Organic Chem Wkst

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					Unit 10 Organic Chemistry (4/09)                                                                         3. Make a table similar to the one below to record the information about each
                                                                                                            molecule.
1. Draw the following molecules.                                                                                                                           Shape of the molecule at
   a) 2-butanol                            b) 3-pentanone                                                     Molecule’s Lewis                                     this atom.
                                                                                                                                    atom    Bond angle
   c) hexanal                              d) propanoic acid                                                     Structure                                   (Tetrahedral, trigonal
   e) 2,2-dimethylpentanal                 f) dibutyl ether                                                                                                      pryamid, etc.)
   g) butylmethanoate                      h) 2-pentyne                                                      methanoic acid
   i) cyclohexane                          j) ethylmethylamine
   k) 2,3-dimethylpentane                  l) 2-butene                                                       methylamine
   m) 3,3-dimethyl-1-hexyne                n) 3-methyl-2-hexanol
   o) 3,3 diethyl-4-propyl-2,4,5-trimethyloctane
                                                                                                             BF3
   p) propanoic acid                       q) ethylmethanoate
   r) dipropylamine                        s) ethylpropylether                                               ClF5
   t) 2-butanone                           u) propanal
     v) trans-2-pentene                                             w) methylethanoate                   4. Consider the following chemicals, methane, methanol, methanoic acid, and
                                                                                                            methanal.
2. Name the following structures according to IUPAC rules.                                                  a) Which of these undergo H-bonding?
            H2                             CH3                                                              b) Which of these has the greatest Van der Waal forces?
            C         OH                                             H2       H2
     H3C         C                         C                         C        C                             c) Which of these is non-polar?
                 H2                 H2C         CH3           H3C         O        CH3
a)                             b)                        c)                                                 d) Which one should have the lowest boiling temperature and which one
                                                                                                               should have the highest?
                                                        H2   H2
                                                        C H C                                            5. Complete the following reactions by identifying the product(s).
                                                    H3C    C    CH3                       H3C
            H2        H2             CH3
                                                         H2C                        H3C
                                                                                              C
                                                                                                   CH3      a) CH4 + Cl2   
                                                                                                                            uv
                                                                                                                                          b) CH3CH3 + Br2     
                                                                                                                                                                uv
                                                                                                                                                                   
            C         C        HC
     H3C         C         C                                    CH2                       C
                                     CH3                                           H3C            CH3
                 H2                                                                                      6. Show the mechanism as ethane reacts with bromine gas.
                           O                                 H3C                          CH3
d)                                             e)                             f)
                                                                                                         7. Complete the following reactions by identifying the product(s).
            H2 H2
                                           H2 H2                          H2 H2                                     H                                  H
            C C                                                                                                     C                                   C
                                           C C                            C C         H2
                                                                                                              HC       CH2       +
                                                                                                                               Br2
                                                                                                                                                  HC       CH2 + HCl
      H3C             C    H         H3C            C   OH          H3C        C    O C CH                  a) 3                              b) 3
                                                                                          3

g)
                      O
                                h)                  O
                                                               i)              O
                                                                                                            c)
                                                                                                                 H2C   CH2   +   Cl2
                                                                                                                                              d)
                                                                                                                                                   H2C   CH2   +   H2O


                                                                                                         8. Consider the following chemicals, n-butane and 2-methylpropane, explain why
                                                                                                            n-butane has a higher boiling temperature.

                                                                                                         9. Consider ethanol and dimethylether, explain why ethanol has a higher boiling
                                                                                                            temperature then diethyl ether.
10. Complete the following reactions by identifying the product(s).           18. Use 2-chloro-2-methylpropane to demonstrate a SN1 substitution reaction
                 O                                                                with NH3. Show curly arrows.
          H3C    C        +   KOH
                                                H3C
                                                      NH2
                                                            + HCl
     a)              OH                    b)                                 19. Use 2-chloropropane to demonstrate a SN2 substitution reaction with OH-.
                                                                                  Show the curly arrows.
     c) CH3CH2COOH + NaOH                 d) (CH3)2NH + HNO3 
                                                                              20. Use 1 chloropropane to demonstrate a SN1 substitution reaction with KCN.
                                                                                  Show curly arrows
11. Complete the following reactions by identifying the product(s).
           CH3
                          K 2Cr2O 7                                           21. Explain the difference between an addition polymer and a condensation
                                                      H2          K 2Cr2O7
          HC    C OH
                                                      C                           polymer.
                H2
           CH3                                  H3C        OH
     a)                                    b)                                 22. Write a reaction showing the addition reaction between 3 molecules of
                                                                                  ethene to make polyethylene.
               OH                                 O
                           K 2Cr2O7                             K2Cr2O7       23. Write a reaction showing the addition reaction between 3 molecules of 2-
     H3C       C CH3                           C CH
               H                           H3C     3                              butene to make polybutene.
c)                                    d)
                                                                              24. Draw a short section of polypropylene.
12. Write and name the sequential products when the following are oxidized
    using K2Cr2O7:                                                            25. Draw a short section of poly styrene which is composed of the monomer,
    a) 1-propanol                                                                 phenylethene.
    b) 2-butanol
                                                                              26. Write a reaction showing the products formed
    c) methyl-2-propanol
                                                                                  a) as ethene reacts with HCl
13. Write and name the sequential products when the following are oxidized        b) as propane reacts chlorine in the presence of UV.
    using K2Cr2O7:                                                                c) as ethanoic acid reacts with methyl amine
    a) ethanal                                                                    d) as methylbromide reacts with CN-
    b) propanone                                                                  e) as methyl amine reacts with ethanoic acid with.
14. Write and name the sequential products when the following are oxidized
    using K2Cr2O7:                                                            27. Complete the following reactions and name the products.
    a) 2-propanol                                                                 a) CH3COOH + H3CCH2OH 
    b) methanol                                                                   b) methylamine + propanoic acid 
    c) 2-methyl-2-butanol                                                         c) 2-butanol + methanoic acid.
15. Write and name the sequential products when the following are oxidized
                                                                              28. Consider the molecule 2-methylpentane. Write chemical reactions showing
    using K2Cr2O7:
                                                                                  the substitution reaction with Cl2 that produces
    a) ethanal
                                                                                  a) a primary chloroalkane
    b) propanone
                                                                                  b) a secondary chloroalkane
16. Consider the molecule 2-methylbutane. Write a chemical reaction showing       c) a tertiary chloroalkane
    the substitution reaction of Br2 that produces:
    a) a primary bromoalkane
    b) a secondary bromoalkane
    c) a tertiary bromalkane

17. Use chloromethane to demonstrate a SN2 substitution reaction with CN-.
    Show the curly arrows.
28. Write a reaction showing how the following react.           33. Write a chemical reaction showing how the addition of H2, Br2, HBr and
    a) CH3Br + CN-                                                 H2O reacts with
    b) 2-butene + Br2                                             a) ethene              b) 2-butene
                  K2Cr O7
    c) butanal    2
                       
                   K2Cr O7                                      34. Write a chemical reaction showing the polymerization of
    d) 2-propanol  2
                           
                                                                    a) ethene            b) 2-butene               c) chloroethene
    e) Ethane + Br2    
                        uv
                           
    f) propanoic acid + dimethylamine                          35. Write a chemical reaction showing the oxidation using K2Cr2O7 on
                                                                   a) propanal            b) propanone
    g) dimethylamine + ethanoic acid 
    h) methanoic acid + sodium hydroxide                       36. Write a chemical reaction showing the reaction between
                                                                    a) propanoic acid and NaOH             b) ethanoic acid and methylamine
29. Show the mechanism when OH- reacts with
                                                                37. Describe the intermolecular forces and predict if the 3 carbon member of
    a) 1-bromopropane.
                                                                    the following families are water soluble.
    b) 3-chloro-3-ethylpentane
                                                                    a) alkanes
                                                                    b) alcohols
30. Write a reaction showing the mechanism as OH- reacts with
                                                                    c) ketones
    a) 1-bromopropane
                                                                    d) amines
    b) 2-bromo-2-methyl butane
                                                                    e) ethers
31. Write a reaction showing the products formed
                                                                38 Describe how the boiling temperature should change as you increase the
    a) as ethene reacts with HCl                                   molar mass of a homologous series.
    b) as propane reacts chlorine                               39. Draw and name the 3 carbon member of each of the following functional
                                                                    groups: alkane, alkene, alkyne, aldehyde, ketone, carboxylic acid, alcohol,
    c) as ethanoic acid reacts with methyl amine
                                                                    amide, amine, esters, and halogenoalkane.
    d) as methylbromide reacts with CN-
                                                                40. Draw and name the 4 carbon straight chain member of each of the
    e) as methyl amine reacts with ethanoic.                        following functional groups: alkane, alkene, alkyne, aldehyde, ketone,
                                                                    carboxylic acid, alcohol, amide, amine, esters, and halogenoalkane.
32. Write a reaction showing how the following react.
    a) CH3CH2Br + CN- 
    b) propene + Br2 
                   K2Cr O7
    c) butanone    2
                           
                     K2Cr O7
    d) 1-propanol    2
                             
    e) propane + Cl2   
                        uv
                           
    f) ethanoic acid + methylethylamine 

    g) HNO3 + ethylamine 
    h) ethanoic acid + lithium hydroxide 

				
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