McMurry, pp 375-377:
Problems 12.24-30, 32, 38-40, 50
1. Write all the resonance forms for protonated imidazole. One is shown below.
Note that you cannot locate the positive charge on the other two carbons correctly.
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) 
favorable to the right (alkyl amines are stronger bases than aryl amines)
b) 
favorable to the left (the pKa for arylammonium ions is less than 7)
c) 
favorable to the right (the pKa for alkylammonium ions is greater than 7)
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.
