Organic Chemistry III

Professor Carl C. Wamser

Homework 20 Answer Key

Chem 336 - Spring 2005

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