Organic Chemistry III

Professor Carl C. Wamser

Homework, Chapter 22

Carey, pages 962 - 970 :

Problems 22.21 - 26 , 28 - 40 , 42 - 47

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.