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Aromatics

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					 What do aspirin, Tylenol, ibuprofen, almonds,
  vanilla, and mothballs have in common?
                                      O
                     OH
 O                                                               O        H
                                          OH   O      H
      O    OH

                O
                    HN     O                                O
                                                                     OH
                         CH3


     aspirin        Tylenol    ibuprofen       almonds          vanilla       mothballs
                                                     Structural Properties:
Aromatic ring
                                                             Planar
                                                   All C atoms sp2 hybridized
                                                   All C-C bonds equal length

                                                      electrons
                                                   “smeared out”
               Resonance structures
                                             Structure of Benzene



                                                                   H           H
                                                                       C   C

                                                      H C                      C H

                                                                   C       C
                                                                   H       H
Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212
                                                                   Benzene


            3-D
              – VSEPR Diagram




Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212
                Aromatic Compounds
                                   CH3                      OH
            Benzene, C6H6

                                          Toluene                 Phenol
   Chemical Properties
Special Stability (aromaticity)                   NH2
   No addition reactions
          Hf                                           Aniline

      -156 kJ/mol
                    + 118 kJ/mol     Aromatic substituents:
      -38 kJ/mol                         phenyl
                    + 113 kJ/mol
       75 kJ/mol
                    - 26 kJ/mol          benzyl
       49 kJ/mol
Benzene
    • C6H6
    • Uses: styrene; phenol;
      synthetic detergents;
      cyclohexane for nylon;
      DDT; insecticides;
      fumigants; solvent; paint
      removers; rubber cement;
      antiknock gasoline
                             Cl           CH3
   Names of
monosubstituted
 benzene rings
                        Chlorobenzene   Toluene


     Br          OH           NO2          CH=CH2




Bromobenzene   Phenol   Nitrobenzene    Styrene
                                       OH

Phenol, (carbolic acid)
            • C6H5OH
            • Uses: solvent for refining
              lubricating oils; salicylic
              acid; phenoltpthalein;
              germicidal paints;
              pharmaceuticals;
              laboratory reagent;
              slimicide
                              Benzene        NO3-   Nitrobenzene




Mark Wirtz, Edward Ehrat, David L. Cedeno*
     Aromatic
   Hydrocarbons




Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 430
Cholesterol
Compounds
                    CH3
    6


    C       C   1




C
5
                    C ortho
                      2




    C   4
            C   3


para                meta

                position number     name
                      1, 2        ortho- (o-)
                      1,3         meta- (m-)
                      1,4         para- (p-)
      H                   CH3
          6


          C       C   1




H C
 5
                          C CH3
                            2




          C   4
                  C   3




      H               H
 ortho-dimethylbenzene
            or
 1, 2 - dimethylbenzene
      H                   CH3
          6


          C       C   1




H C
 5
                          C H
                            2




          C   4
                  C   3




      H               CH3
 meta-dimethylbenzene
            or
 1, 3 - dimethylbenzene
      H                   CH3
          6


          C       C   1




H C
 5
                          C H
                            2




          C   4
                  C   3




      CH3             H
 para-dimethylbenzene
            or
 1, 4 - dimethylbenzene
      H                   MD
          6


          C       C   1




H C
 5
                          C H
                           2




          C   4
                  C   3




      MD              H
          para-docs
              or
           paradox
      H                   MD
           6


          C       C   1




H C
 5
                          C MD
                           2




          C   4
                  C   3




      H               H
          ortho-docs
               or
           orthodox
         Fe2+             Fe2+
            6


          C       C   1




Fe2+ C
    5
                           C Fe2+
                            2




          C   4
                  C   3




         Fe2+         Fe2+
          ferrous wheel
                 or
           ferris wheel
      H            NO2
          C    C

H C                    C NO2

          C    C
      H            H
   o - dinitrobenzene
             or
  1, 2 - dinitrobenzene
                                CH3
         CH3          NO2
             C    C

O 2N C                 C H
                              Toluene
          C       C
         H            NO2
    2,4,6 - trinitrotoluene
               or
              TNT
                                       CH3
                                O2 N         NO2

2,4,6 -Trinitrotoluene
                                       NO2




           • CH3C6H2(NO2) 3
           • Uses: Explosives;
             intermediate in dyestuffs
             and photographic
             chemicals
           • Will detonate only if
             vigorously shocked or
             heated to 450oF
                                    CH3
       Cl             CH3
         C       C

H C                       C Cl
                                  Toluene
         C        C
       Cl             H
    2, 4, 6 - trichlorotoluene
                  or
2, 4, 6 -trichloromethylbenzene
                            O
       H               O C CH3
           C       C

H C                        C COOH

           C       C
       H               H
   2-acetyloxybenzoic acid
                or
(acetylsalicylic acid or aspirin)
       H             H                H           H
           C     C                        C   C
                           H
Cl C                  C C         C                   C   Cl
                         CCl3
                      Cl C Cl
           C      C            C              C
                         Cl
       H            H         H                   H
dichlorodiphenyltrichloroethane
              or
             DDT
      H            CH CH2
          C    C

H C                    C H

          C    C
      H            H
                                n
       phenyl ethene
             or
      polystyrene a.k.a. (styrofoam)

				
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