Chapter 15: Problem 6
The synthesis of toluene by the aluminum chloride-catalyzed Friedel-Crafts alkylation of benzene with methyl chloride is badly complicated by the formation of dimethylated, trimethylated, and polymethylated benzenes. It appears that the initial product of the reaction, toluene, is more reactive in the FriedelCrafts reaction than is benzene. Analyze the mechanism of electrophilic aromatic substitution to see why toluene is more reactive than benzene.
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