Organic Chemistry III

Professor Carl C. Wamser

Chem 336 - Spring Term

Chapter 19 Homework Answers

1. Write complete names for each of the following:



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