Chem 336 - Spring 2004
	Organic Chemistry III
	Professor Carl C. Wamser

Homework Answers, Chapter 20

Carey, pages 877 - 885

Problems 20.24 - 28 , 31 , 32 , 34 - 38 , 40 - 44

1. Write complete names for each of the following:

a)

4-oxo-5-phenylpentanenitrile

b)

(S)-4-bromo-N-propylpentanamide

c)
isopropyl cyclopentanecarboxylate

2. A typical protein linkage is an amide bond (also called a peptide bond), such as might be found in N-methylacetamide. Proteins are typically hydrolyzed in strong acid. Write a complete mechanism for the acid-catalyzed hydrolysis of N-methylacetamide.

3. A typical fat has ester functional groups (most typically it is a triester between three fatty acids and glycerol). Glycerol is 1,2,3-propanetriol, and a fatty acid might be decanoic acid. Write the structure for the triester made from these components.

4. Using butanoic acid as the only organic starting material, show how to prepare:

a) 1-butanol

b) 1-bromobutane

c) butyl butanoate

d) butanamide

e) pentanoic acid