Organic Chemistry 302

Final Examination – May 5, 1999

I. (Five points each) Synthesize the following:

II. (Three points each) Complete the following reactions:

a. ethanoic acid + LAH ®

b. benzoyl chloride + propanoic acid ®

c. N-methylacetamide + NaOH/H₂O ®

d. methyl butyrate + H₂¹⁸O/H⁺ ®

e. phenyl benzoate + SOCl₂ ®

f. benzamide + ethanol ®

g. acetone + N-methylamine ®

h. benzoic acid + NaBH₄ ®

i. propionic anhydride + methanol ®

III. (Three points each) Complete the following, give the product(s) and mechanism.

IV. (Four points each)

a. Can the following compound be made via a Diels-Alder reaction? Explain.

b. Which of the following would be the stronger carboxylic acid? Explain.

3-aminobutanoic acid 3-nitrobutanoic acid butanoic acid

c. Why does nucleophilic aromatic substitution have more specific requirements in order to occur than does electrophilic aromatic substitution?

V. (Five points each) Give a complete mechanism for the following:

a. methyl ethanoate + ammonia ® ethanamide + methanol

b. ethyl acetate + sodium ethoxide ®

excess sodium ethoxide/CH₃Br