Chem 336 - Spring 2002
Organic Chemistry III
Dr. Carl C. Wamser

Chapter 19 Homework Answers

Carey, pages 768 - 773:
Problems 19.13 - 19.34

1. Give IUPAC names for the following:

a)

(1S,2R)-2-methylcyclopentanecarboxylic acid

Note - (cis) is correct but not specific enough to identify this enantiomer

b)

(E)-5-methyl-3-oxo-4-heptenoic acid

(trans) would also be acceptable

2. Write a complete mechanism for the acid-catalyzed hydrolysis of methyl acetate.
The mechanism is the exact reverse of Fischer esterification.

Note the beautiful symmetry of this mechanism.

3. Show two different ways to prepare cyclohexanecarboxylic acid starting with cyclohexane.

The upper pathway is likely to be better because the SN2 displacement by CN- on the 2° alkyl bromide may be complicated by some elimination.