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					Chemistry 102            Name --------------------------------------------------------------

Examination No. 2        ID#----------------------------------------------------------------

100 Points




PART I:      TRUE OR FALSE - 15 QUESTIONS - 2 POINTS EACH - 30 POINTS
                                                                                               2
      Circle either TRUE / FALSE:

1.     T     F      Dehydration (intermolecular) of 2-butanol will form di-sec-butyl ether..



2.     T     F
                                      OH


                                            is a phenolic compound.



3.     T     F      p-methylbenzaldehyde will not give a positive Fehling's Test.

4.     T     F      tert-butyl alcohol is the same as 2-methyl-2-propanol.

5.     T     F      A saturated carboxylic acid of 13 carbons is considered to be a Fatty
                    Acid.

6.     T     F      Alfred Nobel discovered Nitroglycerine.

7.     T     F      3-methyl-2-hexenoic acid is largely responsible for "body odor".
                    This acid is capable of forming cis/trans Geometric Isomers.

8.     T     F      sodium benzoate is soluble in water.

9.     T     F      When Chromic Acid, H2CrO4 reacts with an aldehyde, the aldehyde acts
                    as a reducing agent.

10.    T     F      Glucose-6-Diphosphate has two high energy phosphate ester bonds.

11.    T     F      2-methyl-2-hexanol has eight (8) beta () hydrogen atoms.

12.    T     F      2-pentanol will give a positive Iodoform Test..

13.    T     F      Oxidation of a thioalcohol will form a disulfide bond or bridge.

14.    T     F      Alcohols, carboxlic acids ands esters are associated liquids.

15.    T     F      In an aqueous solution of Glucose, there is a dynamic equilibrium
                    among the ,  and open-forms. The Reducing Sugar is the 
                    form.




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PART II - MULTIPLE CHOICE - 10 QUESTIONS - 3 POINTS EACH - 30 POINTS

1.   Which of the following alcohols is named incorrectly?

     A.    4-penten-2-ol
     B.    2-methyl-3-butanol
     C.    isobutyl alcohol
     D.    sec-butyl alcohol
     E.    1-pentyn-3-ol
     F.    no answer shown

2.   Which of the following would not undergo mild oxidation to form an aldehyde?

     A.    2-methyl-1-propanol
     B.    isopentyl alcohol
     C.    1-butanol
     D.    cyclohexanol
     E.    no answer shown

3.   Which of the following alcohols would undergo strong oxidation to produce a ketone?

     A.    4-methyl-1-pentanol
     B.    3-methyl-2-hexanol
     C.    3-phenyl-3-hexanol
     D.    isohexyl alcohol
     E.    no answer shown

4.   Which of the following organic compounds has the highest boiling point?
     (All compounds listed have approximately the same molecular weight)

     A.    methyl n-butyl ether
     B.    1-pentanol
     C.    ethyl n-propyl ether
     D.    n-hexane
     E.    1-hexene




                                                                                           3
                                                                                       4
5.   The following compound is Vanillin:
                                                 O
                                                 CH




                                                       OCH 3
                                                 OH


     Which statement about Vanillin is false?

     A.     it   is a secondary Alcohol
     B.     it   has an Ether functional group
     C.     it   would give a positive Tollen's Test
     D.     it   would react with an aqueous solution of sodium hydroxide
     E.     it   is Aromatic

6.   Strong oxidation of 3-methyl-1-hexanol would yield:

     A.     -methylcaproic acid
     B.     2-methylhexanoic acid
     C.     -methylcaproic acid
     D.     -methylcaproic acid
     E.      no answer shown

7.   The product of the reduction of 3-isopropylcyclohexanone is :

     A.     3-isopropylcyclohexanol
     B.     3-isopropylcyclohexanaldehyde
     C.     cyclohexanol
     D.     1,3-cyclohexanediol
     E.     no answer shown

8.   What is the major organic product formed from the acid-catalyzed intramolecular
     dehydration of 1-methylcyclohexanol?

     A.     methylcyclohexane
     B.     methlenecyclohexane
     C.     3-methylcyclohexene
     D.     2-methylcyclohexene
     E.     1-methylcyclohexene




                                                                                       4
                                                                                                 5

9.    Which compound with not give a positive Chromic Acid (H2CrO4) test?

      A.     1-hexanol
      B.     2-hexanol
      C.     hexanal
      D.     2-methyl-2-hexanol
      E.     benzaldehyde

10.   Which compounds would be used in the Fischer Esterification to form isopentyl butanoate?



      A.     3-methyl-1-butanol, butanoic acid, sulfuric acid
      B.     2-methyl-1-butanol, butanoic acid, sulfuric acid
      C.     3-methyl-1-pentanol, butanoic acid, sulfuric acid
      D.     3-methylbutanoic acid, 1-pentanol, sulfuric acid
      E.     no answer shown

PART III - NOMENCLATURE - 4 QUESTIONS                   3 POINTS EACH           12 POINTS

Draw structural formulas for each of the following:

A.    Ibuprofen: 2-(p-isobutylphenyl)propanoic acid..




B     Aspirin (Acetylsalicyclic Acid)




C.    any Neutral Fat or Triglyceride




D.    Allose-4-Phosphate: ( a Phosphate Ester)
                                                      OH
                                                 O                                               5
                                                                                              6




                                                 ALLOSE




PART IV - 28 POINTS               Draw the structural formula for the major organic product
formed by each of the following organic reactions: All reactions take place as written:



a.

                COONa
                                  H 2O
                      + HCl
                              "Neutralization"
                COONa


                                                                     ANSWER




b.
              COOH
                                         H 2O
                     + NaHCO3

              COOCH 2CH 2CH 3


                                                                     ANSWER




c.
             O
                          H 2O                                                                6
            O    + NaOH
                      "Saponification"
                                                                                7




                                                                      ANSWER



d.                O
                                                 H 2SO4
     CH 3CH 2CH 2COCH 2CH 2CHCH 3 + H 2O                   2 Organic Products




                      ANSWER                                  ANSWER

e.
                  O
                                    Acid
                       +   H 2O                  2 Organic Products
              O                   "Hydrolysis"




                      ANSWER                                  ANSWER




                                                                                7
                                           8

f.

         Acid
                     a Cyclic Hemiacetal



     O          OH




          ANSWER




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