Chem 335 - Winter 2000
Organic Chemistry II
Dr. Carl C. Wamser

Chapter 16 Homework

Brown & Foote, pages 623 - 629 :
Problems 16.7 - 13 , 15 - 25 , 27 , 28 , 30 - 40

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.