Organic Chemistry III
	Professor Carl C. Wamser
Chem 336 - Spring 2009	Chapter 19 Homework Answers

Carey, pages 855 - 861

Problems 19.13 - 27 , 31 - 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.

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 is likely to be slow and may be complicated by some elimination.