Chem 336 - Spring 2002
Organic Chemistry III
Dr. Carl C. Wamser
Carey, pages 822 - 830:
Problems 20.25 - 20.45
1. Write complete names for each of the following:
a) 
4-oxo-5-phenylpentanenitrile
(S)-4-bromo-N-propylpentanamide
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
c) butyl butanoate
d) butanamide
e) pentanoic acid
