Carroll, pp 312 - 315: # 3 , 4 , 5 , 6 , 7 , 8 , 9 , 11 , 12 , 15 , 16 , 18 , 20
1. The reaction below is a nucleophilic substitution that involves substantial carbocation rearrangements. Illustrate how the various products are formed.
2. Propose a mechanism for the following substitution that explains the retention of configuration.
3. The Wolff rearrangement, shown below, is considered to proceed through a ketene intermediate. Write a complete mechanism.
Expand the mechanism by taking into account gas-phase work that showed that if the original carbonyl carbon is labeled, the label may appear in either of the two (nonmethyl) carbons of the ketene.
