Chem 336 - Spring 2002
Organic Chemistry III
Dr. Carl C. Wamser

Chapter 22 Homework

Carey, pages 907 - 916:
Problems 22.21 - 22.49


1. Write all the resonance forms for protonated imidazole. One is shown below.

2. Predict whether the following acid-base equilibria would be more favorable to the right or to the left. Use pKa data from your text.

a)

b)

c)

3. Given an optically active sample of 1-amino-1-phenylethane, write a series of reactions that could be used to resolve a racemic mixture of 2-methylbutanoic acid.