Chem 336 - Spring 1999 - Organic Chemistry III
Portland State University - Dr. Carl C. Wamser

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Chapter 21 Homework

Brown & Foote, pages 874 - 882:
Problems 21.15 - 25 , 28 - 32 , 34 , 45 , 46

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.