Chem 335 - Winter 1999 - Organic Chemistry II
Portland State University - Dr. Carl C. Wamser

Chapter 17 Homework

Brown & Foote, pages 674 - 685 :
Problems 17.13 - 23 , 25 - 37 , 40 - 42 , 48

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