Chemistry 332 - Spring 1996
Elements of Organic Chemistry II
Homework, Chapter 10 - Carboxyl Derivatives
McMurry, pp 320-324:
Problems 10.31-34, 36-41, 44, 46, 49, 53, 54, 57, 61
1. Write complete names for each of the following:
a) 
5-phenyl-4-oxopentanenitrile
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.
See also the structure in the notes, which has C12 fatty acids.
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
