫א‬‫א‬                                    ١٤٠                                      ‫א‬
 ‫א‬‫א‬                        ‫א‬‫א‬                         ‫א‬



                                                                                                               W
                                                        Br
                                             5    4          2     1
                                            CH3CHCHCH 2CH3
                                                        3
                                                  CH3        Cl
                                  3-Bromo-2-chloro-4-methylpentane
                                                                                                           
                                                                 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬‫א‬neo-‫א‬iso-
                                        
‫א‬‫א‬tridisec-tert-‫א‬‫א‬‫א‬
                                                                                                       K‫א‬


                                                                    W‫א‬‫א‬‫א‬‫א‬٢J ٢J ٢
‫א‬،nonpolar‫א‬                       
               
‫א‬،‫א‬‫א‬‫א‬‫א‬C4C1،‫א‬‫א‬
١٨‫א‬‫א‬‫א‬‫א‬، C17C5
                                                                   
،‫א‬‫א‬،‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
                       
‫א‬‫א‬،‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬
                                                                                K‫א‬


                                                                   W‫א‬‫א‬‫א‬٢J ٢J ٣
‫א‬‫א‬،‫א‬‫א‬
                                                              W‫א‬‫א‬


                                                                            Wcombustion ‫א‬‫א‬               -١
–‫א‬‫א‬‫א‬
                       K‫א‬K‫א‬‫א‬‫א‬

                                                        - ١٨ -
   ‫א‬‫א‬                                   ١٤٠                                    ‫א‬
 ‫א‬‫א‬                        ‫א‬‫א‬                     ‫א‬



                 CH4 + 2O2                              CO2 (g) + 2H2O + ‫ﻃﺎﻗﺔ‬
                                                                     (g)
                                                                            WHalogenation‫א‬       -٢
،‫א‬Br2‫א‬Cl2‫א‬E‫א‬‫א‬F‫א‬
                                                                         
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
                                                                      W‫א‬‫א‬،


                                                                                                 WE١F
                                                                            Br

                                   + Br2                                           + HBr

                                                                    Bromocyclopentane
                                                        


                                                                                                 WE٢F
                     H
                                             hν
         H           C       H + Cl2                         H3C _ Cl + HCl
                     H                                      Chloromethane
                                        hν              
         CH3 Cl + Cl2                                  CH2Cl2 + HCl
                                                Dicarbomethane
                                                                                                    
                                        hν
                                       hv
         CH 2Cl2 + Cl2                               CHCl 3 + HCl
                                                     Chloroform
         
                                   hν



                                                        - ١٩ -
   ‫א‬‫א‬                              ١٤٠                                         ‫א‬
 ‫א‬‫א‬                   ‫א‬‫א‬                          ‫א‬


                                 hv
         C H Cl 3 + Cl2                    C C 14 + HCl
                                      Carbontetrachloride
                                                        '
،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬
                                                                                                 W


                                                                       K‫א‬EF‫א‬‫א‬           K 
                                               
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                  K‫א‬‫א‬
                                                                                                          

                                          H 2 /Pt ,Pd ‫ أو‬Ni                 _    _      _
                             C    C                                             C C
                                                 ‫ﺿﻐﻂ‬
                                                                                H H

                            Alkene                                          Alkane
                                                                                                                 
                                                    H2 , Pt
        CH3CH2CH2CH2CH = CH 2                                         CH3CH2CH2CH2CH2CH2
                                                     ‫ﺿﻐﻂ‬
              1- Hexene                                                         n- Hexane

                                                                                      W K
                                                                     
،‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬KGrignard reagents ‫א‬
                                                                                         K‫א‬‫א‬
                                                                                                          
                                            ‫اﻳ ﺜﺮ ﺟ ﺎف‬
                         R-X + Mg                                 RMgX

                      Alkyl halide                         Alkyl magnesium halide 
                                                   - ٢٠ -
   ‫א‬‫א‬                                    ١٤٠                                   ‫א‬
 ‫א‬‫א‬                         ‫א‬‫א‬                    ‫א‬



                                                                                                          
‫א‬‫א‬‫א‬‫א‬
                                                                                      K‫א‬‫א‬
                            R-MgX + H 2O                                    RH + Mg(OH)X
                                                                     Alkane
                       RMgX+CH 3OH                                    RH + Mg(OCH 3)X
                                                                   Alkane
                            Br                                                   Mg Br
                                                   ‫اﻳ ﺜﺮ ﺟ ﺎف‬
                      CH3CH2CHCH 3+Mg                                CH3CH2CHCH 3

                                    Mg(OH)Br + CH 3CH2CH2CH3                                H2O
          

                                                                                        W K
                                  K‫א‬‫א‬‫א‬
                                                                                                          
                                2R - X + 2 Na                               R - R + 2 NaX
                                                                           Alkane

                       2 CH 3 CH2 Cl + 2 Na                                 CH3 CH2 CH2 CH3


                                                                W‫א‬‫א‬‫א‬‫ א‬K
                                                    
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                    ،‫א‬‫א‬‫א‬
           W‫א‬‫א‬Lithium dialkyl copper ( R2CuLi)
                                               
                      (CH 3 CH2)2 CuLi + CH 3 CH2 CH2 Br

                                     CH3 CH2 CH2 CH2 CH3 + CH3 CH2 Cu + LiBr

                                                         - ٢١ -
   ‫א‬‫א‬                             ١٤٠                                ‫א‬
 ‫א‬‫א‬                  ‫א‬‫א‬                 ‫א‬



                                                  
                                       W‫א‬‫א‬‫א‬‫א‬

                          CH 3 CH2 Cl + Li                          CH 3 CH2 Li
                                                                                            

             2 CH 3 CH2 Li + Cul                                (CH 3 CH2)2 CuLi + Lil

                                                       W‫א‬٢J ٢J ٤
K‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                   
K‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬٪٨٠‫א‬
               K‫א‬،‫א‬‫א‬
                   
‫א‬‫א‬KRefining‫א‬‫א‬
                                                                                      K
                                                                                                    
                                                                                                    
                                                                                                    
                                                                                                    
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                                                  - ٢٢ -
   ‫א‬‫א‬                                ١٤٠                                        ‫א‬
 ‫א‬‫א‬                     ‫א‬‫א‬                        ‫א‬



                                                                Walkenes‫א‬٢J ٣
،EC=CF–‫א‬ ‫א‬
،CnH2n‫א‬‫א‬‫א‬،olefins
                                    KC2H4‫א‬‫א‬CnH2n-2‫א‬
                                                     
                                       H         120                    H
                                                 C       =    C
                                      H                                H
                                                     
                                                     
                                                                             W‫א‬٢J ٣J ١


                                                                                        W‫א‬‫ א‬K
         
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                           
،‫א‬‫א‬–ylenealkane‫א‬‫א‬‫א‬‫א‬–ane
                                                                           W‫א‬‫א‬

                          K‫א‬‫א‬E1-3-2F

                     Alkene‫א‬                                         Alkane‫א‬

            Ethylene            CH 2=CH 2                               Ethane        CH3CH3

        Propylene              CH3-CH =CH2                                        
                            
                                                                    Propane           CH 3CH 2CH 3
          Butylene              CHCH2CH=CH2
                                 3                                                 
                                                                                   
     B-Butylene                CHCH=CHCH
                                 3       3
                                                                  n-Butane       CH 3CH 2CH 2CH 3
           Isobutylene CH3 CH = CH2                                Isobutane       CH3 CH CH3

                                   CH3                                                   CH3
                                                     - ٢٣ -
   ‫א‬‫א‬                                  ١٤٠                                 ‫א‬
 ‫א‬‫א‬                       ‫א‬‫א‬                  ‫א‬



– CH2=CH2‫א‬‫א‬‫א‬‫א‬
                                             W( Vinyl group )‫א‬CH=CH2
                                                                                                          
             CH2 = CH                       CH 2 = CH                        CH2 = CH

                         Cl                              Br
        Vinyl Chloride
                        Vinyl bromide 
                                                   Vinyl Cyclohexane
                                                                   
      W( allyl group)‫א‬CH3CH=CH2‫א‬‫א‬‫א‬
                                       CH2CH = CH2
                                       Cl
                                             Allyl Choride

                                                                           WIUPAC‫א‬‫ א‬K
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                           
 ‫א‬E ‫א‬‫א‬FIUPAC‫א‬
                                         W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                          KE‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬ E١
                                
–‫א‬‫א‬‫א‬‫א‬–ane‫א‬‫א‬‫א‬‫א‬ E٢
                                                                                                 Kene
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬ E٣
                                                                          K‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                   W‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                                                                          



                                                       - ٢٤ -
    ‫א‬‫א‬                                          ١٤٠                                               ‫א‬
 ‫א‬‫א‬                                ‫א‬‫א‬                              ‫א‬


                                             5        4      3        2     1
                                             CH3CH-CH = CH-CH 3

                                                     CH3
                                                      4- Methyl - 2- Pentene
                                                                                                                               
                                                                                    W‫א‬‫א‬‫א‬
                                                                                                 CH3CH2CH = CH2
                 CH2 = CH2                             CH 3 -CH = CH               2                   1-Butene
                      Ethene                                 Propene                                      
                                                
                                                                                                          
                                                                                              CH2-CH = CH2

                                                                                               Cl
                                                                                            3-Chloro -l- Propene
                                2-Ethyl-1-Butene                                                   
                                                                                                                               
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                            
‫א‬K‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                         K‫א‬‫א‬‫א‬‫א‬‫א‬
                                 6
                                                                                               3
                           5         1                                                 4            2
                           4         2
                                 3                                                     5            1
                                                                                               6
                      Cyclohexene                                            3-Methylcyclohexene
                  (1-Cyclohexene‫)وﻟﻴﺲ‬                                     (6-Methylcyclohexene ‫)وﻟﻴﺲ‬

–ene‫א‬‫א‬‫א‬‫א‬KKKKKKtetra،tri ،di ‫א‬
‫א‬‫א‬‫א‬‫א‬
                                                                                       K‫א‬‫א‬‫א‬‫א‬
                                                                                                                               


                                                                 - ٢٥ -
    ‫א‬‫א‬                                             ١٤٠                                                 ‫א‬
 ‫א‬‫א‬                                  ‫א‬‫א‬                                   ‫א‬



                                                                 
                               4       3       2
                                                                                                             5
                       5
                       CH2 = CH-CH 2-C-CH 2CH3                                                     1             4
                                           1 CH 2
                                                                                                     2           3
                          2-Ethyl,1,4-Pentadiene                                    1,3-Cyclopentadiene
                                                                                                    
                                                                                                                               
                                                                2         4          6
                                                          1           3       5              7
                                                             1,3,6-Heptatriene 
                                                                                                                               
‫א‬F‫א‬‫א‬‫א‬‫א‬                                                     
                     
‫א‬E2-butane 1-butene‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
                                                              W2-butene
                                                                                                                              
                           H                       CH3                                           CH3                 CH3

                                   C       C                                                             C       C
                                                                                                 H               H
                        CH3             H
                                                                                                    Cis-2-butene 
                        trans-2-butene                                                                              
                                                                                                                               
E‫א‬‫א‬‫א‬‫א‬F‫א‬‫א‬
F‫א‬‫א‬،E–cisF‫א‬،‫א‬
                                                 
،‫א‬‫א‬Ktrans‫א‬E‫א‬
trans-2- ٣٧،‫א‬،cis-2-butene ،‫א‬‫א‬‫א‬
                                                                                                                          
                                                                                                                          
                                                                                                                      K ٠{٩butene




                                                                     - ٢٦ -
    ‫א‬‫א‬                               ١٤٠                                          ‫א‬
 ‫א‬‫א‬                     ‫א‬‫א‬                           ‫א‬



                                                                W‫א‬‫א‬‫א‬٢J ٣J ٢
                                                                             
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
،‫א‬،‫א‬،‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬ ‫א‬
                                                                    
‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                                                                       K‫א‬


                                                                         W‫א‬٢J ٣J ٣
                                                 W‫א‬‫א‬
                                                                    W‫א‬‫א‬‫א‬‫א‬          E٤
‫א‬‫א‬‫א‬‫א‬،H+،‫א‬
                                       KH3PO4‫א‬H2SO4‫א‬‫א‬
                                                                                                          
                        H     H                               H                     H
                                          +
                                        H ,
              H        C      C    H                                C     C             + H2O
                       OH H                                   H                     H

                      (‫آﺤﻮل )اﻳﺜﺎﻧﻮل‬                               (‫اﻟﻜﻴﻦ )اﺛﻴﻠﻴﻦ‬
          

                              
‫א‬F‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                 
،‫א‬‫א‬E‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                            W‫א‬‫א‬
                                         +
                                       H ,
          CH2         CH      CH CH3                      CH3-CH = CHCH3
          H                                                    2-Butene
                      OH       H

              2-Butanol                               +                                 + H2O


                                                           CH3=CHCH2CH3
                                                               1-Butene
                                                     - ٢٧ -
    ‫א‬‫א‬                                 ١٤٠                                          ‫א‬
 ‫א‬‫א‬                       ‫א‬‫א‬                          ‫א‬




                                            W‫א‬‫א‬‫א‬‫א‬                   E٥
  KKOH‫א‬‫א‬( I , Br, Cl =X ) HX 

                                      KOH / ‫آﺤﻮل‬                                  +     -
                      CH2    CH2                            CH2 = CH2 +K +CI +H2O

                         H   Cl                                  ‫اﺛﻴﻠﻴﻦ‬

                ‫آﻠﻮرو اﻳﺜﺎن‬                                         
                                                    
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
                                                           W‫א‬‫א‬،‫א‬
                                                                                                            
                                                                                                            
                                                KOH / ‫آﺤﻮل‬
          CH2         CH     CH     CH3                                   CH3     CH = CH        CH3 + K+
          H           Br     H
                                                                                                
         J ٢EFJ ٢
                                                                                                            
                                                         H+Br-+H2o
                                                                                                  
                                                                         CH2 = CHCH2CH3

                                                                                                                

                                                                          EFJ ١
                                               W‫א‬ H2SO4‫א‬‫א‬ K١
‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                        
‫א‬K‫א‬‫א‬ ‫א‬‫א‬‫א‬،‫א‬
                                                                                               K
                                                                                                 


                                                       - ٢٨ -
    ‫א‬‫א‬                                ١٤٠                                          ‫א‬
 ‫א‬‫א‬                      ‫א‬‫א‬                         ‫א‬


            CH2 = CH2 + H2SO4 ‫ﻣﺮآﺰ‬                   CH2        CH2

                                                   H         OSO3H
                                          ‫آﺒﺮﻳﺘﺎت اﻻﻳﺜﻴﻞ اﻟﻬﻴﺪروﺟﻴﻨﻴﺔ‬                
                                                                                                          
                                                                           WPolymerization‫ א‬K٢
                                                                          
‫א‬––‫א‬
                                                                        
،‫א‬‫א‬‫א‬‫א‬ Kpolymers‫א‬
                                       K‫א‬‫א‬‫א‬‫א‬


                                                                   W‫א‬‫א‬W
 
‫א‬Naphtha fraction‫א‬‫א‬‫א‬‫א‬         
١٠J ٤‫א‬‫א‬‫א‬‫א‬،‫א‬
،٩٠٠J ٧٠٠‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                    K‫א‬‫א‬‫א‬‫א‬‫א‬
                                                           
‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬
                                                                         K‫א‬‫א‬
،ECr2O3+Al2O3) ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                          K‫א‬‫א‬


                                               Cr2O3 +Al2O3
                           CH3CH2CH3                                        CH2 = CHCH3
                                                      700cْ                                    
                                                                                                       
                                                                                                      
                                                    W( X = Cl ,Br, I ) HX‫א‬
                                                                                                  




                                                      - ٢٩ -
    ‫א‬‫א‬                                          ١٤٠                                                 ‫א‬
 ‫א‬‫א‬                                ‫א‬‫א‬                                 ‫א‬




                                     C        C         + HX                              C      C
                                                                                           H X
                                                                                        ‫هﺎﻟﻴﺪ اﻟﻜﻴﻞ‬      
                                                                                                                           
                                      CH2=CH2 + HCI                                CH 3     CH2 CI
                                                                          (‫آﻠﻮرو اﻳﺜﺎن )آﻠﻮرﻳﺪ اﺛﻴﻞ‬                 
                                                                                                                                    
‫א‬،‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                       K‫א‬‫א‬Markovnikov's Rule 
                                CH2 = CHCH3 + HCl                             CH2          CH        CH3

                                                                               H          Cl
                                                                                                                            
                               J ٢
                                                                                                                                    
                                                                                                WHydration ‫א‬
‫א‬K‫א‬H+‫א‬‫א‬‫א‬
                                                                              
                                                                                                    K
                                                                     +
                                                                 H
                              CH2 = CHCH3 + H2O                             CH2           CH     CH3

                                                                        H             OH            
                                                                                                                             
                                      J ٢
                                                                                                                                    




                                                                - ٣٠ -
    ‫א‬‫א‬                                   ١٤٠                                        ‫א‬
 ‫א‬‫א‬                         ‫א‬‫א‬                         ‫א‬



                                                                   W‫א‬٢J ٣J ٤
‫א‬K،‫א‬‫א‬‫א‬
                                                                        W‫א‬K‫א‬‫א‬


                                                                             WHydrogenation‫١. א‬
  K‫א‬CatalystsE‫א‬FPdNi Pt ‫א‬‫א‬
                                                           Pt or Ni
                                 CH2 = CH2 + H2                                 CH3 CH3
                                    ‫اﺛﻴﻠﻴﻦ‬                                      ‫إﻳﺜﺎن‬
                                                                                                                       
،‫א‬‫א‬‫א‬،‫א‬‫א‬
                                                   ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬


                                                                              WHalogenations‫٢. א‬
                                             
‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                           K‫א‬
                                                                                              

                                 C      C     +    X2 / CCI4                         C   C

                                    (X = CI , Br)                      X   X      
                                                                                                           
                           CH2 = CH2 + Br2 / CCI4                              CH2       CH2

                                                                Br       Br 
                                                                                             
،E–‫א‬‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                     
                                                                     K‫א‬‫א‬‫א‬
                                                                                                                   

                                                         - ٣١ -
   ‫א‬‫א‬                               ١٤٠                                   ‫א‬
 ‫א‬‫א‬                    ‫א‬‫א‬                    ‫א‬



                                                                                WAlkynes‫א‬٢J ٤
 J F–‫א‬ ‫א‬  
‫א‬‫א‬،CnH2n-2‫א‬‫א‬KEJ C C
،‫א‬sp‫א‬‫א‬،‫א‬‫א‬،C2H2‫א‬
‫א‬K‫א‬‫א‬
                                      
‫א‬‫א‬‫א‬،٣٠٠٠‫א‬‫א‬‫א‬
                                                                                          K‫א‬
CaO‫א‬‫א‬‫א‬
                                       K‫א‬CaS2‫א‬،

                                                 2500 oC
                                3C + CaO                        CaC2 + CO

                          CaC2 + 2H2O                         C2H2 + Ca(OH) 2



                                                                    W‫א‬٢J ٤J ١
                        
EIUPAC‫א‬F‫א‬‫א‬‫א‬ ‫א‬
‫א‬‫א‬،‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،
                                   W‫א‬‫א‬–ene ‫א‬–yne‫א‬

             HC          CH        CH3C         CH             CH3CH2C         CH

            Acetylene           Methyl acetylene               Ethyl acetylene       


               Ethyne                                                  1- Butyne    
                                            Propyne

                                                                                                         

                                                    - ٣٢ -
    ‫א‬‫א‬                                ١٤٠                                      ‫א‬
 ‫א‬‫א‬                      ‫א‬‫א‬                       ‫א‬



                                                                          WIUPAC‫א‬‫א‬


                                              CH3                                   CH3
         CH3C            CCH3
                                         CH3CH CH                  C       C CH2CH CH3
               2-Butyne
                                                        Cl
                                                 3-Chloro-2,7-dimethyl-4-octyne

                                          CH        C          C     CH
                                                1,3-Butadiyne
                                                                                                              
                                                                   
‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬–yne‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬،‫א‬
                             Kalkene‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬

                                      HC      CH CH2 CH CH2

                                               1-Penten-4-yne

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                    K‫א‬–yne ‫א‬


                                                       W‫א‬‫א‬‫א‬٢J ٤J ٢
                                               
‫א‬‫א‬‫א‬‫א‬ ‫א‬
‫א‬،‫א‬K‫א‬‫א‬
C17‫א‬C16C4 ‫א‬،‫א‬C4C2
                                                                                                 K‫א‬




                                                      - ٣٣ -
   ‫א‬‫א‬                              ١٤٠                                      ‫א‬
 ‫א‬‫א‬                   ‫א‬‫א‬                       ‫א‬



                                                                               W‫א‬٣J ٣J ٤
                                   
‫א‬‫א‬‫א‬‫א‬
                                                                            W‫א‬‫א‬‫א‬


                      Dehydrohalgenation W‫א‬‫א‬‫א‬‫א‬ .١

         W
                                                                                               
                                                 KOH
                          CH3CH CH H                            [ CH3CH = C         H]
                                                 EtOH
                              Br Br                                            Br
                          1,2-Dibromopropane                          Allylbromide


                                                                NaNH2 /
                            CH3 C      C     H
                                Propyne
                                                                                               


                                                           W‫א‬‫א‬ .٢
 W‫א‬‫א‬‫א‬‫א‬


                      -                    liq NH 3
        HC           C Na+ + CH3Br                          HC         C    CH3 + NaBr


                      -                      liq NH3
        HC           C Na+ + CH3CH2I                          HC        C CH2CH3 + NaI

                          -               liq NH
       CH3 C             C Na+ + CH3CH2Br       3
                                                                CH3 C          C CH2CH3 + NaBr
         Sodium propynide


                                                   - ٣٤ -
   ‫א‬‫א‬                                 ١٤٠                                 ‫א‬
 ‫א‬‫א‬                      ‫א‬‫א‬                  ‫א‬



                                                         
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                      K‫א‬‫א‬‫א‬‫א‬


                                           W‫א‬‫א‬‫א‬‫א‬
                                                              
‫א‬‫א‬‫א‬‫א‬‫א‬
                            W‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬W‫א‬‫א‬‫א‬ J ١
                                W‫א‬‫א‬‫א‬‫א‬


                         CH4 + O2                  2HC          CH + 2CO + 10H2


‫א‬‫א‬‫א‬‫א‬W‫א‬ J ٢
،‫א‬‫א‬‫א‬‫א‬،‫א‬
E‫א‬F‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬
                                                                                         W‫א‬


                                   CaCO3                       CaO + CO2

                                                           Calcium carbonate

                                                     2500
                                  CaO + 3C                        CaC2 + CO
                                             Coke                 Calcium carbide

                                               ْ
                                               25C
                            CaC2 + 2H2O                     HC           CH + Ca(OH)2
                                                               Acetylene



                                                      - ٣٥ -
   ‫א‬‫א‬                                   ١٤٠                                     ‫א‬
 ‫א‬‫א‬                        ‫א‬‫א‬                      ‫א‬



                                                                          W‫א‬٢J ٤J ٣
                                                    W‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
    W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K


                                                                                  W‫א‬ .١
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                      K‫א‬‫א‬،‫א‬

                                                         R                 R
                                           Pd or Ni                            H2\Ni
            R        C     C    R + H2                        C=C                       RCH2CH2R
                                                         H                 H
                                                                                                            
                                                                   
Ni-‫א‬‫א‬‫א‬‫א‬
Linders         catalyst       Pd + Pb(OAc)4‫א‬‫א‬‫א‬B2
                                                                                             KPd/CaCO3)


                                                                                    W‫א‬‫٢. א‬
 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                   W‫א‬‫א‬


                                                                 Cl                        Cl Cl

      CH C C CH + Cl2
        3      3                                CH C = C CH
                                                  3        3                           CH C C CH
                                                                                         3      3

                                                          Cl                               Cl Cl
                                                                                1,1,2,2-Tetrachlorobutane




                                                        - ٣٦ -
   ‫א‬‫א‬                                ١٤٠                                        ‫א‬
 ‫א‬‫א‬                     ‫א‬‫א‬                        ‫א‬



                                                                         W‫א‬‫א‬ .٣
‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬،
 K‫א‬‫א‬‫א‬‫א‬‫א‬


                                                                                       Cl
                                    HCl                                  HCl
             CH3 C           CH              CH3C = CH 2                        CH3 C         CH3
                                                    Cl                                  Cl
                                                                                  2,2-Dichloropropane



                                                                                      W‫א‬ .٤
‫א‬‫א‬‫א‬‫א‬
‫א‬،mercuric sulfate ‫א‬
                                                    K‫א‬‫א‬

                                                                                             O
                                               H                 H
                                    HgSO4
            CH           CH + H2O                    C=C                            CH3 C            H
                                    H2SO4
                                               H                 OH

                                                      Enol                                  Acetaldehyde

                                                              OH                                 O
                                     HgSO4
    CH3 C                CH + H2O                  CH3        C = CH2                  CH3 C             CH3
                                     H2SO4


                                                                                          Acetone



                                                     - ٣٧ -
    ‫א‬‫א‬                                     ١٤٠                                           ‫א‬
  ‫א‬‫א‬                          ‫א‬‫א‬                            ‫א‬



                                                                                    W‫א‬ .٥
                             
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬
                                                      W‫א‬‫א‬


                                                                          O O
                                                              -
                                          1)KMnO4 /OH
                                                      -             R     C    C      Rَ
                                           2)H2O / OH
                                                                          O                       O
                                                              -
                                           1)KMnO4 /OH
              R       C    C      Rَ                                R     C    OH + Rَ C                 OH
                                           2) 100C / H +
                                              ْ


                                           1)O3
                                                                     RCOOH                 C
                                                                                        + Rَ OOH
                                           2)H2O /Zn Or H2O2




                                        ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬٢J ٤J ٤
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                              
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬
                                                
‫א‬‫א‬(PVC) ‫א‬‫א‬
‫א‬‫א‬A‫א‬‫א‬‫א‬‫א‬
                                                                     K‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                     KPayragyline ‫א‬‫א‬
                                                                                                                     
                                                                                                                            
                                                                                                                            
                                                                                                                            
                                                                                                                            
                                                                                                                            
                                                                                                                            

                                                           - ٣٨ -
  ‫א‬‫א‬                              ١٤٠                                     ‫א‬
‫א‬‫א‬                   ‫א‬‫א‬                      ‫א‬



                                     2-5
                                                  
                           WIUPAC‫א‬‫א‬‫א‬‫א‬J ١
                                                                                                         
               CH3CHCHCHCH 3
                                                  -‫ب‬           CH3-C(CH3)2CH3                    J 
                       Br Cl CH3
                                                                         CH3
           CH3CH2CH2 C = CH2
                                                  J                                            J 

                                                                               C2H5
                                                                 CH3
                                                  J                    CH C      CH             J 
                                                                     CH3
                                                                     CH3 C = C    CH3
                                                                                                  J 
                                                                         CH3 Br
                                                                                                         
                                                                                                         
                                           W‫א‬‫א‬‫א‬‫א‬‫א‬–٢
                                                                                                          
                                             
              2-bromo-2-methyloctane                                    2,3-dimethylbutane J 
                                             J
      2-chloro-3-methyl-2-pentene J      1,1-dimethylcyclohexane J 
            2,2-Dibromo-3-hexyne J  2,3Dimethyl-1,4-cyclohexadiene J 


       ‫؟‬‫א‬C6H14‫א‬‫א‬‫א‬‫א‬‫א‬–٣
                                                                                                         
                                        ‫؟‬‫א‬‫א‬‫א‬‫א‬‫א‬–٤



                                                  - ٣٩ -
  ‫א‬‫א‬                                      ١٤٠                                 ‫א‬
‫א‬‫א‬                       ‫א‬‫א‬                      ‫א‬



                                                                             W‫א‬‫א‬–٥

    CH3CH3 + Cl2                    hυ
                                                                                                      J 

    CH4 + 2O2                                                                                        J 
    CH3CH2Cl + Na                                                                                    J 

    CH3CH2OH                H+,∆
                                                                                                     J 


    CH3CH=CH2                Pt or Ni
                                                                                                     J 
                                          CCl
    CH3CH=CHCH3 + Br2                           4                                                     J 
                               CCl4
                    + Cl2                                                                             J 

                                   KOH                      NaNH2 /
   CH3CH CH CH3                                                                                       J 
                                   EtOH

      Br Br
   CH3 C C CH3 + 2Cl2                                                                                J 

                            HgSO4
   CH3 C            CH                                                                               J 
                            H2SO4


                                                     W،–٦
                                                                                                             
        i) CH3CH3                          ii) CH3CH2Cl                       iii) CH2 = CH2

                                    W‫א‬‫א‬‫א‬–٧
                        3-Bromo-1-pentyne ,                       4-Methyl-2-hexene

                                                                                       W‫א‬‫א‬‫א‬
                                           H2 , Br2/H2O , H2O/H+ , HCl

                                                        - ٤٠ -
  ‫א‬‫א‬                               ١٤٠                                          ‫א‬
‫א‬‫א‬                    ‫א‬‫א‬                           ‫א‬



                                     ٢J ٥‫א‬
                                                                                                           W١
                                                                            2,2- Dimethyl Propane -‫ا‬               .١


                                                              3-Ethyl-1-Methyl cyclohexane -‫ﺟـ‬                     .٢


                                                                             3-Methyl -1- butyne -‫هـ‬               .٣


                                                                       2- Bromo -3-Methyl -2- buteneJ 

                                                                                                               
                                                                                                          W٢
                                                                                                                .٤
                                                                                  CH3 - CH -CH -CH3

                                                                                         CH3 CH3                .٥
                                                                            CH 3 C       C     CH 2CH 3
                                                                                   Cl CH 3                      .٦
                                                                                   Br
                                                                            CH 3 C       C     CH 2CH 3
                                                                                    Br      .٧
                         K‫א‬‫א‬‫א‬‫א‬W٤
                                                                                                          W٥
                                  CH4 +2O 2               CO2 + 2H2O + ‫ﻃﺎﻗﺔ‬              .٢ J  K١
                                                     +
                                 CH3 CH2 OH
                                                   H ,
                                                               CH2 = CH2 + H2O .٤             J  K٣
                                                   CCI4
              CH3 - CH = CH - CH 3 + Br2                      CH2CH - CH CH 3
                                                                                              J  K٥
                                                                       Br    Br          .٦

                                                   - ٤١ -
                                              ‫א‬‫א‬‫א‬
                                           ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                               ‫א‬‫א‬‫א‬‫א‬




                      ‫א‬‫א‬
                         ‫א‬‫א‬
 ‫א‬‫א‬




٣
   ‫א‬‫א‬                               ١٤٠                                    ‫א‬
  ‫א‬‫א‬                      ‫א‬‫א‬                     ‫א‬



                                                                                                 W‫א‬‫א‬
                                                          
،‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                        K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬


                                                                                        W‫א‬‫א‬
                                                    W‫א‬‫א‬‫א‬
                                 K‫א‬‫א‬ .١
                                                     K‫א‬‫א‬ .٢
                                            K‫א‬‫א‬‫א‬‫٣. א‬
                                                                K‫א‬‫א‬ .٤


                                                                                 W‫א‬‫א‬‫א‬
                                                      K٪٩٠‫א‬‫א‬‫א‬


                                                                                    W‫א‬‫א‬
                                                                                             K٤


                                                                               W‫א‬‫א‬
                                                 KOverhead Projector .١
                                                              K‫א‬‫א‬‫א‬‫א‬‫א‬ .٢
                                                                                       K .٣


                                                                                       W‫א‬‫א‬
                                                                        K‫א‬‫א‬‫א‬‫א‬




                                                    - ٤٢ -
    ‫א‬‫א‬                                ١٤٠                                     ‫א‬
  ‫א‬‫א‬                        ‫א‬‫א‬                      ‫א‬



                                                                                 W1J 3
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                           
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
                         
‫א‬
                                   K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
E‫א‬‫א‬‫א‬‫א‬F‫א‬EAromatic) ‫א‬‫א‬
،J OCH3 ‫א‬‫א‬‫א‬
          
J C6H5‫א‬‫א‬J J J J J COOCH3،J COOH
،J C6H5‫א‬‫א‬‫א‬
                                                               
EF‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
                                                                K‫א‬‫א‬


                                                                        W‫א‬2J 3
‫א‬‫א‬‫א‬‫א‬‫א‬C6H6‫א‬
                                                                     
                                                                                  
‫א‬،‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬K‫א‬sp2‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬، (A˚١٣٩F‫א‬‫א‬–
                                                                                    
‫א‬‫א‬KE١٥٤A˚)C-C‫א‬‫א‬‫א‬،E١٣٢A˚)C=C
                                                      WKekule ‫א‬‫א‬



                              
                                   I               II
      
‫א‬Hybrid‫א‬‫א‬KII،I‫א‬
                                                 
‫א‬‫א‬‫א‬‫א‬KII،I
                                                                                 Delocaized



                                                      - ٤٣ -
    ‫א‬‫א‬                                    ١٤٠                                     ‫א‬
  ‫א‬‫א‬                            ‫א‬‫א‬                      ‫א‬




                                                                              W‫א‬‫א‬3J 3
                                            W‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬ K١
FP‫א‬‫א‬‫א‬EF
                                                                             KE‫א‬
                                                                    K‫א‬ K٢
                             K‫א‬‫א‬‫א‬ K٣
‫א‬‫א‬‫א‬EHuckels ruleF K٤
En = 0,1,2,3KKKKKKKFE4n+2)‫א‬‫א‬π‫א‬‫א‬
‫א‬Eπ‫א‬F‫א‬‫א‬
                       WE٦F‫א‬‫א‬E١Fn‫א‬
                                                           
                                                       (4x1+2) = 6

E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                          W‫א‬
                                                                                                                 



                                          
                            Benzen                Naphthalene                     Anthracene
                             n =1                   n =2                            n =3




                                                          - ٤٤ -
    ‫א‬‫א‬                                   ١٤٠                                              ‫א‬
  ‫א‬‫א‬                           ‫א‬‫א‬                               ‫א‬




                                                                                              ..
                                                         N                                    N
                                                        ..                          
                                                      Pyridine                               Pyrole
                        Phenanthrene                                                       n =1
                                                      n =1
                                                                                         4(1)+2=6 πes
                             n=3                   4(1)+2=6 πes
                 4(3)+2=14 πes
                                                                                              +
                                +                          -


                                              
                              n=0                    n =1                      
                           4(0)+2=2 πes                                               n =1
                                                   4(1)+2=6 πes
                                                                                 4(1)+2=6 πes


                                                                             W‫א‬‫א‬‫א‬
                                                                                                                         
                                          -                                                              +




                                                                          W‫א‬‫א‬‫א‬4J 3
                                                                  
‫א‬‫א‬º٨٠K ‫א‬،‫א‬‫א‬
                                        
‫א‬‫א‬‫א‬‫א‬º٤{٥

                                                        Kπ‫א‬‫א‬‫א‬




                                                         - ٤٥ -
   ‫א‬‫א‬                              ١٤٠                                      ‫א‬
  ‫א‬‫א‬                    ‫א‬‫א‬                        ‫א‬



                                                                   W‫א‬4J 3
                                          
‫א‬‫א‬‫א‬‫א‬
                                                       W‫א‬
              W‫א‬‫א‬‫א‬‫א‬‫א‬ K١
            W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                           

                          Br                         I                               CH2CH3


                                                                         
                 Bromobenzene                  Iodobenzene                     Ethylbenzene
                          NO2



                 
                     Nitrobenzene
                                                             W‫א‬

                        CH3           CH=CH2 CH _ CH _ CH                                CHO
                                               3         3



                                                                                
                     Toluene          Styrene               Cumene                  Benzaldehyde

                                                                 O
                        OH             COOH                                              NH2
                                                                 C _ CH3


                                                                                
                      Phenol        Benzoic acid                                      Aniline
                                                           Acetopnenone

                                                  - ٤٦ -
    ‫א‬‫א‬                                   ١٤٠                                        ‫א‬
  ‫א‬‫א‬                           ‫א‬‫א‬                         ‫א‬



                                  SO3H                                                OCH3



                                                                               
                                                                                    Anisole
                       Benzenesulfonic acid
                
‫א‬،‫א‬‫א‬‫א‬‫א‬
                K‫א‬‫א‬‫א‬‫א‬‫א‬phenyl
                                                                                                                   

                            CH3CHCH2CH3                                             CH2CH2OH


                                                                           
                            2-Phenylbutane                                     2-Phenylethanol
                                                                                                             
Benzyl‫א‬‫א‬‫א‬
                             
‫א‬‫א‬‫א‬، Benzal‫א‬‫א‬
                                                                                                           KBenzo
                                                                                                             
                            CH2Cl                         CHCl2                               CCl3



                                                                                    
                    Benzylchloride             Benzalchloride                       Benzotrichloride
                                                                                                                   
         ‫א‬ K٢
        ortho EOF‫א‬‫א‬‫א‬K‫א‬‫א‬
        ‫א‬  meta EmF ‫א‬ ‫א‬    ‫א‬ ‫א‬ 

                                                         - ٤٧ -
  ‫א‬‫א‬                                             ١٤٠                                                 ‫א‬
 ‫א‬‫א‬                                  ‫א‬‫א‬                                    ‫א‬



        ‫א‬   K  para Ep F ‫א‬ ‫א‬   ‫א‬
       K Benzene ‫א‬ K‫א‬‫א‬
         W‫א‬‫א‬،‫א‬‫א‬،‫א‬
                                                                                                               F
                      CI                                       CH2CH3
                           CI


                                                               CI
                                                                                                            I
      O-dichlorobenzene                           m-chloroethylbenzene                            p-fluoroiodobenzene
                    CH 3                                        COOH                                           OH
                                                                                                                    CI

                          NO 2                                                                        
                                                      Br
             m-nitrotoluene                        m-bromobenzoic acid                                  o-chlorophenol

                                           W‫א‬‫א‬CH3-
                       CH3                                        CH3                                          CH 3
                             CH3


                                                                        CH3                               CH 3
                   o-xylene                                  m-xylene                                  p-xylene
                             ‫א‬‫א‬
                                      CI                                                           NO2
                                          2
                                                                                                   1
                           CI 1               CI                                           6             2
                                              3
                                                                                       5                 3
                             6                4                                                           CI
                                                                                       F
                                     5                                                           4

                                                                                              
                   1,2,3-trichlorobenzene                             3-chloro-5-fluronitrobenzene
                                                                ‫א‬F
               (1,2,6-trichlorobenzene)                                           E١‫א‬
                                                                                              

                                                                - ٤٨ -
  ‫א‬‫א‬                                        ١٤٠                                             ‫א‬
 ‫א‬‫א‬                               ‫א‬‫א‬                              ‫א‬


                                    OH                                                      CH3
                                                                                            1
                           Br             Br                                    NO2                 NO2
                                                                                    6             2
                                                                                    5           3
                                                                                            4
                                   Br                                                      NO2
                                                                                       
                      2,4,6-tribromophenol                              2,4,6-trinitrotoluene (TNT)
          ‫א‬)                        ‫א‬F
                           E١‫א‬                                      E١‫א‬
                                                                                                                           


                                                                    W‫א‬‫א‬٣J ٦
                                     
       ،‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
                       
       ‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
       ‫א‬‫א‬‫א‬‫א‬‫א‬
       ‫א‬‫א‬‫א‬‫א‬‫א‬
       ‫א‬،
                                                                                                 K‫א‬
                                          _
                                     Al2O3 CrO3 / 500ْ C
                                                                                CH3

        CH3(CH2)5CH3                                                                        + 3H2
                                          Pt / 400ْ C

                                                                           Toluene                 K
                      CH3           Al2O3 _ Pt
                                                                        + 3H2
                                         ْ
                                     550 C
                                                           Benzene

                                                                                                                   

                                                                                                                           

                                                            - ٤٩ -
       ‫א‬‫א‬                               ١٤٠                                        ‫א‬
  ‫א‬‫א‬                          ‫א‬‫א‬                         ‫א‬



                                                                W‫א‬‫א‬٣J ٧
‫א‬‫א‬‫א‬،‫א‬‫א‬ 
                 K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬


                                                      W‫א‬‫א‬‫א‬ .١
‫א‬‫א‬‫א‬ ‫א‬‫א‬
                                                                    W‫א‬


                                                                        WHalogenation‫א‬ K
 
‫א‬،‫א‬
‫א‬‫א‬،‫א‬‫א‬E‫א‬‫א‬‫א‬F‫א‬
،E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬،
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬K‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
                                  
‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                         K‫א‬
                                           CH2Cl                     CHCl2                 CCl3
                               CI2                    Cl2                     Cl2
                                /ً‫ﺿﻮ‬                  / ً ‫ﺿﻮ‬                  / ً ‫ﺿﻮ‬
              CH3
                                       Benzoyl                   Benzoal               Benzotrichoride
                                       choride                   choride
                                                   CH3                         CH3
                              Cl2/FeCl3
                                                           CI
          Toluene
                                                                      +

                                                                               Cl
                                          o-chlorotoluene                 p-chlorotoluene
                                                        - ٥٠ -
    ‫א‬‫א‬                                  ١٤٠                                       ‫א‬
  ‫א‬‫א‬                          ‫א‬‫א‬                        ‫א‬



                                                                              W‫א‬‫א‬ K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
                                  
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K
                                                                                               
 ‫א‬‫א‬‫א‬‫א‬
                                                                                                 K
                                                        
                                       CH3                                 COOH
                                                  KMnO4 or
                                                   K2Cr2O7

                                                                    Benzoic acid
                       CH2CH2CH3                             COOH
                           CH3                                  COOH
                                 KMnO or
                                     4
                                                                                +    (CO2 + H2O)
                                       K2Cr2O7

                                                    Phthalic acid
                                         ( 1,2- benzenedicarboxylic acid)


                                                                              W‫א‬ .١
                                                                             W‫א‬ -‫أ‬
،‫א‬‫א‬‫א‬
EthylbenzeneK‫א‬،‫א‬‫א‬‫א‬
                                                                                           KCyclohexane 
                                  CH 2CH 3                                             CH 2CH 3
                                                        Ni,Pt or Pd
                                         + 3H 2
                                                                            Ethylcyclohexane
                   Ethylbenzene


                                                        - ٥١ -
        ‫א‬‫א‬                                 ١٤٠                                       ‫א‬
      ‫א‬‫א‬                         ‫א‬‫א‬                        ‫א‬



                                                                               W‫א‬‫א‬‫א‬‫א‬
    ‫א‬E‫א‬‫א‬‫א‬‫א‬F‫א‬
    ،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
    ‫א‬،‫א‬‫א‬‫א‬
                                                                             
    ‫א‬‫א‬‫א‬‫א‬،
    ،‫א‬‫א‬‫א‬‫א‬K‫א‬
    ،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
    ‫א‬‫א‬‫א‬‫א‬‫א‬
               W‫א‬‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬
                                                                 Alkylation E‫א‬–F J ١


                                                                                  CH3
                                                           AlCl3
                                         + CH3Cl                                         + HCl
                           

                                             AcylationE‫א‬–F                                J ٢


                                                                                     O
                                                 O                                   C _ CH 3
                                               _ C _ Cl AlCl 3
                                          + CH3
                           

                                                                  Halogenation‫א‬                          J ٣
                                                                                                                    
                                                                                    Br
                                                               FeBr3
                                                   + Br2
                                   

                                                           - ٥٢ -
    ‫א‬‫א‬                                 ١٤٠                                         ‫א‬
  ‫א‬‫א‬                         ‫א‬‫א‬                          ‫א‬



                                                                    Nitroation‫א‬                        J ٤

                                                                                    NO2
                                                      H2SO4(conc.)
                                        + HNO3
                        
                                                                                ‫א‬                      J ٥
                                                       SO3H                                  Sulfonation
                              SO3
               + H2SO4                                                                                                

                                                                                                                  


                                                     W‫א‬‫א‬‫א‬٣J ٨
                                             
،‫א‬‫א‬‫א‬‫א‬‫א‬
                                                              
‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
AnisoleK‫א‬‫א‬،
K nitroanizole ‫א‬‫א‬‫א‬‫א‬
                                          K‫א‬‫א‬‫א‬
                            OCH3                         OCH3                   OCH3
                                      HNO3                  NO2
                                      H2SO4                               +

                                                                          NO2
‫א‬‫א‬
‫א‬‫א‬–‫א‬
                                                                                                   K‫א‬
                                       NO2                           NO2
                                               HNO 3
                                               H2SO4
                                                                             NO2



                                                       - ٥٣ -
   ‫א‬‫א‬                               ١٤٠                                  ‫א‬
  ‫א‬‫א‬                      ‫א‬‫א‬                   ‫א‬



                                                           
=O،R+F‫א‬‫א‬‫א‬‫א‬‫א‬
                                                      
‫א‬‫א‬‫א‬‫ א‬‫א‬EH+،Br+،NO2+،CH3C+
‫א‬‫א‬‫א‬‫א‬،‫א‬
 
‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                                         W‫א‬
 ‫א‬–‫א‬ .١
                           W‫א‬‫א‬‫א‬‫א‬
                                        -NH2(-NHR,-NR2) ,-OH >-OR,-NHCOCH3 > -C6H5 ,-R
                                                                 K‫א‬ERF
   K‫א‬‫א‬–‫א‬ .٢
                                       E-F,-Cl, - Br )

 W‫א‬‫א‬K‫א‬ .٣
                               K-NO2, -N+(R)3,-C=N,COOH( -COOR ),-SO3H,-CHO,-COR

                                                                                                       
                W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
  
‫א‬،‫א‬
                                                    K‫א‬‫א‬‫א‬




                                                    - ٥٤ -
   ‫א‬‫א‬                               ١٤٠                                   ‫א‬
  ‫א‬‫א‬                      ‫א‬‫א‬                    ‫א‬



                                          NO2                     NO2
                             HNO3                 Br2,Fe
                             H2SO4
                                                                        Br
                                                      m-bromonitobenzene
                                           Br                 Br                        Br
                                                                   NO2
                             Br2,Fe                HNO3
                                                                       +
                                                   H2SO4

                                                                                        NO2
                                                                 o-bromonitro  p-bromonitro
                                                                benzene (38%) benzene (62%)


                                                             W‫א‬‫א‬‫א‬٣J ٩
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                     
‫א‬K‫א‬
‫א‬K‫א‬،‫א‬‫א‬،EF
‫א‬‫א‬KE‫א‬F‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬،
                        K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                                                                         
                                                                                                         
                                                                                                         
                                                                                                         
                                                                                                         

                                                   
                                                   
                                                   
                                                       - ٥٥ -
  ‫א‬‫א‬                                      ١٤٠                                      ‫א‬
 ‫א‬‫א‬                             ‫א‬‫א‬                       ‫א‬



                                            
                                                                              W‫א‬‫א‬‫א‬W١
                                                                                                                  

                          CH = CH      2                         COOH                          CH3
                              Br                                                                        NO2
        a)                                     b)                                   c)
                                                                        CH3


                             CH3                                                                 COOH
                                                                                                     CI
        d)                                                                          e)
                      I            I                                                             NO 2

                                                                                                                  
                                                     W‫א‬‫א‬‫א‬‫א‬‫א‬W٢
    a) 1,3,5-trichloro benzen                                                b) m-bromotoluene
    c) p-bromoniro benzene                                                   d) lsopropyl benzene

    e) 4-bromo-2,3-dinitrotoluene                                            f) m-chloro benzoic acid

                                                                                                                  
                                    W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬W٣
                                                                                                                  
              CH(CH 3)2
                                           -
                             KMnO 4 / OH

                                                 
                      CH 3
                             Br 2 /hv




                                                          - ٥٦ -
      ‫א‬‫א‬                               ١٤٠                  ‫א‬
     ‫א‬‫א‬                      ‫א‬‫א‬   ‫א‬


                          NO 2
                                   Br 2
                                  FeBr 3
                  OC 2H5
                                              AICI 3
                           + CH 3CH 2CI

                  CI
                                        O
                                            AICI 3
                          + CH 3 C - CI

                  CH 3
                             H 2O 3
                             HNO 3


                                                   AICI 3
                          + CH 3 CHCI CH 3

                  CN
                                 Br 2
                            FeBr 3











                                                       - ٥٧ -
  ‫א‬‫א‬                                 ١٤٠                                               ‫א‬
 ‫א‬‫א‬                        ‫א‬‫א‬                               ‫א‬



                                    ٣J ٨
                                                                                                                      W١
                                                                                             O-Bromostyrene J ‫א‬
                                                                                         3,5- Diiodo tolueneJ 

                                                                                                                            
                                                                                                                    W٢
                                                                 CH3



                                                                       Br2
                                                                 CH (CH 3)2



                                                                               
                                                                                                                      W٣
                      CH(CH 3)2                            COOH
                                      -
                          KMnO 4/OH


               NO2                          NO 2
                            Br 2
                          FeBr 3
                                                     Br
               CH3                          CH3                    CH3
                                                    NO2
                          HNO2
                                                       +
                          H2SO4
                                                                   NO2
                                                                              CH (CH 3) 2
                                                   AICI 3
                      + CH 3 CHCI CH 3

                                                                                                       


                                                     - ٥٨ -
                                              ‫א‬‫א‬‫א‬
                                           ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                               ‫א‬‫א‬‫א‬‫א‬




                     ‫א‬‫א‬
                        ‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬




٤
   ‫א‬‫א‬‫א‬                                ١٤٠                                    ‫א‬
  ‫א‬‫א‬‫א‬                        ‫א‬‫א‬                     ‫א‬



                                                                                                    W‫א‬‫א‬
                                                                                      
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                             K‫א‬‫א‬‫א‬


                                                                                         W‫א‬‫א‬
                                                     W‫א‬‫א‬‫א‬
                                                               K‫א‬‫א‬‫א‬ .١
                            K‫א‬‫א‬‫א‬‫א‬‫א‬ .٢
                           K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫٣. א‬


                                                                                  W‫א‬‫א‬‫א‬
                                                       K٪٨٠‫א‬‫א‬‫א‬


                                                                                     W‫א‬‫א‬
                                                                                                 K


                                                                                  W‫א‬‫א‬
                                                     KOverhead Projector .١
                                                                  K‫א‬‫א‬ .٢
                                                                                           K .٣


                                                                                        W‫א‬‫א‬
                                                                         K‫א‬‫א‬‫א‬‫א‬




                                                     - ٥٩ -
    ‫א‬‫א‬‫א‬                                ١٤٠                                     ‫א‬
  ‫א‬‫א‬‫א‬                         ‫א‬‫א‬                      ‫א‬



                                                                           1J 4
             
،‫א‬‫א‬‫א‬‫א‬
                                                                                         
R،R - X‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬،X،
                             K‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬


                                                                 ‫א‬‫א‬‫א‬2J 4
                                                                                       
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                  
‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
       
K‫א‬‫א‬‫א‬‫א‬W‫א‬‫א‬
‫א‬F‫א‬Alkyl‫א‬‫א‬‫א‬
                                                                                  
‫א‬‫א‬EF‫א‬IUPAC‫א‬‫א‬،E
                                                                               W‫א‬‫א‬
                                                                                                      
                              CH3Cl                   CH3CH2CH2Br
                                                                                        1˚ halides
             (Methyl chloride)         (n – propyl bromide)
                                                                                      ‫א‬
             Chloromethane              1 - Bromopropane

                                                                                                             
                                                       CI
                  I
        CH3 - CH - CH3                                                                     2ºhalides
       EIsopropyl iodide)                                                                ‫א‬
                                         (Cyclopentyl chloride)
         2- Iodopropane
                                                         Chlorocyclopentane
                           CH3                                  CH3
    CH3 - CH2 - CH2 - C - CH = CH2                     CH3 - C - CH3                       3º halides
                                                                                          ‫א‬
                        Br                       Br
             3-Bromo-3-methyl-1-hexene (tert-Butyl bromide)
                                                      - ٦٠ -
    ‫א‬‫א‬‫א‬                                   ١٤٠                                        ‫א‬
  ‫א‬‫א‬‫א‬                            ‫א‬‫א‬                         ‫א‬



                                     W‫א‬‫א‬‫א‬‫א‬


                                 _               CH2 = CH
                         CH2 = CH CH2
                                                                                       CH2X
                                     X                        X
                           Allylhalide            Vinylhalide               Benzylhalide
                                                                                                                   
                   W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                                   
                     CCl4                            CHCl3                           CH2Cl2
             (Carbontetrachloride)                (Chloroform)                 (Methylene chloride)
              Tetrachloromethane                Trichloromethane                Dichloromethane


                                                                                         Br
                        CHBr3                            CHI3
                                                                                CH3 - C - CH2CH3

                      (Bromofoem)                    (Iodoform)                          Br
                                                                                2,2-Dibromobutane



                                                                                                                   


                                                                         ‫א‬‫א‬‫א‬3J 4
                                                                   
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                            
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬،‫א‬‫א‬
‫א‬F‫א‬‫א‬‫א‬K‫א‬
          K‫א‬E‫א‬‫א‬




                                                         - ٦١ -
    ‫א‬‫א‬‫א‬                                ١٤٠                                       ‫א‬
  ‫א‬‫א‬‫א‬                         ‫א‬‫א‬                     ‫א‬



                                                        ‫א‬‫א‬‫א‬3J 4
                                                                 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                 W


                       E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫١. א‬
            
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                          K‫א‬‫א‬‫א‬

                                            Cl2
                           CH3CH3                          CH3CH2CI + HCI + ...
                                         UV or heat
                                        ‫ﺿﻮ او ﺣﺮارة‬


                                                Br2
                      CH3 - CH = CH2                            CH2 - CH = CH2 + HBr
                                              UV or
                                                                 Br




                                         ‫א‬‫א‬‫א‬‫א‬ .٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                          W‫א‬‫א‬
                                                                   HCl
                                   CH3 - CH = CH2                              CH3 - CH - CH3
                                                                   CCl4
                                                                                     Cl
‫א‬‫א‬
                                                                                                W‫א‬‫א‬
                                                                   HBr
                                      CH3-CH = CH2               R-O-O-R        CH3CH2CH2
                                                                                          Br
                                                                                                     


                                                      - ٦٢ -
      ‫א‬‫א‬‫א‬                                 ١٤٠                                      ‫א‬
    ‫א‬‫א‬‫א‬                          ‫א‬‫א‬                       ‫א‬



 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                   HCl                             HCl
                                   CH CH                        CH2 = CH                  CH3CHCl2
                                         CCl4                                      CCl4
                                                                            Cl




                                E‫א‬‫א‬F‫א‬‫א‬‫א‬‫٣. א‬
                   
  ‫א‬HX‫א‬‫א‬‫א‬ ‫א‬‫א‬
                W‫א‬EPCl5 , PCl3 , PBr3F‫א‬‫א‬SOCl2‫א‬

                                                                                                                 
                                                                    HCl
                               CH3(CH2)5 CH2OH                                    CH3(CH2)5 CH2 +H2O
                                                                ZnCl2 / 150ْ
                                                                                             Cl
                                                                   NR 3
                               CH3CH2OH + SOCl 2                                 CH3CH2Cl + SO 2 + HCl


                                CH3CH2OH +PBr3                                   CH3CH2Br + P (OH)3
                                                                                                                 


                                                                             ‫א‬‫א‬5J 4
                                                                                     
  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬KE‫א‬F‫א‬‫א‬
  KE‫א‬F‫א‬
                                                                  KKKK‫א‬‫א‬


                     Nucleophilic substitution reactions‫א‬‫א‬‫א‬ K١
                              
   ‫א‬‫א‬‫א‬‫א‬
  E‫א‬‫א‬‫א‬F‫א‬‫א‬
                                                         - ٦٣ -
      ‫א‬‫א‬‫א‬                                ١٤٠                                      ‫א‬
    ‫א‬‫א‬‫א‬                         ‫א‬‫א‬                       ‫א‬



                             
  ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
                              W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬


                                      R3Cδ+χδ-                        R3C-Nu + χ –

                                             W‫א‬‫א‬‫א‬‫א‬
                                                     O
              -         -                                         -        -
             SR , SH , CH3NH2 , NH3 , - O - C - R , OR ,OH
             ..                               -          -
             N (CH3) 3 , HN (CH3)2 ,      CN ,R - C = C
                                                                                                                
  ‫א‬،‫א‬‫א‬‫א‬‫א‬
                                                                       
                                 W‫א‬ ‫א‬
                                                                                                                
                                                      KOH
                                   CH3CH2CH2Br                        CH3CH2CH2OH
                                                      H2 O




                                          Elemination reactionsEEFE‫א‬‫א‬F‫א‬ K٢

                                                                            
   ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬E‫א‬‫א‬‫א‬‫א‬F‫א‬

                                                        -  +

                            CH3CH  _ CH KOH (Or) CH3CH2O Na CH - CH = CH
                                       3                      3          2
                                         EtOH /
                                Br




                                                         - ٦٤ -
   ‫א‬‫א‬‫א‬                                ١٤٠                                      ‫א‬
  ‫א‬‫א‬‫א‬                        ‫א‬‫א‬                       ‫א‬




                                                -4‫א‬‫א‬                  K٣
                                          Grignard formation K

                                                            
   K‫א‬‫א‬‫א‬‫א‬‫א‬ 

                                                       ether
                        CH3CH2CH2Br + Mg                          CH3CH2CH2MgBr

 ‫א‬ ‫א‬          
      K،‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                         ‫א‬ K
                                                                W‫א‬‫א‬

                                                                         - +
                      CH3CH2CH2Br + 2Li                         CH3CH2CH2 Li + LiBr

     K‫א‬‫א‬‫א‬‫א‬‫א‬


                                                          ‫א‬‫א‬‫א‬٤J ٦
‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                      KD.D.T.‫א‬
                                                        H

                                     Cl                C                   Cl
                                                       CCl 3

                                                   D.D.T
                                                                                                             
‫א‬‫א‬‫א‬–[CF2–CF2]nTeflonW‫א‬
‫א‬–[H2–CCl2]n–‫א‬‫א‬‫א‬‫א‬‫א‬
K‫א‬‫א‬‫א‬‫א‬–[CH2 – CHCl2-]n–PVC K‫א‬

                                                     - ٦٥ -
   ‫א‬‫א‬‫א‬                                     ١٤٠                                    ‫א‬
  ‫א‬‫א‬‫א‬                             ‫א‬‫א‬                     ‫א‬



CCl3FCCl2F2‫א‬CF3CHClBr‫א‬HCX3haloform‫א‬
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
              Antifungus‫א‬Antibiotics‫א‬‫א‬‫א‬
                                                                                                                     

                                            ٤J ٧
                                        EIUPAC F‫א‬‫א‬‫א‬‫א‬W١
                                                                                                                 
                           Br
                                                                           CH3CH_ CH _ CH3
                                                        E                                           E
                                                                             Br CH3
                     
                                  NO2

                                  _                                           _   _
                                CH CH3                E                 CH 3 CH2 CH=CH 2           E
                                Cl                                                   Cl
               
                                                        
                                                                        
                                                                           CH2 = CH CH2Cl            E
                                                                                                                     
                                                                   E3◦ 2◦1◦F‫א‬‫א‬‫א‬W٢
                                                                                                                     
                                                                                         Br
                     CH3                           Cl CH3
        CH3 C CH3                E                                         E                             E
           Cl                                                                    
                                                                                                                     
                                                          K‫א‬‫א‬‫א‬‫א‬W٣
                                                                                                                     
                   CH3
                                HCl                                                                   E
           CH3CHOH ZnCl
                        2

                                     HBr
           CH 3                                                                                      E


                                                             - ٦٦ -
  ‫א‬‫א‬‫א‬                                       ١٤٠                               ‫א‬
 ‫א‬‫א‬‫א‬                               ‫א‬‫א‬                ‫א‬


                CH3
                              Br2                                                                E
          CH3CHCH3            hv
                                          Cl2
                       CH2CH3             hv


                                     SOCl2
                       OH                                                                         E

                                  + -
                           _ CH Na O CH2CH3
          CH3CH2CH                  3 CH3CH2OH                                                   E
                 Br
              Br
                                                KOH
          CH3 C CH2
                                                EtOH
                     CH3
                                    NH2CH3                                                        E
          CH 3CH 2CH 2Cl
                                                       -    +
                                           CH3C      C Na
                       CH 2CH2Br                                                                 E

                               KOH
          CH 3CH _ CH 3                                                                           E
                               EtOH /
                Br
                                             ether                                                E
          CH 3CH 2CH 2Br + Mg
                                                                                                             
                                                            W‫א‬‫א‬‫א‬‫א‬W٤
                                                                                                                 
                                      -
                                 OH                                                              E١
          CH 3CHBrCH 3 ethanol
                                      -
                       OH                                                                        E٢
          CH 3CHBrCH 3 H2O
                                -
                             CN                                                                  E٣
          (CH 3)3CBr
                           ethanol
                             H2 O                                                                E٤
          (CH 3)3CBr
                                                                                                             
                                                                                                             
                                                                                                             
                                                                                                             

                                                           - ٦٧ -
  ‫א‬‫א‬‫א‬                                   ١٤٠                                     ‫א‬
 ‫א‬‫א‬‫א‬                           ‫א‬‫א‬                      ‫א‬


                                                                                                                  

                                         ٤J ٧
                                                                                                                  

                                                                                                           W١
                                                                                    2-Bromo-3-methyl butane–
                                                                               1-Bromo-2-Nitro cyclohexaneJ 
                                                                                         1-chloro-1-buteneJ 

                                                                                                              
                                                                                                            W٢

                      3◦              E        2◦           E      1◦          E
                                                                                                                  

                                                                                                           W٣
                    CH3                  CH3
                             HCl
                                      CH3CHCl + H2O
                                                                                                    E
          CH3CHOH ZnCl
                       2

                CH3                           CH3
                             Br2
          CH3CHCH3           hv       CH3 C CH3                                                    E
                                          Br
                                   NH2CH3                                                           E
          CH3CH2CH2Cl                         CH3CH2CH2NHCH 3
                      KOH
          CH CH_ CH
               3           3 EtOH /          CH 3CH=CH 2 + HBr                                      E
                Br
                                                                                                                  

                                                                                                           W٤
                                                                                           ‫א‬‫א‬J ١
                                                                                         ‫א‬‫א‬J ٢
                                                                                         ‫א‬‫א‬J ٤
                                                                                                                  
                                                                                                              




                                                       - ٦٨ -
                                            ‫א‬‫א‬‫א‬
                                         ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                             ‫א‬‫א‬‫א‬‫א‬




                    ‫ א‬‫א‬
                             ‫א‬
                     ‫א‬‫א‬
‫א‬‫א‬




٥
    ‫א‬‫א‬                                  ١٤٠                                      ‫א‬
   ‫א‬‫א‬                       ‫א‬‫א‬                      ‫א‬



                                                                                      W‫א‬‫א‬
                                                                   
‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬
                                                                                     K‫א‬‫א‬‫א‬
                                                                                                           
                                                                                     W‫א‬‫א‬
                                              W‫א‬‫א‬‫א‬
                                                                  K‫א‬‫א‬ .١
                               K‫א‬‫א‬‫א‬‫א‬ .٢
                       K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ .٣
                                                                                                   
                                                                              W‫א‬‫א‬‫א‬
                                                 K٪80‫א‬‫א‬‫א‬
                                                                          KW‫א‬‫א‬
                                                                                                           
                                                                                 W‫א‬‫א‬
                                                      KOverhead Projector .١
                                                   K‫א‬‫א‬‫א‬ .٢
                                                                                           K .٣
                                                                                                       
                                                                                        W‫א‬‫א‬
                                                                        K‫א‬‫א‬‫א‬‫א‬




                                                    - ٦٩ -
     ‫א‬‫א‬                                     ١٤٠                                    ‫א‬
   ‫א‬‫א‬                          ‫א‬‫א‬                     ‫א‬



                                                                                      W5J 1
J OH‫א‬‫א‬ 
‫א‬‫א‬‫א‬،ArOH‫א‬‫א‬،ROH‫א‬‫א‬‫א‬
               
 Ar ‫א‬R،ArR‫א‬‫א‬
،SP3‫א‬‫א‬‫א‬،
KSP2‫א‬‫א‬
‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬
              
‫א‬‫א‬‫א‬K‫א‬
‫א‬K‫א‬‫א‬
                            K‫א‬


                                                                  W‫א‬5J 2
           
‫א‬‫א‬‫א‬‫א‬‫א‬
   W‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
                                                                                                             
                                                          
                           O                                O
           Tertiary 3                    Secondary 2                          Primary 1O

                       H                           R                              H
               R       C       OH         R        C       OH                R    C    OH
                       R                           R                              H

           ‫א‬ ‫א‬   ‫א‬ ‫א‬   ‫א‬ ‫א‬ 
            J OH   J OH   J OH 
           ‫א‬                                    
                             K‫א‬                      KR‫א‬
                       K‫א‬




                                                       - ٧٠ -
      ‫א‬‫א‬                                      ١٤٠                                            ‫א‬
     ‫א‬‫א‬                           ‫א‬‫א‬                            ‫א‬



                                                                             W‫א‬5J 3
‫א‬KIUPAC‫א‬‫א‬‫א‬‫א‬،
                                                         K‫א‬‫א‬‫א‬‫א‬


                                                                                    W‫א‬‫ א‬K١
                   W‫א‬‫א‬‫א‬‫א‬
                                                                                                                 
             CH3 OH                                 CH3CH2OH                                 CH2=CH-CH2OH
            Methyl alcohl                           Ethyl alcohol                             Allyl alcohol

                                    CH3
                                                                             CH3     CH        CH3
                             CH3   c      CH3
                                                                                      OH
                                   OH


                             Isopropyl alcohol                               Tert-Butyl alcohol


                                       OH                                             CH2OH




                         Cyclopentyl alcohol                                  Benzyl alcohol
                                                                                                                       


                                                                WE‫א‬FW‫א‬‫ א‬K٢
J   OH‫א‬‫א‬                  K١
EeF‫א‬‫א‬‫א‬‫א‬‫א‬
                                                 
                                                                                         WKJ    ol
                               CH3OH
                                                                              CH3CH2OH




                                                          - ٧١ -
    ‫א‬‫א‬                                               ١٤٠                                           ‫א‬
   ‫א‬‫א‬                                    ‫א‬‫א‬                           ‫א‬


                                     Ethanol                                                 Methanol
-OH‫א‬‫א‬‫א‬‫א‬                                 K٢
‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
           W‫א‬‫א‬‫א‬E١F‫א‬‫א‬‫א‬
                                                                                                                     
                                                                            CH3CH2CH2CH                   CH3
                              CH3CH2CH2OH
                                                                                             OH
                                  1-Propanol                                            2-Pentanol
                                                                                            C 2H 5
                                             OH
                                                                                    CH3CH2CHCH2CHCH3


                                                                                                     OH
                                Cyclohexanol                                         4-Ethyl-2-hexanol

                                                                 CH2CH2Br


                                               CH3CH2CH2CHCH2 OH

                                         2-(2-Bromoethyl)-1-Pentanol

                                                                                                                     
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬                                       K٣
‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
                              
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                                   K‫א‬
                                                                                                CH2CH3
                       CH2      CH      CH        CH       CH3
                                                                                    CH3CH       C     CH2
                                        OH        CH3
                                                                                        OH
                             4-Methyl-1-Penten-3-ol                                 3-Ethyl-3-buten-2-ol
                                                                                               OH
                       CH         C          CH         CH3

                                             OH
                                                                                               CH3
                                 3-Butyn-2-ol                                4-Methyl-2-cyclohexenol

                                                                 - ٧٢ -
    ‫א‬‫א‬                                ١٤٠                                   ‫א‬
   ‫א‬‫א‬                     ‫א‬‫א‬                  ‫א‬



             
 -ol ‫א‬tetra,tri ,di‫א‬‫א‬‫א‬        K٤
                                                    KK‫א‬
                                                                                                     
                                                                                                     
                                             CH2        CH2           CH2     CH     CH2


                                              OH        OH            OH      OH     OH

                                1,2-Ethanediol             1,2,3-Propantriol

                                Ethylene glycol           Glycerol or Glycerene



                                                                                   W‫א‬
  
  ‫א‬  ‫א‬     ‫א‬   
،‫א‬ -OH ،
،‫א‬‫א‬‫א‬
                                                                                 W‫א‬‫א‬
                                                 OH                           OH
                            OH




                                                            Br                NH2
                        Phenol             m-Bromophenol                p-Aminophenol
                                                                              OH
                       OH

                                 COOH


                                                                              OH
            o-Hydroxybenzoic acid (
                Salicylic acid)
                                                                       Hydroquinone


                                                                                                     




                                                   - ٧٣ -
     ‫א‬‫א‬                                         ١٤٠                                          ‫א‬
   ‫א‬‫א‬                               ‫א‬‫א‬                          ‫א‬




                                                  W‫א‬‫א‬‫א‬‫א‬5J 4
‫א‬‫א‬،‫א‬‫א‬‫א‬
‫א‬ ‫א‬  ‫א‬ ‫א‬     ‫א‬   
‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬
                         K‫א‬‫א‬،EF‫א‬‫א‬
                                                        R                                        Ar
                                                                                   Ar
                                               O                                           O
                             O                                                 O
                                                                                                 H
                        R              H                H
                                                                                    H


                 
                                                                                                  ‫א‬
‫א‬‫א‬‫א‬‫א‬
                                                                                    K‫א‬‫א‬‫א‬
                        Ethanol                          Propane
                 L٤٦                              °٧٨                           ‫א‬‫א‬
                       L٤٤                         °٤٢                           ‫א‬
                      
،‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
                                                                       
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                                                                K‫א‬
                                                                     H              R
                                               o              o                o
                                           R        H
                                                                     H               H



                                   
                                                    ‫א‬
                                                            - ٧٤ -
     ‫א‬‫א‬                                   ١٤٠                                            ‫א‬
   ‫א‬‫א‬                         ‫א‬‫א‬                            ‫א‬



                                                                              W‫א‬‫א‬5J 5
                                                                          W‫א‬            K 
،‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                     K‫א‬
                                                                                      H
                                                                    +
                                                                   H
                              CH3CH          CH2    + H2 O                  CH3       CH      CH3
                                     Propene                                       2-Propanol
                                            ‫א‬                  
‫א‬،EthanolMethanol ‫א‬‫א‬
                                                                                        W


                  water gas‫א‬‫א‬‫א‬‫א‬W‫א‬ K
                                              KE‫א‬‫א‬ F
                                                           O
                                                      1300 C
                                     C +H2O                      CO + H2

‫א‬‫א‬‫א‬Water gas
                                                     K300 atm300c‫א‬
                                                                                
                                                Zn + Cr 2 O3 as Cat.
                         CO + H 2 + H2                                            CH3OH
                         Water gas


                                                              WNatural gas‫א‬‫א‬ K
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                  K900 Co
                                                  Ni as Cat.
                         CH4 + H2O                                           CO + 3H 2O
   K‫א‬‫א‬‫א‬Synthesis‫א‬‫א‬‫א‬
                                 ZnO + Cr 2 O3 as Cat.
                     CO + H 2O           O                         CH3OH
                                     300C , 300 atm.

                                                                                                                   

                                                      - ٧٥ -
  ‫א‬‫א‬                                    ١٤٠                                           ‫א‬
 ‫א‬‫א‬                         ‫א‬‫א‬                           ‫א‬



                                                      W‫א‬‫א‬
                       ‫א‬                               K 
                                    : Ethyl hydrogen sulphate٨٠Co‫א‬
             CH2           CH2 + H2SO4                  CH3            CH2      O      SO2          OH

                                    K‫א‬
                     CH3     CH2       O       SO2           OH   +    H2O          CH3 CH2 OH + H2SO4


                ‫א‬ ‫א‬ ‫א‬   ‫א‬ ‫א‬                       K
                  Phosphoric F‫א‬‫א‬
               Co‫א‬E‫א‬‫א‬acid on silca
                                                        K70 atm٣٠٠
                                                                        W‫א‬             K 
‫א‬‫א‬‫א‬‫א‬
                        K‫א‬‫א‬‫א‬‫א‬
                     SO3H                        - +                                      OH
                                                 ONa

                             NaOH
                                                               HCl



               Benzene sulfonic acid            Sodium phenoxide                         Phenol


                                                        W‫א‬‫א‬
                      
     ،Propene‫א‬‫א‬‫א‬‫א‬، Cumene‫א‬ E١
     AlCl3‫א‬‫א‬‫א‬‫א‬
                                                                           K‫א‬‫א‬
                               K‫א‬‫א‬
                                                                                    CH         CH3

                             + CH3       CH         CH2
                                                                                    CH3

                                                                               Cumene
                                                    - ٧٦ -
    ‫א‬‫א‬                                                ١٤٠                                              ‫א‬
   ‫א‬‫א‬                                  ‫א‬‫א‬                                 ‫א‬



                                      
‫א‬‫א‬Hydroperoxide‫א‬‫א‬‫א‬‫א‬
                                                                   K‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                        CH3
                                                                                              OH

                       CH        CH3                                    C     CH3       +
                                                                                       H
                                        + O2                                                         + ( CH3 )2 C      O
                       CH3                                              O     OH
                                                                                            Phenol         Acetone

                                                                                                                             
                               K‫א‬‫א‬‫א‬‫א‬
                                                                    W‫א‬‫א‬ E٢
                                                                                     - +
                                                 Cl                                 O Na
                        Cl2                                                                   +                      OH
                                                        NaOH
                                                                                             H
                             o                               o
                        40 C                            330 C

             Benzene              Chlorobezene                    Sodium phenoxide                     Phenol



                                                                            W‫א‬‫א‬5J 6
                                                          W‫א‬‫א‬

                                                       W‫א‬‫א‬‫א‬‫א‬‫א‬‫١- א‬
‫א‬ ،‫א‬‫א‬‫א‬‫א‬
                              K‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                             H2SO4
                                  2CH3CH2OH                         O
                                                                            (CH3CH2) 2 + H2O
                                                             140 C

                                       Ethanol                              Diethyl ether

                                                 H2SO4
                            CH3CH2OH                     O
                                                                  CH2           CH2     + H2O
                                                  180 C
                                                                        Ethylene

                              K‫א‬‫א‬‫א‬‫א‬‫א‬




                                                                 - ٧٧ -
   ‫א‬‫א‬                                     ١٤٠                                             ‫א‬
 ‫א‬‫א‬                          ‫א‬‫א‬                             ‫א‬



                                                                                          W Oxidation‫א‬
 ،‫א‬‫א‬‫א‬ E1F‫א‬‫א‬
                                                         
        ‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬
                                             W‫א‬‫א‬،‫א‬
                                                                         Cu/
                                              CH3CH2OH            CrO3 or Pyridine
                                                                                            CH3CHO
                                                              O
                                                Ethanol (1)                               Acetaldehyde
                                                                                                    3+
                                                            H2Cr2O7
                               CH3CH2OH                                         CH3COOH + Cr
                                                                                  Acetic acid
                                         OH                                                 O

                                                           H2Cr2O7
                                CH3CHCH3                                       CH3          C     CH3
                                                       or Cu /
                                               o
                                     Alcohol ( 2 )                                       Ketone


                     O                                                               
                            Oxid.Agent
              CH3-C-CH3                               
                     CH3


                                                                                  W‫א‬‫٢- א‬
‫א‬‫א‬‫א‬‫א‬
        ،‫א‬‫א‬‫א‬‫א‬
                                                                                                   K‫א‬
                                                                - +
                           CH3 OH      + Na                CH3 O Na + 1 H2
                                                                      2
                           Methanol                      Sodium Methoxide

                                                                  - +
                              OH                                  O Na



                                        + Na                             + 1 H2
                                                                           2


                            Phenol




                                                     - ٧٨ -
 ‫א‬‫א‬                                           ١٤٠                                   ‫א‬
‫א‬‫א‬                            ‫א‬‫א‬                       ‫א‬




                                                                                    W‫א‬‫א‬ -٣
                                         
     K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                          
                                                                        K‫א‬H+‫א‬
                                                                        O
                                             +
                                             H
         (Ar)R       OH + RCOOH                          (Ar)RO         C     R + H2 O
         Alcohol or Phenol                                           Ester
                                                 +
                                                 H
         CH3COOH + CH3CH2OH                                CH3COOCH2CH3 + H2O
          Acetic acid        Ethyl alcohol                         Ethyl acetate




                                                     




                                                          - ٧٩ -
    ‫א‬‫א‬                                           ١٤٠                                              ‫א‬
‫א‬‫א‬                                   ‫א‬‫א‬                              ‫א‬



                                             E‫א‬‫א‬F
                               
 WE3FE2FE1F‫א‬‫א‬‫א‬‫א‬                                     E١
                                        CH3 CH2 CH2 OH                                                     CH2CH3            (A
                                                                              (B
                                                                                          CH3        CH2   C         OH

                                                                                                           CH2CH3
                                                                                     
                              Br             (D                     CH3                         (C

      CH3           CH        CH2                     H2 C          C           CH2 OH


                    OH
                                                                                    W‫א‬‫א‬             E٢
                         (A                                (B                   OH              (c                           (D
              OH                                                                                                 OH
                                            CH2OH                     CH3                CH 3



     Br                            OH
              NH2                                                               CH3
                                           OH

                                                                                           W‫א‬‫א‬         E٣
                                                                                                           (A

               CH3       CH        CH2CH3                    CH3          C        CH2CH3

                         OH                                               O
          
                                                                                                           (B
                              O
                                                            +
                                                           H
               CH3 CH2 C OH             +   CH3OH
          
              CH3 CH2 CH2 OH                 Cu ,                     ?                                         (C
          
                                                            H2SO4                  ?                             (D
                          OH        +       K2Cr2O7


                                                                    OH

                                                                                                                (E

          
                                                             - ٨٠ -
 ‫א‬‫א‬                                      ١٤٠                                  ‫א‬
‫א‬‫א‬                           ‫א‬‫א‬                  ‫א‬



                                                           W‫א‬‫א‬‫א‬‫א‬       E٤
                    1) 2,4-Dimethyl-2-Octanol.
                    2) Cyclopentane-1,4-diol.

                    3) 2,2,2-Trichloroethanol.

                    4) 2-Butene-1,4-diol.

                    5) 3-Bromo-2-nonanol.

                    6) O- Bromophenol.

                    7) 2,4,6-Trichlorophenol

                    8) p-Hydroxybenzyl alcohol.


                                                                                                        
                                                                                                    
                                                                                                    
                                                                                                    
                                                                                                    
                                                                                                    
                                                                                                    
                                                                                                    
                                                                                                    
                                                                                                    




                                                     - ٨١ -
 ‫א‬‫א‬                                      ١٤٠                                            ‫א‬
‫א‬‫א‬                      ‫א‬‫א‬                                 ‫א‬




                                  E‫א‬‫א‬F
                                                                                           WE1F‫א‬‫א‬
                     K3o،                      1,1-Diethyl propanol             EA
                       . 2o،                         1-Bromo-2-propanol            (D
                                                                                           WE2F‫א‬‫א‬
                                                                    4-Amino-5-bromo phenol           EA
                                                                        2,4,6-Trimethyl phenol          EC
                                                                                           WE3F‫א‬‫א‬
                                                                 KMnO 4                               (A
                                                                  H2O
                                                    
                                                                          O
                                                                                                      (B
                                                         CH3 CH2 C O CH 3
                                                
                                                                          O
                                                           CH3 CH2 C H                                (C
                                            
                                                                                           WE4F‫א‬‫א‬
                                                       CH3
                                       CH3-CH2-CH2-CH2-C-CH2-CH-CH3                              (1
                                                                         CH3     OH


                                                                    
                                                                         CCl3-CH2-OH             (3
                                 CH3-CH2-CH2-CH2-CH2-CH2-CH-CH-CH3                               (5
                                                                               Br OH
                             
                                                                          OH
                                                                  Cl            Cl               (7


                                                                          Cl
                                                             
                                                                                                                  


                                                        - ٨٢ -
                                  ‫א‬‫א‬‫א‬
                               ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                   ‫א‬‫א‬‫א‬‫א‬




          ‫ א‬‫א‬
                   ‫א‬
                  ‫א‬‫א‬
‫א‬‫א‬




٦
     ‫א‬‫א‬                            ١٤٠                                      ‫א‬
         ‫א‬‫א‬                        ‫א‬‫א‬                      ‫א‬



                                                                                    W‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                          
                                                                                    W‫א‬‫א‬
                                               W‫א‬‫א‬‫א‬
                                                                               K‫א‬‫א‬ .١
                                              K‫א‬‫א‬‫א‬‫א‬ .٢
                                                                                                      
                                                                            W‫א‬‫א‬‫א‬
                                                  K٪80‫א‬‫א‬‫א‬
                                                                                                          
                                                                                  W‫א‬‫א‬
                                                                                            K
                                                                                                          
                                                                            W‫א‬‫א‬
                                               KOverhead Projector .١
                                                                                      K .٢
                                                                                                
                                                                                     W‫א‬‫א‬
                                                                     K‫א‬‫א‬‫א‬‫א‬
                                                                                                          




                                                 - ٨٣ -
   ‫א‬‫א‬                                          ١٤٠                                          ‫א‬
        ‫א‬‫א‬                                     ‫א‬‫א‬                          ‫א‬



                                                                          W6J 1
 R/RR-O-R/‫א‬‫א‬‫א‬‫א‬  
                                                    WK
                                             
‫א‬‫א‬‫א‬،R/R‫א‬‫א‬
                                                                           K‫א‬


                                                                W‫א‬‫א‬6J 2
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬،Ether
                                                                      
                                                                                                                 K‫א‬
                  CH3OCH2CH3                       CH3CH2OCH2CH3                            CH3OCH3
                                                          Ethyl ether                       Methyl ether
                     Ethyl methyl ether


                                          o       CH3                                   o
                           Methyl phenyl ether                                     Phenyl ether
                                  ( Anizole )
-O-R،IUPAC ‫א‬‫א‬‫א‬‫א‬
‫א‬،‫א‬REAlkoxy)‫א‬
                        W‫א‬‫א‬R(Aryloxy)
                                                                                CH3CH2CHCH3
                  Br                          o CH2CH3
                        p-Bromophenoxy ethane
                                                                                         oCH3
                                                                                2-Methoxy butane

                                                                o CH2 CH3

                                                  Ethoxy cyclohexane
‫א‬‫א‬‫א‬oxa‫א‬
            W‫א‬‫א‬‫א‬‫א‬ K‫א‬

                                                             - ٨٤ -
     ‫א‬‫א‬                                     ١٤٠                                     ‫א‬
         ‫א‬‫א‬                                 ‫א‬‫א‬                     ‫א‬



                             1         2     3 4             5     6   7         8    9
                             CH2       O     CH2 CH2         O     CH2 CH2            CH3
                                                                                 O
                             Cl

                                       1-Chloro-2,5,8 -trioxanonane
                                            W‫א‬‫א‬

                                                                                           O


                         o                             o                                  O
                   Oxlane                          Oxane                             1,4-Dioxane
                     or                            or                                     or
               Tetrahydrofuran               Tetrahydropyran                   1,4-Dioxa cyclohexane
                       ( THF )

                                   o
                                                                                       o
                             CH2           CH2
                                                                                 Oxetane
                          Oxiran e cepoxide
                                                                                      or
                                  or                                         Trimethylene oxide
                           Ethylene oxide
         

                                                                          W‫א‬‫א‬‫א‬‫א‬
                                                      
 ‫א‬‫א‬،‫א‬‫א‬
               
 K‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬،‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                      K‫א‬
 ‫א‬،‫א‬،‫א‬‫א‬‫א‬‫א‬        
                                                                               
 ‫א‬،‫א‬‫א‬،‫א‬‫א‬‫א‬ ‫א‬K‫א‬
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬




                                                          - ٨٥ -
   ‫א‬‫א‬                                  ١٤٠                                     ‫א‬
       ‫א‬‫א‬                              ‫א‬‫א‬                     ‫א‬



                                    R
                                            O          H
                                                               O           R
                                       R
                                                       H           O

                                                                           R
                                
                                                                                                           
 W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

                 ‫א‬   ‫א‬   ‫א‬‫א‬                 ‫א‬         ‫א‬

                            o78             46                    Ethanol      CH3CH2OH


             
                              o24J               46              Methylether          CH3OCH3


                          o42J               44                   Propane     CH3CH2CH3



                                                     W‫א‬‫א‬‫א‬6J 3
‫א‬‫א‬F‫א‬‫א‬‫א‬ 
                                                                           
،‫א‬‫א‬‫א‬E‫א‬‫א‬‫א‬
                                                                         K
‫א‬‫א‬‫א‬‫א‬‫א‬
                                        
‫א‬EPeroxide)‫א‬(‫א‬‫א‬‫א‬F
                                                                                           K
‫א‬‫א‬‫א‬‫א‬
،Fe+++‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬ FeSO4
                                                         
  W‫א‬‫א‬‫א‬‫א‬




                                                     - ٨٦ -
   ‫א‬‫א‬                                      ١٤٠                                              ‫א‬
        ‫א‬‫א‬                                 ‫א‬‫א‬                              ‫א‬



                                                                                                                        
                                                                     -
                                                   +++        SCN
                             Peroxide + Fe                                        Fe(SCN)3
                                                                                       
                      W‫א‬‫א‬‫א‬‫א‬‫א‬
         ‫א‬F‫א‬‫א‬ .١
                             KE‫א‬‫א‬
                                                    K‫א‬‫א‬‫٢. א‬
                          
                        K‫א‬‫א‬‫א‬‫א‬‫٣. א‬


                                                                                           W‫א‬‫א‬6J 4

                                                                          W‫א‬‫א‬‫א‬W
                                                             
         ‫א‬‫א‬‫א‬W‫א‬‫א‬‫א‬‫١. א‬
                                                               
         ‫א‬‫א‬‫א‬K‫א‬‫א‬
                                                                                               K‫א‬‫א‬
                                                                         H2SO4
                                                CH3CH2OH                                 CH3CH2OCH2CH3
                                                                            140
                                                                                             W .٢
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
F‫א‬‫א‬،Ealkoxide ion‫א‬F‫א‬
                   K‫א‬‫א‬‫א‬Ephenoxide ion‫א‬
                     - +
CH3      CH          O Na   + CH3CH2Br                   CH3         CH           O        CH2CH3

         CH3                                                          CH3

                                                                  Ethyl isopropyl ether




                                                         - ٨٧ -
       ‫א‬‫א‬                                 ١٤٠                                         ‫א‬
           ‫א‬‫א‬                             ‫א‬‫א‬                         ‫א‬



                                    - +
                                   O Na                                            O CH3


                                           + CH3Br


                                                                                Anizole


                                                                            W‫א‬‫א‬‫א‬W

                                                                   W‫א‬‫א‬‫א‬‫١. א‬
                                     K‫א‬‫א‬‫א‬‫א‬

                                             W‫א‬Diethyl ether .٢
    ‫א‬‫א‬‫א‬‫א‬
                                                                                 K‫א‬‫א‬


                                                                              W‫א‬‫א‬6J 5
             
    ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                            K‫א‬‫א‬‫א‬‫א‬،
                                                                   +
                                                                  H
                         CH3 CH 2 O CH 2 CH 3 + 2HI                           2CH3 CH 2-I + H 2O

                                                                              Iodoethane









                                                        - ٨٨ -
 ‫א‬‫א‬                                           ١٤٠                                            ‫א‬
     ‫א‬‫א‬                                       ‫א‬‫א‬                            ‫א‬



                                            E‫א‬‫א‬F

                                                                                            W‫א‬‫א‬ .١
                C6H5CH2                O       C3 H7                               CH3CH2CH2OCH2CH3E1
                                                       E4
           CH3 CH                  CH2 CH CH3          (5                            (CH3CH2CH2CH2)2OE2


                       CH3             O CH2CH3

                                                               CH3             O           CH CH3                 (3
                                                        (6

                                                                                           CH3
                                      O CH2 CH3



                                                                W‫א‬‫א‬‫א‬‫٢. א‬
         1) Diisopropyl ether.                                   2) Diallyl ether.
         3) tert-Butyl methyl ether.                             4) Benzyl ether.
         5) Phenyl ether.                                        6) 4-Ethoxy -2-Methylhexane.


                 W‫א‬‫א‬‫א‬‫א‬‫א‬‫٣. א‬
                                                         CH3


          (1)          +     (2)             CH3         C        O            CH2                           (1

                                                         CH3

                              O-
                           CH3O + (CH3)3CBr                                          (3)                      (2
                   
                                       -
                                       O
                           (CH3)C      O    + CH3I                                 (4)                        (3
                   

                                                                                                              
                                                        HI acid conc.
           (CH 3)2CHCH 2OC(CH 3)3                                                           (5)               (4
                                                        with



                                                             - ٨٩ -
 ‫א‬‫א‬                         ١٤٠                              ‫א‬
     ‫א‬‫א‬                   ‫א‬‫א‬                ‫א‬



                         K‫א؟‬‫א‬‫א‬ .٤
          CH3CH2CHCH2CH2CH3         (2            CH3CH2CH2CH2CH2CH2CH3      (1
                   OH
                                            CH3CH2CH2      O   CH2CH2CH3     (3
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         
                                                                                         

                                         - ٩٠ -
 ‫א‬‫א‬                              ١٤٠                                      ‫א‬
     ‫א‬‫א‬                          ‫א‬‫א‬                      ‫א‬



                                                                                                      
                            E‫א‬‫א‬F
                                                                                    WE1F‫א‬‫א‬
                          Dibutyl ether       (3                  Ethyl propyl ether        (1
                                                                  Isopropyl methyl ether    (5
                                                                                   WE2F‫א‬‫א‬
               CH 3 O C (CH 3)3       (2                (CH 3)2 CH O CH (CH 3)2            (1
                                               CH3-CH-CH 2-CH 2-CH-CH 3                    (6
                                                        CH3                O C2H5
                                                                                   WE3F‫א‬‫א‬
                                                                   (CH3)3 C O CH 3         (2
                                                                   (CH3)3 C O CH 3         (3
                                                                                                      
                                                                                                      




                                               - ٩١ -
                                                      ‫א‬‫א‬‫א‬
                                                   ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                                       ‫א‬‫א‬‫א‬‫א‬




                              ‫א‬‫א‬
                             ‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬




٧
   ‫א‬‫א‬                                     ١٤٠                                       ‫א‬
  ‫א‬‫א‬‫א‬                         ‫א‬‫א‬                       ‫א‬



                                                                                                           W‫א‬‫א‬
                                                                                                  
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                             K‫א‬‫א‬‫א‬‫א‬


                                                                                         W‫א‬‫א‬
                                                   W‫א‬‫א‬‫א‬
                                                              K‫א‬‫א‬‫א‬ .١
                                                        K‫א‬‫א‬‫א‬‫٢. א‬
                            K‫א‬‫א‬‫א‬‫א‬‫א‬ .٣


                                                                                  W‫א‬‫א‬‫א‬
                                                   K٪80‫א‬‫א‬‫א‬
                                                                                                                
                                                                                        W‫א‬‫א‬
                                                                                              K


                                                                                     W‫א‬‫א‬
                                                           KOverhead Projector  .١
                          K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ .٢


                                                                                          W‫א‬‫א‬
                                                                            K‫א‬‫א‬‫א‬‫א‬
                                                                                                                
                                                                                                                
                                                                                                                
                                                                                                                


                                                        - ٩٢ -
    ‫א‬‫א‬                                      ١٤٠                                      ‫א‬
   ‫א‬‫א‬‫א‬                         ‫א‬‫א‬                       ‫א‬



                                                 W7J 1
 ‫א‬K       C=O    ‫א‬‫א‬‫א‬‫א‬
                                                                                   O

 EArF،R R(Ar)-C-H W ‫א‬‫א‬
                                                                           
                                                      O

  R , R  R
                                                      C      R
                                                                     
                                                                   W‫א‬‫א‬‫א‬K
                                                                                                             K


                                                          W‫א‬‫א‬‫א‬7J 2
  KIUPAC‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬

                                                                                              W‫א‬‫א‬

                                                                                                          
                                                                                            W‫א‬‫א‬J 
                                                                
 J ic acid‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬
 ‫א‬‫א‬aldehydeE‫א‬‫א‬ ‫א‬F
                                                                                         
                                                                                                       K‫א‬
                                                                                                                 
                            O
                                                ‫א‬‫א‬                        Formic acid
                 H          C        H
                     Formaldehyde
                             O

                                                ‫א‬‫א‬
                CH 3         C       H                                            Acetic acid
               Acetaldehyde
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                               (C    C      C      C        O)
                                          


                                                          - ٩٣ -
   ‫א‬‫א‬                                      ١٤٠                                           ‫א‬
  ‫א‬‫א‬‫א‬                          ‫א‬‫א‬                           ‫א‬



                                                                 
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                      W‫א‬‫א‬
                                                 CH2CH3                     O

                                       CH3      CH           CH             C        H
                                                 B

                                                             CH3
                               
                                             Dimethyl Valeraldehyde

                                                                                                               
                                                                                                W‫א‬J 
                                                        
F‫א‬‫א‬‫א‬‫א‬‫א‬ 
                                                          Wketone‫א‬E‫א‬‫א‬
                                   O                                             O

                     CH3           C      CH3                         CH3        C           CH( CH3)2
                           Dimethyl ketone                             Methyl isopropyl ketone
                                                             
                       ( acetone )
 Phenyl ‫א‬‫א‬‫א‬phenone‫א‬
   W‫א‬‫א‬‫א‬‫א‬‫א‬E-oic acid F-ic acid
                                   O                                                     O

                                   C         CH3                                     C

                          Acetophenone                                        Benzophenone


                                                                                                  W‫א‬‫א‬

                                                                                                               
                                                                                                W‫א‬‫א‬J 
،‫א‬‫א‬J al‫א‬‫א‬‫א‬J e ‫א‬‫א‬‫א‬
–KK‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                  
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
                                                                                                      W‫א‬‫א‬
                                                         - ٩٤ -
    ‫א‬‫א‬                                       ١٤٠                                               ‫א‬
   ‫א‬‫א‬‫א‬                           ‫א‬‫א‬                               ‫א‬


                                  O                                                  CH3                  O

                          CH3     C       H                               CH3        CH      CH2          C      H
                               Ethanol
                                                                    3-Methyl butanal
                                            
‫א‬‫א‬‫א‬
                                                                K‫א‬
                                      O                                                          O

                                                                                                 C       H
                                      C       H

                               Benzaldehyde                                  CH 3

                                                                               p-tolualdehyde


                                                                                                      W‫א‬–
‫א‬‫א‬‫א‬‫א‬‫א‬
                                      
‫א‬J e‫א‬EJ alFJ one ‫א‬،‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬IUPAC‫א‬‫א‬‫א‬
                                                                     K‫א‬‫א‬‫א‬
                          O                            O                                             O

            CH3           C        CH3                                    CH2         CH             C        CH3
                      Propanone                                                      3-buten-2-one
                                              Cyclopentanone


                                                      W‫א‬‫א‬‫א‬‫א‬‫א‬7J 3
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                          + -
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                         C=O

‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬

                                                           - ٩٥ -
   ‫א‬‫א‬                                              ١٤٠                                       ‫א‬
  ‫א‬‫א‬‫א‬                                 ‫א‬‫א‬                        ‫א‬



                                          
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K
                                                                                                                    K‫א‬
                                                                                   O
                                                   C        O             H             H




                                      
                                                ‫א‬
                                                                 W‫א‬‫א‬‫א‬‫א‬‫א‬
Formalin‫א‬،‫א‬‫א‬‫א‬‫א‬
‫א‬K‫א‬‫א‬،E٪37F
                  
،‫،א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬،‫א‬‫א‬،56
                                                                                                    K‫א‬‫א‬
                                                                      W‫א‬‫א‬‫א‬7J 4
                                                          W‫א‬‫א‬‫א‬‫א‬–
                                                                                        W‫א‬             K 
،‫א‬‫א‬‫א‬‫א‬‫א‬
                                           ‫א‬‫א‬‫א‬K‫א‬
                                                                                            O
                                                                Cu /
                             CH3CH2CH2OH                                       CH3CH 2C            H
                                               o
                                1-Propanol (1)                                          Propanal
                         
                                  OH                                          O
                                                                                                   +3
                                                   H2Cr 2O7
                             CH3CHCH 3                                 CH3C             CH3 + Cr
                                           o
                             2-Propanol (2)                                 Acetone
                         
                                                            W‫א‬‫א‬                      K 

                                                                 - ٩٦ -
    ‫א‬‫א‬                                          ١٤٠                                              ‫א‬
  ‫א‬‫א‬‫א‬                               ‫א‬‫א‬                             ‫א‬



‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                               
‫א‬‫א‬E‫א‬F‫א‬
                                  W‫א‬‫א‬‫א‬
                                        O                                             O
                                                          AlCl3
                           + CH3CH2C            Cl                                    C         CH2CH3 +     HCl

                                                                           Ethyl phenyl ketone

                K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

                                                                                             
                                                 W‫א‬‫א‬‫א‬‫א‬J 
                                                                                  W‫א‬‫א‬‫א‬ K١
            
‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                           W‫א‬‫א‬
                                                                   O                                         (1
                                    CuO-Ag
        2CH 3OH           + O2              O        2H            C         H        + 2H 2O
                                   500-650 C

                                                                                  O
                                                                                                             (2
                                                PdCl2
        CH2              CH2 +     1/2 O2                         CH3            C          H
                                                H 2O
   
                                                                                  W‫א‬‫א‬ K٢
          K‫א‬500 CO‫א‬‫א‬2-propanol‫א‬‫א‬
                                                                                            O
                                                      Cu as Cat.
                           (CH3)2CHOH                         O
                                                                         CH3                C      CH3
                                                          500 C
                            2-Propanol                                                Acetone
                      

                                                            W‫א‬‫א‬‫א‬7J 5
                                  
،‫א‬‫א‬‫א‬‫א‬ 
‫א‬‫א‬‫א‬‫א‬K‫א‬

                                                              - ٩٧ -
   ‫א‬‫א‬                                             ١٤٠                                                 ‫א‬
  ‫א‬‫א‬‫א‬                                 ‫א‬‫א‬                                 ‫א‬



‫א‬EF‫א‬،‫א‬
                                                                              W‫א‬‫א‬‫א‬‫א‬

                          .(Cyanohydrine )HCN‫א‬ .١
                                       O                                                            OH
                                                                       -
                                                                      CN
                      CH3              C       H   +     HCN                          CH3           C        H

                                                                                                    CN
                                                                                    Acetaldehyde cyanohydrine

                                   O
                                                                          -                                  OH
                                                                         CN
                     CH3           C       CH3     +    HCN                               CH3           C        CH3
                                                                                                             CN
                                                                                            Acetone cyanohydrine
             

                                                                                       W‫א‬‫٢. א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                           WG-NH2
                               O
                                            NH Ar              OH       H=G
                     C NH 2              
               NH

                                                                    
‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
‫א‬‫א‬K‫א‬‫א‬‫א‬
                                                                             
F‫א‬‫א‬‫א‬
                  K‫א‬‫א‬‫א‬ E‫א‬
                           O
                                                                         +         CH 3
                                                                         H
                 CH 3      C       CH 3    +             NHNH 2                            C    N       NH
                                                                                   CH 3

                                                                                   Acetone Phenylhydrazene


                                                                - ٩٨ -
   ‫א‬‫א‬                                      ١٤٠                                       ‫א‬
  ‫א‬‫א‬‫א‬                          ‫א‬‫א‬                       ‫א‬



                                                                                    WReduction‫א‬‫٣. א‬
                                                
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
           KNaBH4‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                    OH
                                 O                          H2/Pt
                                                                            CH 3    CH      CH 3
                     CH3         C       CH 3
                                                        1)NaBH 4
                                                                            CH 3     CH      CH 3
                                                        2)H 2 O
                                                                                     OH


                                                                              2-Propanol

                                                                                    WOxidation‫٤. א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬                                      
                                                                                           K‫א‬
                                     O                                         O
                                                       (O)
                             R       C      H                           R      C      OH
                         
                                                        
                                                                                                             
                                                                                                                   
                                                                                                                   
                                                                                                                   
                                                                                                                   
                                                                                                                   




                                                         - ٩٩ -
 ‫א‬‫א‬                                                    ١٤٠                                             ‫א‬
‫א‬‫א‬‫א‬                                       ‫א‬‫א‬                           ‫א‬



                                              E‫א‬‫א‬F
                                                                                                 W‫א‬‫א‬ .١
                       O                                                                        O
                                   Cl
                                                           (2                        CH 3CH 2C          H     (1
                                                                                
            
                                    O                                                       O

                                    C         H
                                                            (4                  (CH 3)2CHCCH(CH 3)2                 (3
           
                                                                                                   O

                                                                                    CH 3CH 2CH 2 CCH 3             (5
                                                                           
                                                                                                                         

                                                                          W‫א‬‫א‬‫א‬‫٢. א‬
                                                                                                                                 
                Acetophenone                              (2                         Benzaldehyde         (1
                 Benzylphenyl ketone                       (4                          Benzophenone         (3
                 3-Pentanone                                (6                        Butanal                (5
                                                                                             W‫א‬‫א‬ .٣
                                                                                                                                     

                               O                                                            O
                                                                ?                                                       (1
                               C        Cl      +                                           C


                               O

          CH 3 CH 2 CH 2 C          H
                                                1) NaBH 4

                                                2) H3O
                                                       +                                ?                               (2

                               O
                                             1) NaBH 4
                                                    +
                                                                                     ?                                  (3
                                             2) H3O


                   O

           CH 3 C CH 3
                                              NH 2 OH
                                                                                    ?                                   (4
                   O

           CH 3 C          H
                                              Oxidation.
                                                                                     ?                                  (5
                       O

           CH 3 CH 2 C         H
                                               H 2 / Pt
                                                                                        ?                               (6
                                                                      - ١٠٠ -
 ‫א‬‫א‬                             ١٤٠                                              ‫א‬
‫א‬‫א‬‫א‬                 ‫א‬‫א‬                              ‫א‬



                               E‫א‬‫א‬F
                                                                                          WE1F‫א‬‫א‬
                       . 2-Chlorocyclohexanone (2                                     . Propanol               (1
                                                                           . Methyl propyl ketone              (3
                                                                                          WE2F‫א‬‫א‬‫א‬
                                          O                                                       CHO
                                                                                                              (1
                           CH3 CH2 CH2 C-H              (4
                                                                                  
                                                                                                O
                                                                               CH3 CH2 CH2 C-CH3             (6
                                                                         
                                                                                          WE3F‫א‬‫א‬‫א‬
                                     N-OH
                                                         (4          
                                                                             CH3 CH2 CH2 CH2 OH              (2
                               CH3 -C- CH3
                           
                                                                                               OH
                                                                                       CH3 CH2 C CH3         (6
                                                                               
                                                                                                             

                                                                                                             




                                             - ١٠١ -
                                                               ‫א‬‫א‬‫א‬
                                                            ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                                                ‫א‬‫א‬‫א‬‫א‬




                                       ‫ א‬‫א‬
                                                ‫א‬
                                  ‫א‬‫א‬
 ‫א‬‫א‬




٨
       ‫א‬‫א‬                              ١٤٠                                   ‫א‬
 ‫א‬‫א‬
                                            ‫א‬‫א‬                   ‫א‬



                                                                                                   W‫א‬‫א‬
                                                        
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬     
                                                               K‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                               
                                                                                      W‫א‬‫א‬
                                               W‫א‬‫א‬‫א‬
                                                    K‫א‬‫א‬ .١
                    K‫א‬‫א‬‫א‬‫א‬ .٢
                                                                                                               
                                                                                 W‫א‬‫א‬‫א‬
                                                     K٪80‫א‬‫א‬‫א‬
                                                                                                               
                                                                                      W‫א‬‫א‬
                                                                                                K
                                                                                                               
                                                                                   W‫א‬‫א‬
                                                         KOverhead Projector  .١
                                                                                              K .٢


                                                                                         W‫א‬‫א‬
                                                                         K‫א‬‫א‬‫א‬‫א‬
                                                                                                               
                                                                                                               




                                                    - ١٠٢ -
        ‫א‬‫א‬                         ١٤٠                                   ‫א‬
  ‫א‬‫א‬
                                        ‫א‬‫א‬                   ‫א‬



                                                                      W8J 1
          
 EJ COOH)‫א‬‫א‬‫א‬
                                                                    
 KE-OHF‫א‬EC=OF‫א‬‫א‬K
                                          
 ،‫א‬‫א‬‫א‬
                                                              K‫א‬‫א‬


                                                                     W‫א‬‫א‬8J 2
                                                                                W‫א‬‫א‬J ‫א‬
                                        
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
               KE8J 1FKW‫א‬‫א‬‫א‬‫א‬K

                 WE‫א‬‫א‬‫א‬E8J 1FF
                      ‫א‬                 ‫א‬                      ‫א‬‫א‬
            ‫א‬،Formic                                          Formic acid
                                              HCOOH
             K‫א‬                                           ‫א‬
               Acetum
                                                                           Acetic acid
              ‫،א‬‫א‬‫א‬
                                          CH3COOH                             
              ‫א‬‫א‬
                                                                           ‫א‬
                   K‫א‬
               ،Butyrum                                        Butyric acid
                                        CH3(CH2)2COOH
             K‫א‬‫א‬‫א‬                                     K‫א‬
                                                                                                           
 β،α‫א‬‫א‬،‫א‬‫א‬
 ‫א‬‫א‬α‫א‬‫א‬‫א‬‫א‬KKKγ،
 K‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                           
                                                                                                           

                                                - ١٠٣ -
       ‫א‬‫א‬                                    ١٤٠                                                ‫א‬
 ‫א‬‫א‬
                                                  ‫א‬‫א‬                                ‫א‬




                                                       ‫א‬‫א‬                                             O
                                                                                                      α     γ   β    α
                                                                                            C         C     C   C    C    C       OH
                                                      ‫א‬‫א‬                         5     4    3   2    1



                                                                                                                           W
                                                     CH3         CH3

                                            CH3      CH          CH           COOH
                                  2,3-Dimethylbutanoic acid                                              
                                  α،β -Dimethylbutyric acid                                             


                                                                                                            
                                                                                  WIUPAC ‫א‬‫א‬W
‫א‬‫א‬‫א‬e‫א‬oic acid ‫א‬
‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬
،‫א‬‫א‬‫א‬‫א‬
                               W‫א‬‫א‬‫א‬‫א‬‫א‬
                                       O                                               Br

                                                                              CH3      CH        COOH
                           CH3         C     OH
                                                                              2-Bromopropanoic acid
                                 Ethanoic acid
                                 (Acetic acid)
                                                                                        COOH

                                   CH3

                     CH3           C       CHCOOH
                                                                                    Cyclohexane
                         3-Methyl-2-butenoic acid                                   Carboxylic acid




                                                                                                                                  



                                                          - ١٠٤ -
      ‫א‬‫א‬                                  ١٤٠                                      ‫א‬
‫א‬‫א‬
                                               ‫א‬‫א‬                    ‫א‬




                                                                                        WW

       W‫א‬‫א‬‫א‬‫א‬ ‫א‬‫١. א‬
                          COOH                       OH                                CH3
                                                              COOH




                   Benzoic acid               Salicylic acid
                                                                                       COOH

                                                                                   P-Toluic acid
                                                                                      K

       ‫א‬ ‫א‬ .٢
                                                                                           W
                                               COOH
                               COOH                                        COOH
                                                                                           COOH
                                               CH2
     COOH                                                                  (CH2)4                     COOH
                               CH2
                                               CH2
     COOH                                                                  COOH
                               COOH
                                               COOH

     Oxalic acid Malonic acid                  Succinic acid Adipic acid                 Phthalic acid

       ‫א‬،Fatty acids‫א‬‫א‬ .٣
                               
       ‫א‬،2612‫א‬‫א‬‫א‬
                                                               
       ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                               ‫א‬
                        CH 3 (CH 2)14 COOH            CH3 (CH 2)16 COOH
                                                                                                W
                           Palmitic acid                      Stearic acid
                                                                                                              



                                                       - ١٠٥ -
       ‫א‬‫א‬                                   ١٤٠                                        ‫א‬
 ‫א‬‫א‬
                                                 ‫א‬‫א‬                      ‫א‬



                                                     W‫א‬‫א‬‫א‬‫א‬8J 3
،‫א‬‫א‬‫א‬
                                                     
‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬
 
‫א‬‫א‬‫א‬‫א‬،‫א‬
                                          W‫א‬‫א‬،‫א‬
               KO100،L46Z‫א‬‫א‬                        HCOOH       Formic acid

            KO78،L46Z‫א‬‫א‬                           C2H5OH        Ethanol

‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                         
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                                                                         K‫א‬
                                                   _       +
                                                  O       H         O
                                     R      C                                C   R
                                                            +        _

                                                O        H         O
                                 E‫א‬‫א‬‫א‬F
                                                                  W‫א‬‫א‬8J 4
‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                              K‫א‬‫א‬
                                                                                     _
                                                  H2O                    +
                              HCl                   H3O + Cl
                           
‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                 K‫א‬‫א‬
                                                                                  _                 +

           
                RCOOH           + H2 O                                       RCOO        + H3 O


                                                         - ١٠٦ -
            ‫א‬‫א‬                              ١٤٠                                      ‫א‬
      ‫א‬‫א‬
                                                 ‫א‬‫א‬                      ‫א‬



               ‫א‬‫א‬‫א‬‫א‬‫א‬
           ‫א‬‫א‬K‫א‬‫א‬‫א‬
                            W‫א‬‫א‬‫א‬‫א‬
                                         _
                                         O                         O                       O
                                                                                            _
                              R      C              R        C                   R     C
                                                                       _
                                         O                         O                       O
                       

                                                        W‫א‬‫א‬‫א‬‫א‬‫א‬

                               WElectron-withdrawing group‫א‬‫١. א‬
             ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
             ‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
                                                W‫א‬
                    ....., -COOH , -SO3H , -CN , -NO2 , Br , Cl ,F
    Benzoic acid p-Nitro Benzoic acid‫א‬
                                               KPara‫א‬‫- א‬NO2

                                       :Electron-donating group‫א‬‫٢. א‬
    ،‫א‬‫א‬‫א‬‫א‬‫א‬
           
    ،‫א‬‫א‬‫א‬
                                                                                                      W
                                              -OH , -NH2 , -OCH3 , -CH3
                              
    ‫א‬‫א‬‫א‬‫א‬
                 K‫א‬‫א‬‫א‬‫א‬J CH3‫א‬
    ‫א‬‫א‬‫א‬‫א‬‫א‬
         
    ‫א‬‫א‬‫א‬EInductetive effectF
‫א‬EpKaF‫א‬‫א‬‫א‬
                                                                            WEChlorobutyricF

                                                         - ١٠٧ -
       ‫א‬‫א‬                                       ١٤٠                                    ‫א‬
 ‫א‬‫א‬
                                                    ‫א‬‫א‬                     ‫א‬



                                               Cl                         Cl                Cl

                                     CH3CH2CHCOOH                   CH3CHCH 2COOH           CH2CH2CH2COOH
    CH 3CH 2CH 2COOH
     PKa = 4.82                            PKa = 2.85                  PKa = 4.05                PKa = 4.52

     Z1                  W         92                  W               6      W            2
       ‫א‬
                           
‫א‬Ka‫א‬‫א‬‫א‬
                                                                          W‫א‬‫א‬‫א‬ pKa
                                              _     +                                                                    
                                         [ RCOO ] [ H ]
                         Ka      =          [ RCOOH ]

                                _ log Ka = pKa
                                                                  K‫א‬pKaKa‫א‬
                                                    ‫ﺗﺰداد اﻟﺤﻤﻮﺿﺔ‬        Ka     ‫زﻳﺎدة‬
                                                    ‫ﺗﻘﻞ اﻟﺤﻤﻮﺿﺔ‬        pKa      ‫زﻳﺎدة‬
                   
                                                                     W‫א‬‫א‬‫א‬‫א‬
           ‫א‬                      pKa                            Ka        ‫א‬
                                   3.74                        1.77*10-4           HCOOH
                                           4.47                        1.76*10-5        CH3COOH
                                           4.85                        1.43*10-5       CH3CH2COOH


                                                          W‫א‬‫א‬8J 5
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 W‫א‬‫א‬‫א‬،‫א‬‫א‬




                                                             - ١٠٨ -
               ‫א‬‫א‬                                         ١٤٠                                        ‫א‬
         ‫א‬‫א‬
                                                               ‫א‬‫א‬                        ‫א‬



                                                                             W‫א‬‫א‬‫א‬‫א‬ .١
                                                   O
                                                                     H2Cr 2O7                               +3
        RCH 2       OH                                                                                                 ( ‫) أﺧﻀﺮ اﻟﻠ ﻮن‬

                                 OR        R     C         H                               RCOOH      +    Cr

                                                                                                        W‫א‬ .٢
        ‫א‬‫א‬.(Ar)R-CN‫א‬‫א‬
                                                 K‫א‬‫א‬‫א‬
                                                                                                             _
                                                                                                           CN      
                                                                                                                   
                                                                                                  R-X                            RCN

                                                                                                                                       

                                                                   K‫א‬‫א‬‫א‬

                                                       +
                                                 H3O       ,                       +
                                  RCN                                   RCOOH + NH 4
                             
                                                                                              W‫א‬ .٣

                                                                                                                                       
                                               R
                                                                KMnO4 ,
                                                                                                 COOH

                                               C2H5

                                                                KMnO4 ,


                                         Ethyl benzene                                     Benzoic acid
                                                                        
                                                                        
                                                                        
                                                                        

                                                                       - ١٠٩ -
       ‫א‬‫א‬                               ١٤٠                                      ‫א‬
 ‫א‬‫א‬
                                             ‫א‬‫א‬                      ‫א‬



                                                                         W‫א‬‫א‬ 8J 6
                                     
‫א‬ K ‫א‬‫א‬‫א‬
                                                                                      K‫א‬‫א‬

                                 W‫א‬‫א‬‫א‬‫א‬‫١. א‬
                                                                             _
                                                                                 +
                         CH3COOH + NaOH                            CH3COO Na + H 2O
                         Acetic acid                             Sodium acetate
                  
                                                                            _ +
                         Ph COOH + NaOH                             Ph COO Na + H 2O

               Benzoic acid                     Sodium benzoate
                           
،‫א‬‫א‬‫א‬‫א‬
                                                                                        W‫א‬‫א‬
                                                                            _    +
            (Ar) R COOH + NaHCO 3                             (Ar) R COO Na + H 2O + CO2
       
                                  K‫א‬،‫א‬‫א‬‫א‬

                                          W،‫א‬‫א‬ .٢
                  RCON
‫א‬‫א‬RCOOR‫א‬‫א‬RCOCl‫א‬‫א‬
                                                                            O                           
                                                                   K‫א‬
                                                                     R-C-O-C-R


                                                     W‫א‬‫א‬8- 7
E-OHF‫א‬‫א‬‫א‬‫א‬
‫א‬–NH2Cl-RCOO-J OR‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                               W‫א‬‫א‬‫א‬‫א‬‫א‬
                                                     - ١١٠ -
       ‫א‬‫א‬                                         ١٤٠                                          ‫א‬
 ‫א‬‫א‬
                                                       ‫א‬‫א‬                          ‫א‬



                 ‫א‬                                            ‫א‬‫א‬
                         O                                                                                        O
                                                                              ‫א‬
        CH3 C                   Cl       Acetyl chloride
                                                                                                       R         C      X
                    O                                                                                           O
                                                                                    
      CH3 C                 OC2H5            Ethyl acetate                                            R       C     OR
                             O
                                                                                                               O
                             C       NH2                                       ‫א‬
                                                                                                                      NH2
                                               Benzamide                                            R         C
      
              O                  O                                                                        O              O
                                                                             ‫א‬
   CH3        C     O            C    CH3           Acetanhydride                                 R       C   O          C       R
                    O                                                                                         O       _
                                 _
                                      +                                     ‫א‬                                        +
      CH3 C                     O Na Sodium acetate                                                R        C       O M


                                                                ‫א‬‫א‬7J 8J 1

                                                                                :Acid halides ‫א‬‫א‬W
،-yl halide‫א‬‫א‬‫א‬ - ic acid‫א‬
                                                                                                                W‫א‬‫א‬
                                          O                                                  O
                             CH3          C   OH                                    CH3      C      Cl

                                      Acetic acid                                       Acetyl chloride


                     
                                                                                        :Esters ‫א‬‫א‬W
                      
‫א‬‫א‬‫א‬،-ate‫א‬‫א‬‫א‬ -ic acid‫א‬
                WKE‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬

                                                               - ١١١ -
       ‫א‬‫א‬                                   ١٤٠                                     ‫א‬
 ‫א‬‫א‬
                                                 ‫א‬‫א‬                     ‫א‬



                                   O                                                 O
                            CH3    C       OH                                CH3     C     OC2H5

                           Acetic acid                                        Ethyl acetate
                                                                                      WAmides‫א‬‫א‬W
                             WKamide‫א‬‫א‬‫א‬J oicAcid‫א‬
                                       O                                                   O
                    CH3 CH2            C    OH                               CH3 CH2       C   NH2

                        Propanoic acid                                          Propanamide

            
                                                            WAcid anhydrides‫א‬‫א‬W‫א‬
                                                                         .anhydrideacid‫א‬
                                  O                                              O   O
                                  C O OH                                         C O C


                            Benzoic acid                                     Benzoic anhydride
                
                                                                         :Acid salts‫א‬W
                                              
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                                                                     K‫א‬‫א‬
                                   O                                             O     _   +
                            CH3    C       OH                           CH3      C   O NH 4

                            Acetic acid                                  Ammonium acetate
                        
                                                          
                                                          

                                                         - ١١٢ -
        ‫א‬‫א‬                               ١٤٠                                   ‫א‬
  ‫א‬‫א‬
                                              ‫א‬‫א‬                  ‫א‬



                                       W‫א‬‫א‬‫א‬‫א‬‫א‬7J 8J 2
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                  
‫א‬‫א‬،‫א‬‫א‬‫א‬ 
K‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬‫א‬
                                                 K‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬، ‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                       _                             O
                           O                           O
                                 ..                       +                          C
                          R-C-NH 2                 R-C = NH 2              ,             .. +
                                                                                R        NH2
                   
                           ‫א‬‫א‬                                ‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬          
                                                                 K‫א‬




                                                      - ١١٣ -
          ‫א‬‫א‬                                  ١٤٠                                       ‫א‬
    ‫א‬‫א‬
                                                   ‫א‬‫א‬                       ‫א‬



                                                        W‫א‬‫א‬7J 8J 3
                                                          K‫א‬
                                                               O
                                                       R      C      Cl

                                                                  SOCl 2
                                                                 in Benzene


    O              O                                           O                                               O
                                                                                    ROH
R   C      O       C        R                          R      C      OH                                  R     C        OR
                                                                                       +
                                      SH 2SO 4                                        H
    Acid anhydride                                           Acid                                              Ester


                                                   NH 3                NaOH
                                      O                                              O     _   +
                                R     C     NH 2                               R     C     O Na
                                                                                   Acid salt
                                    Amide

                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                                                                                    
                                                           - ١١٤ -
      ‫א‬‫א‬                                     ١٤٠                                      ‫א‬
‫א‬‫א‬
                                                  ‫א‬‫א‬                      ‫א‬




                                       E‫א‬‫א‬F
                                                                                       W‫א‬‫א‬ K١
                                      O                                               CO 2H
                                                                  2)                       OH
           1)           CH 3 CH CH C          OH

                               OH NH 2
                                                                                      NH 2

                                          O                                                O
                                              _      +
                        CH3 CH2 CH 2 C O NH 4                     4)          CH 3 CH 2 C      OCH 3
           3)
                                  O           O                                   O
                                                                                               CH 3
           5)                     C      O    C       CH 3        6)          H   C    N
                                                                                               CH 3

                                  O                                                            O
           7)           CH 3 CH 2 C      Cl
                                                                  8)          CH3 CH 2 CH 2 C         NH 2

                                               W‫א‬‫א‬‫א‬‫א‬‫ א‬K٢
a) 2,3-dibromopentanoic acid.
b) Methyl benzoate.
c) Methyl formamide.
d) m-nitrobenzoyl chloride.
e) Potassium formate.
f) N,N-diethylpropanamide.
g) Benzoic formic anhydride.
h) Ethyl 2-aminopropanoate.
                                  ‫؟‬‫א‬‫א‬‫א‬ K٣
                                                                   K‫א‬‫א‬                       K 
                                                        K‫א‬‫א‬                          K
                                                                    K‫א‬‫א‬                     K
                                                K‫א‬‫א‬                            K
                                                    K‫א‬‫א‬                            K 

                                                          - ١١٥ -
      ‫א‬‫א‬                                ١٤٠                                  ‫א‬
‫א‬‫א‬
                                             ‫א‬‫א‬                  ‫א‬



                                                                             W‫א‬‫א‬ K٤
                                                               +

          1)                            CN
                                                    H 2O / H
                                                                                                 ?
          2)              CH3                     CH 2H5
                                                                         KMnO 4
                                                                                                 ?
                                    O
          3)            CH3CH2 C        OH
                                                          SOCl 2
                                                     Benzene
                                                                                                ?
                               O
           4)           CH3 C       OH
                                                      H
                                                          +
                                                                                               ?
                                O

           5)           2CH3 C CH3                                                            ?
                                                      H2SO4



                                                      
                                                      
                                                      
                                                      
                                                      
                                                      
                                                      
                                                      
                                                      
                                                      
                                                      
                                                      

                                                     - ١١٦ -
       ‫א‬‫א‬                                  ١٤٠                                           ‫א‬
 ‫א‬‫א‬
                                                ‫א‬‫א‬                           ‫א‬




                                      E‫א‬‫א‬F
                                                                                                     WE1F‫א‬‫א‬
           2) 4-Amino-2-hydroxy benzoic acid.
           4) Methyl propanoate.
           5) Acetic benzoic anhydride.
           7) Propanoyl chloride.
                                                                                                     WE2F‫א‬‫א‬
                         O
                   H-C-NHCH 3          (3                        CH 3 -CH2-CH-CH-COOH                        (1
                                                                                   Br Br
                    O _                                                                    O    O
                         +
                  H-C-O K              (5
                                                                                        -C-O-C-H             (7
                                                                                                     WE3F‫א‬‫א‬‫א‬
                                               
‫א‬‫א‬‫א‬ K١
‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                             K‫א‬
                                  O                                              O
                                                                +                      _
                                 H-C-OH                       H       + H-C-O
                             
                                                                             ‫א‬‫א‬‫א‬
                                                                                   
                                                                                 
                                                            +
                                         KE H ‫א‬،‫א‬F
                    O                                               O       _
                                            +
           CH3-C-OH                         H        + CH3-C-O                     " ‫" اﻟﻘﺎﻋﺪة اﻟﻤﺮاﻓﻘﺔ‬
                                                                           
?‫א‬?E‫א‬‫א‬CH3F
                                                                                      KEH+‫א‬F

                                                        - ١١٧ -
       ‫א‬‫א‬                        ١٤٠                            ‫א‬
 ‫א‬‫א‬
                                      ‫א‬‫א‬            ‫א‬



‫א‬،‫א‬‫א‬ K٢
                                                                              
‫א‬‫א‬،‫א‬‫א‬‫א‬
                                           K‫א‬‫א‬‫א‬
                                                                           WE4F‫א‬‫א‬‫א‬
                         O
                                                      HOOC            COOH           (2
             CH3-C-O C 2H5 (4
                                                                                                  




                                              - ١١٨ -
                                  ‫א‬‫א‬‫א‬
                               ã¹]<gè…‚jÖ]æ<ËÖ]<Üé×Ãj×Ö<íÚ^ÃÖ]<퉉ö¹]
                                   ‫א‬‫א‬‫א‬‫א‬




          ‫ א‬‫א‬
                   ‫א‬
                  ‫א‬
‫א‬




٩
     ‫א‬‫א‬                          ١٤٠                                  ‫א‬
        ‫א‬                        ‫א‬‫א‬                   ‫א‬



                                                                                     W‫א‬‫א‬
  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                K‫א‬‫א‬‫א‬
                                                                                                      
                                                                                     W‫א‬‫א‬
                                                W‫א‬‫א‬‫א‬
                                                                             K‫א‬ .١
                                             K‫א‬‫א‬‫א‬ .٢
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫٣. א‬
                                                                                                      
                                                                              W‫א‬‫א‬‫א‬
                                                 K٪90‫א‬‫א‬‫א‬
                                                                                                      
                                                                                W‫א‬‫א‬
                                                                                           K
                                                                                                      
                                                                                 W‫א‬‫א‬
                                                      KOverhead Projector  .١
                                                                                        K .٢
                                                                                                  
                                                                                   W‫א‬‫א‬
                                                                     K‫א‬‫א‬‫א‬‫א‬




                                                 - ١١٩ -
   ‫א‬‫א‬                                  ١٤٠                                              ‫א‬
      ‫א‬                                ‫א‬‫א‬                            ‫א‬



                                                                                                 W8-1
EF‫א‬ ‫א‬
‫א‬KEFEF‫א‬
‫א‬‫א‬KEF‫א‬‫א‬‫א‬‫א‬
                          K‫א‬RR3N , R2NH , RNH2‫א‬‫א‬
                            
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬
‫א‬E‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬
         K‫א‬‫א‬‫א‬
                                                                                   W‫א‬8-2

                                                                                                 W‫א‬8-2-1
                       W‫א‬‫א‬‫א‬
             3O      2O                     1O
             ‫א‬         ‫א‬
           ‫ א‬‫ א‬ K‫א‬
                  K‫א‬                    K
                 (C2H5)3N              (CH3)2NH                            CH3NH2                      
                 Triethylamine        Dimethylamine                       Methylamine              
                                                                                                
                             N                    NHCH3                                NH2
                                                                                                    
                      Pyridine        N-Methyl aniline                      Aniline



                                                                                                                        




                                                       - ١٢٠ -
   ‫א‬‫א‬                                    ١٤٠                                         ‫א‬
      ‫א‬                                  ‫א‬‫א‬                          ‫א‬




                                                                                                   W‫א‬8-2-2
                                                                                        W‫א‬‫א‬W
‫א‬amine‫א‬‫א‬‫א‬‫א‬
                                                                                                    W‫א‬‫א‬
                                                               CH3                          CH3
                      CH3NH2
                                       o           CH3         NH                  CH3       N     CH3
                                                                           o
                 Methylamine (1)                                                                       o
                                                  Dimethylamine (2)
                                                                                   Trimethylamine (3)

                              CH3                                 CH3
              CH3CH2CHNH2                      CH3CH2             N        CH3
                                           o                                   o
                 sec-Butylamine (1)            Ethydimethylamine (3)

                           W‫א‬‫א‬‫א‬‫א‬
                                                             NH2
                                                     Cl                                      NH(CH3)
                                                                      Cl
                           NH2
                                  NO2

                                                             Cl
                      O-Nitroaniline               2,4,6-Trichloroaniline            N-Methylaniline
‫א‬‫א‬‫א‬‫א‬‫א‬


                                                CH3                        NH2

                                                          p-Toluidine


                                  KP- Toluidine‫א‬Toluidine‫א‬Aminotoluene
‫א‬،‫א‬‫א‬‫א‬‫א‬
                                                              W‫א‬‫א‬




                                                           - ١٢١ -
   ‫א‬‫א‬                                    ١٤٠                                          ‫א‬
      ‫א‬                                  ‫א‬‫א‬                           ‫א‬




                      N                                                        N
                                     N                    N                                            N
                      H                                                        H
                                     H
              Pyrrolidine                                                    Pyrrole           Quinoline
                                  Pipyridine          Pyridine
                                                                                             W‫א‬‫א‬W
‫א‬‫א‬‫א‬IUPAC‫א‬‫א‬‫א‬
‫א‬‫א‬Amino
‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                           W‫א‬
                                    CH3                                 CH3 CH CH2 CH            CH3
            CH3 CH2 CH CH2 CH CH3                                              NH2
                            NH2

               5-Methyl -3-aminohexane
                                                                         2-Amino-4-phenylpentane
                      H2N CH2 CH2 CH2 COOH                             CH3 CH          NH    CH2 CH3

                          4-Aminobutanoic acid                                 CH2CH2CH2CH3

                                                                        2-(N-Ethyl amino)hexane
                                  COOH




                                  NH2

                          P-Aminobenzoic acid
                                                                                              W‫א‬W
EAmmoniumFEAmineF‫א‬‫א‬‫א‬‫א‬
                                     
‫א‬‫א‬‫א‬‫ א‬‫א‬(Anilinium)EAnilineF‫א‬
                                                                                                              W‫א‬

                                                         - ١٢٢ -
    ‫א‬‫א‬                                    ١٤٠                                       ‫א‬
       ‫א‬                                  ‫א‬‫א‬                        ‫א‬



                                                                                       + _
                                                                                      NH3 Br
                                    CH3          _
                                        +
                              CH3-N-CH 3 I
                                    CH3
                           Tetramethylammonium                                 Anilinium bromide
                       

                                                                         W‫א‬‫א‬‫א‬8J 3
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ 
   (C2H5)2NH, (CH3)3N, (CH3)2NH, WEF‫א‬‫א‬
 J ٤F‫א‬‫א‬‫א‬‫א‬CH3NH2
 ‫א‬E11FE١١
                                                                       
                                             K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬K
                                                           
 ‫א‬‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬‫א‬
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                                    KE8-1F‫א‬
          K‫א‬‫א‬‫א‬‫א‬‫א‬E8-1F‫א‬
            ‫א‬                                                                                   
                              ‫א‬       ‫א‬‫א‬
              ‫א‬
                           - 42                   44                     Propane         CH3CH2CH2
                           17                     45                    Ethylamine       CH3CH2NH2
                             7.5                   45              Dimethylamine          CH3NHCH 3
                             78                    46               Ethyl alcohol         CH3CH2OH
                           100.5                   46                Formic acid
                                                                        HCOOH
      
 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬،‫א‬‫א‬K‫א‬‫א‬‫א‬،
                                                          - ١٢٣ -
       ‫א‬‫א‬                                  ١٤٠                                         ‫א‬
          ‫א‬                                ‫א‬‫א‬                          ‫א‬



                                                                         W‫א‬8- 4
   ،‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                                       
   ‫א‬‫א‬‫א‬
                                                                      K‫א‬‫א‬
                                                                                              _
                                                                                      +
                         RNH 2 + HX
                                                                          [ RNH 3 ] X
   ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬
           ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
   ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                                                                   W‫א‬‫א‬

                   . NH2                     +
                                            NH2
                                                                           +
                                                                          NH2
                                                                                                  +
                                                                                                  NH2


                                     [        _

                                                                          _
                                                                                          _
                                                                                                           ]
                                         Resonance structures of aniline
                                      E‫א‬‫א‬‫א‬F
   ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                 K‫א‬–SO3H‫א‬–NO2‫א‬
                                        
   ‫א‬‫א‬‫א‬‫א‬
                                                             
   ‫א‬‫א‬،‫א‬‫א‬–OCH3‫א‬
                 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                             NH2                     NH2                        NH2


                                     >                           >
                             OCH 3                                              NO2




                                      ‫ﺗﻘﻞ اﻟﻘﺎﻋﺪﻳﺔ ﺑﺎﺗﺠﺎﻩ اﻟﺴﻬﻢ‬
 
                                                           - ١٢٤ -
   ‫א‬‫א‬                              ١٤٠                                        ‫א‬
      ‫א‬                            ‫א‬‫א‬                         ‫א‬



                                                                    
‫א‬‫א‬‫א‬‫א‬ ‫א‬
                                                     
،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                
،‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
                                            
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                              K‫א‬‫א‬Kb

                                                                           +      _
                      R NH 2 + H2O                                     R NH 3 + OH

                                                                       Alkylammonium ion
                  Amine
                                                         +             _
                                              [ R _ NH3] [ OH ]
                                     Kb =
                                          [ R _ NH2 ]
‫א‬KK‫א‬Kb
                            
                                                    
‫א‬ pKbKb‫א‬‫א‬
                                                                                             
                       W‫א‬‫א‬‫א‬pKb

                        NH2
                                       NH3                        CH3NH2           (CH3)2 NH
      
                             _ 10                    _5                        _4                      _4
          K b = 4.2 * 10            K b = 1.8 * 10                K b= 4.4 * 10         K b= 5.1 * 10
               pK b= 9.38             pK b= 4.74                   pK b= 3.36             pK b= 3.29
                                                                                  
                                                                                                     
               (CH3)3 N
                pK b= 4.26                                                                           
          
                           _
                            10
                                                                                                     
              K b = 5.5 * 10
                                                                                                              
                                                                                                              

                                                   - ١٢٥ -
   ‫א‬‫א‬                                  ١٤٠                                       ‫א‬
       ‫א‬                              ‫א‬‫א‬                         ‫א‬



                                                                                            W‫א‬8-5
                                                                               W‫א‬
                                                                                                            
‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬W
                                                                                               W‫א‬‫א‬
                                                                                                 
                                                W‫א‬‫א‬ J 
                                                                     _
                                                +                 OH
            H3N       + R X                 R NH 3 X                          R NH 2     + H2O + X
                                                                                         o
                       Alkyl halide                                          Primaryamine 1
        
                                                                                             
                                       W‫א‬‫א‬‫א‬ J 
                                                                                   1) CH3Cl
                                                                 CH 3CH 2NH 2                  CH 3CH 2NH
                                                                                   2) OH
                                                                                                        CH 3

                                                                 ‫أﻣﻴﻦ أوﻟﻲ‬                     ‫أﻣﻴ ﻦ ﺛ ﺎﻧﻮي‬
                                                                       o                               o
                                                                    (1)                             (2)
  
               ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                W‫א‬‫א‬‫א‬‫א‬–
‫א‬ ‫א‬K‫א‬‫א‬‫א‬‫א‬‫ א‬K
LIAIH4‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬
                                           
                                                             K‫א‬‫א‬‫א‬
                                                      H2 / Pt
                                  CH3 NO2                                  CH3 NH2

                                 Nitromethane                              Methylamine

                                                             +       _
                                 Fe / HCl                                     Na2CO3
                        NO2                                  NH3Cl                                 NH2


                                                 K‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬K
‫א‬‫א‬،‫א‬‫א‬‫א‬
                                                        
‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬LIAIH4‫א‬
                                                                                               K‫א‬

                                                      - ١٢٦ -
   ‫א‬‫א‬                                ١٤٠                                      ‫א‬
      ‫א‬                              ‫א‬‫א‬                       ‫א‬


                                            H2 / Pd      or
            CH3CH2 C               N                                 CH3 CH2 CH2 NH2
                                           LiAlH4 / Ether

                                        H2 / Pd
                        C      N                                         CH2 NH2

‫א‬‫א‬Hofman degradation‫א‬W
NaOBr‫א‬‫א‬‫א‬‫א‬
  W‫א‬‫א‬E‫א‬‫א‬‫א‬F

                          O
                                                  4NaOH
            CH 3(CH 2)4 C NH 2 + Br2                             CH 3(CH 2)4 NH2 + By Products
                                                   H2O

                                  
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
                                                                             W
                                                            K‫א‬‫א‬‫א‬ J ١
                                                   KNitroalkanes‫א‬‫א‬‫ א‬J ٢
‫א‬‫א‬‫א‬‫א‬ J ٣
‫א‬Nitrobenzene‫א‬‫א‬‫א‬Phenylamine
                 K‫א‬‫א‬‫א‬‫א‬‫א‬




                                                     - ١٢٧ -
   ‫א‬‫א‬                                 ١٤٠                                        ‫א‬
      ‫א‬                               ‫א‬‫א‬                         ‫א‬




                                                                                  W‫א‬8- 6
                                                                W‫א‬‫א‬
                               W‫א‬HCl‫א‬‫א‬‫ א‬J ١
                                                                                  +    _
                          CH3 CH2 NH2 + HCl                               CH3 CH2 NH3 Cl
                                                                                        _
                                                                                     +
                          (CH3)3 N + HCl                                      (CH3)3 NHCl
                                                      WNitrous acid‫א‬‫ א‬J ٢
         ‫א‬–‫א‬‫א‬‫א‬‫א‬ J 
                                                                                                                
                  
         J F‫א‬‫א‬NaNO2 ‫א‬
         ‫א‬‫א‬Diazonium salts‫א‬E٥O
                                                           
         ‫א‬‫א‬،‫א‬‫א‬‫א‬K‫א‬
                                                                     K‫א‬‫א‬‫א‬
                                                                          O
                                                               0-5 C                  +
                               Ph NH2 + HNO2                                      Ph N2

                                                                                Diazonium ion
                                                                                                                
                                                                                                    
                                                                                                            
         ‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬ J 
         ‫א‬‫א‬‫א‬‫א‬‫א‬ENaNO2HCl
                             
         ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬
                                                KEFNitrosoamine
‫א‬‫א‬‫א‬‫א‬
                                                      W‫א‬‫א‬
            CH 3 (CH 2)4 CH 2 NH 2              HNO2
                                                               ‫א‬                  + N2
                      o
                  (1) amine



                                                      - ١٢٨ -
    ‫א‬‫א‬                                     ١٤٠                                                ‫א‬
       ‫א‬                                   ‫א‬‫א‬                               ‫א‬


                       CH3(CH2) NH                                               N=O
                                                                                                          + H2 O
                          o                          HNO2           CH3 CH2-N-CH 2 CH3 + H2O
                          2 amine                                        N-Nitrosodiethylamine
                
                                                     HNO2
                (CH3 CH2)3 N                   No reactions.
    W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ J ٣
                                                     ‫א‬J                  ‫א‬J                ‫א‬J 
                                                                                 W‫א‬‫א‬ K١
                                                           
 ‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                K
                                            NH2                            NH2


                                                      Br2 / H2O


                                                                   Br               Br
                                                                           Br

                                       Aniline                 2,4,6-Tribromoaniline
                                                             
 ‫א‬‫א‬‫א‬
 K‫א‬‫א‬‫א‬‫א‬،
                    NH2                     NHCOCH3                            NHCOCH3                    NH2

                                                                                              +
                           (CH3CO)2O                       Br2                           H2O / H


                                                                                                          Br
                                                                           Br
              Aniline                  Acetanilide               p-Bromoacetanilide                p-Bromoaniline
                                                                                  W‫א‬‫א‬ K٢
                                                                                  
 ‫א‬‫א‬‫א‬‫א‬
                
  ‫א‬‫א‬–N+H3‫א‬‫א‬
                                                               
 p- Nitroaniline‫א‬‫א‬‫א‬
                                
                                                                                                    W‫א‬




                                                           - ١٢٩ -
          ‫א‬‫א‬                                              ١٤٠                                                    ‫א‬
              ‫א‬                                          ‫א‬‫א‬                                     ‫א‬



                         NH2                            NHCOCH 3                            NHCOCH 3                           NH2
                                                                                  O                            +
                                   (CH3CO)2O                       H2SO4/15C                               H2O/H
                                                                       H2 O

                                                                                             NO2                               NO2
                                                                                      P-Nitroacetanilide                P-Nitroaniline
                
                                                                                                                                                    
                                                                                                 W‫א‬‫א‬ K٣
      –‫א‬‫א‬‫א‬‫א‬‫א‬
                                                                                 
                                                                                                         K
                                                                                            _
                                                                              +                                +
                                           NH2                               NH3HSO4                           NH3

                                                                                                    O
                                                        H2SO4                             180-200 C


                                                                                                                    _
                                                                                                               SO3
                                      Aniline                       Anilinium hydrogen
                                                                                                        Sulphanilic acid
                                                                          sulphate

                                                                                                    W‫א‬‫א‬‫א‬٨J ٧
                                                                                                
‫א‬،
      ،‫א‬‫א‬H2N-(CH2)6-H2N"1,6-hexamethylenediamine"
      hexamethylenediamine 
                                                                                             
      ٢٧٠‫א‬C6H12N4W‫א‬‫א‬‫א‬،urotropin
      ،EformaldehydeF‫א‬‫א‬Ko
                                   o٩٥‫א‬E٪٢٧F‫א‬E٪٣٠F‫א‬
      ‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬
      ‫א‬‫א‬،octogen‫א‬hexogen‫א‬
                                                                          
       C6H5-NH2 ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬
      ‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬aniline
      ، ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬

                                                                           - ١٣٠ -
   ‫א‬‫א‬                           ١٤٠                                    ‫א‬
      ‫א‬                         ‫א‬‫א‬                     ‫א‬



                                         
‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬
‫א‬‫א‬،EhydroquinoneF،‫א‬
                                  KE‫א‬F‫א‬‫א‬‫א‬‫א‬
                                                       
‫א‬‫א‬،‫א‬‫א‬
                                                                K،
                                                                                                       
                                                                                                       
                                                                                                       




                                                - ١٣١ -
   ‫א‬‫א‬                                ١٤٠                                           ‫א‬
      ‫א‬                              ‫א‬‫א‬                           ‫א‬



                                     E‫א‬‫א‬F
                                                                          W‫א‬‫א‬‫ א‬K١
            1) CH3 CH2 N(CH3)2                              2) CH3 CH2 CH CH3
                                                                                 NH2

                              +      _                      4) CH3 CH CH2 CH2CH2
            3)        CH3 CH2 N(CH3)3I
                                                                           Br              NH2


            5)                      NH2                     6)                       CH CH2 CH2
                                                                                     NH2    OH
                               Br
                                                                  W‫א‬‫א‬‫ א‬K٢
            1) Cyclopentylamine .                          2) B-phenylethylamine .
            3) 1,6-Hexamethylendiamine .                   4) Benzylamine .
            5) N,N-Dimethylamine .                         6)tetra-n-Butylammonium
                                                           iodide .
            7) P-Aminobenzoic acid .
 K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٣
            1)        CH3 CH2 CH NH2                                                   _
                                                                           +
                                                            2)      (CH3)3 NHNO3
                              CH3

                                                            4)      (CH3CH2) C NH2
            3)               NH


                                       _
                             +
            5)               N(CH3)2 Cl                     6)                   NCH3

                                                                                                 _
                                                                                     +
            7)                 N(CH3)2                      8)           (CH3)2 CH N (CH3)3 Br


                              K‫؟‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٤
                                            W‫א‬‫א‬ K٥

                      O2 N          NH 2
                                              ,   CH 3O                   NH 2   ,               NH 2   (A
               
                                                     - ١٣٢ -
 ‫א‬‫א‬                                ١٤٠                                         ‫א‬
    ‫א‬                              ‫א‬‫א‬                          ‫א‬


                                                                                         O

                             NH3
                                     ,        (CH3)2 NH       ,   (CH3)3 N      ,   CH3-C-NH 2        (B
                                                                                 W‫א‬‫א‬ K٦
                                         1) CH3Cl
           a)       (CH 3CH 2)2 NH
                                         2)    OH
                                                                            ?

                    Br                                  Br
                                     ?
          b)
                         NO2                                      NH2
                                          H2 / Pt
          c)         CH3CH2CN                                               ?
                            O
           d) CH3CH2 C NH2 + Br2
                                                          4NaOH
                                                                            ?
                                                           H2O

                                                                        +           _
          e) CH3NH2 +            ?                                CH3 NH3Cl

          f)        (CH 3CH2)2 N CH 3
                                                HNO2
                                                                            ?
                     NH 2                                               NH 2
                                                                  Br                Br
          g)
                            +    ?
                                                                        Br


          h)                NH2 + CH3Cl                                     ?
                                                                                                               
                                                                                                               
                                                                                                               




                                                    - ١٣٣ -
 ‫א‬‫א‬                             ١٤٠                                        ‫א‬
    ‫א‬                           ‫א‬‫א‬                        ‫א‬



                               E‫א‬‫א‬F
                                                                                      WE1F‫א‬‫א‬
          1) Ethyl dimethyl amine .             4) 1-Amino-4-bromo pentane .
          5) O- bromo aniline .
                                                                                      WE٢F‫א‬‫א‬
                            CH 2NH 2
                                                (4                                   NH 2      (1
                                                                      
                    
                                                                                    +
                                                                                         _
                                                             (CH 3CH 2CH 2CH2)4 N I            (6
                                                      
                                                                                      WE٣F‫א‬‫א‬
                               KE3                              KE2
                               KE6                                     KE4
                                                                                      WE٥F‫א‬‫א‬
                                   P-methoxy aniline > Aniline > P-Nitro aniline .
                                                                  WE٦F‫א‬‫א‬
                        CH3CH 2CH2 NH2 (c                           (CH 3CH 2)2 N CH 3         (a
                             K (f                                         HCl      (e
                                                                                                          
                                                                                                          




                                                   - ١٣٤ -
       ‫א‬‫א‬                                    ١٤٠                                    ‫א‬
                                         ‫א‬‫א‬                    ‫א‬



                                             ‫א‬‫א‬
                                                                              W‫א‬‫א‬‫א‬
‫א‬W‫א‬،‫א‬‫א‬‫א‬K‫א‬‫א‬، K١
                                                          
                                                                                 ١٩٨٩
      ‫א‬W‫א‬،‫א‬‫א‬K،‫א‬،‫ א‬K٢
                                                                                 ١٩٩٠
       ١٩٩٦،‫א‬،‫א‬،‫א‬‫א‬K،‫ א‬K٣
١٩٩٨،‫א‬،‫א‬،‫א‬K‫א‬، K٤
  ،‫א‬‫א‬‫א‬K،‫א‬‫א‬،‫א‬،‫ א‬K٥
                                                               ٢٠٠٠،‫א‬،‫א‬



                                                                             W‫א‬‫א‬‫א‬W
1.Fessenden, Ralph J.and Fessenden, Joan S. Organic Chemistry ,2nd ed, PWS, Boston
1982.




                                                 - ١٣٥ -
‫א‬                                               ١٤٠                                                  ‫א‬
                                               ‫א‬‫א‬                                  ‫א‬



                                                 ‫א‬
   ‫א‬                                                                                                
                  ١–‫א‬‫א‬
          ٢‫א‬     ١J ١
     ٣‫א‬‫א‬               ١J ٢
     ٥‫א‬‫א‬‫א‬                 ١J ٣
     ٨               ١J ٤
                     ١٠‫א‬–‫א‬‫א‬
    ١١‫א‬                ٢J ١
    ١١‫א‬                   ٢J ٢
    ١٨‫א‬‫א‬‫א‬                      ٢J ٢J ٢
    ١٨‫א‬‫א‬‫א‬                         ٢J ٢J ٣
    ٢٢‫א‬                          ٢J ٢J ٤
    ٢٣‫א‬                   ٢J ٣
     ٢٣‫א‬                ٢J ٣J ١
    ٢٧‫א‬‫א‬‫א‬                       ٢J ٣J ٢
    ٢٧‫א‬                       ٢J ٣J ٣
    ٣١‫א‬                   ٢J ٣J ٤
     ٣٢‫א‬                   ٢J ٤
     ٣٢‫א‬                ٢J ٤J ١
     ٣٢‫א‬‫א‬‫א‬                      ٢J ٤J ٢
    ٣٤‫א‬                    ٢J ٤J ٣
    ٣٦‫א‬                   ٢J ٤J ٤
     ٣٨‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬                           ٢J ٤J ٥
    ٣٩                     ٢J ٥
‫א‬                                           ١٤٠                                          ‫א‬
                                           ‫א‬‫א‬                          ‫א‬




                  ٤٢‫א‬‫א‬–‫א‬‫א‬
    ٤٣‫א‬    ٣J ١
    ٤٣‫א‬         ٣J ٢
    ٤٤‫א‬‫א‬          ٣J ٣
    ٤٥‫א‬‫א‬‫א‬            ٣J ٤
    ٤٦‫א‬           ٣J ٥
     ٤٩‫א‬‫א‬               ٣J ٦
     ٥٠‫א‬‫א‬                ٣J ٧
  ٥٦      ٣J ٨
                  ٥٩‫א‬‫א‬‫א‬–‫א‬‫א‬‫א‬
     ٦٠‫א‬    ٤J ١
     ٦٠‫א‬‫א‬‫א‬                     ٤J ٢
     ٦١‫א‬‫א‬‫א‬         ٤J ٣
    ٦٢‫א‬‫א‬‫א‬                        ٤J ٤
    ٦٣‫א‬‫א‬‫א‬                    ٤J ٥
     ٦٥‫א‬‫א‬‫א‬           ٤J ٦
     ٦٦         ٤J ٧
                  ٦٩‫א‬‫א‬J ‫א‬‫א‬
      ٧٠‫א‬    ٥J ١
   ٧٠‫א‬            ٥J ٢
   ٧١‫א‬          ٥J ٣
   ٧٣‫א‬      ٥J ٤
     ٧٤‫א‬‫א‬‫א‬‫א‬                    ٥J ٥
    ٧٥‫א‬‫א‬                  ٥J ٦
    ٧٧‫א‬‫א‬                 ٥J ٧
    ٨٠       ٥J ٨
‫א‬                                           ١٤٠                                           ‫א‬
                                           ‫א‬‫א‬                           ‫א‬




                   ٨٣‫א‬‫א‬–‫א‬‫א‬
      ٨٤‫א‬    ٦J ١
      ٨٤‫א‬‫א‬        ٦J ٢
      ٨٦‫א‬‫א‬‫א‬                ٦J ٣
      ٨٧‫א‬‫א‬               ٦J ٤
       ٨٨‫א‬‫א‬          ٦J ٥
      ٨٩          ٦J ٦
           ٩٢‫א‬‫א‬‫א‬–‫א‬‫א‬
       ٩٣‫א‬    ٧J ١
       ٩٣‫א‬‫א‬‫א‬                 ٧J ٢
      ٩٦‫א‬‫א‬‫א‬                        ٧J ٣
       ٩٧‫א‬‫א‬‫א‬                   ٧J ٤
     ١٠٠          ٧J ٥
          ١٠٢‫א‬‫א‬–‫א‬‫א‬
     ١٠٣‫א‬     ٨J ١
     ١٠٣‫א‬‫א‬                      ٨J ٢
     ١٠٦‫א‬‫א‬‫א‬‫א‬‫א‬                           ٨J ٣
    ١٠٨‫א‬‫א‬                         ٨J ٤
      ١١٠‫א‬‫א‬                        ٨J ٥
      ١١٠‫א‬‫א‬                        ٨J ٦
      ١١١‫א‬‫א‬                          ٨J ٦J ١
      ١١٣‫א‬‫א‬‫א‬‫א‬‫א‬                               ٨J ٦J ٢
      ١١٤‫א‬‫א‬                             ٨J ٦J ٣
      ١١٥          ٨J ٧
‫א‬                                           ١٤٠                                         ‫א‬
                                           ‫א‬‫א‬                         ‫א‬




                   ١١٩‫א‬–‫א‬‫א‬
       ١٢٠‫א‬    ٩J ١
       ١٢٠‫א‬              ٩J ٢
       ١٢٣‫א‬‫א‬‫א‬              ٩J ٣
       ١٢٤‫א‬        ٩J ٤
       ١٢٦‫א‬           ٩J ٥
  ١٢٨‫א‬       ٩J ٦
       ١٣٠‫א‬‫א‬‫א‬              ٩J ٧
       ١٣٢         ٩J ٨
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              ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬

            ‫א‬E‫א‬F‫א‬‫א‬

GOTEVOT appreciates the financial support provided by BAE SYSTEMS

								
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