19. Reactions of Aromatics: EAS and Beyond

Provide the major product and the correct mechanism for the following reaction.

Provide the major product and the correct mechanism for the following reaction.

To synthesize m-ethylbenzenesulfonic acid, a student attempted the Friedel–Crafts alkylation of benzenesulfonic acid with bromoethane. Do you predict that this reaction was successful? If not, propose an alternative synthesis.

In Section 23.7.4, we learned that Friedel–Crafts alkylation suffers from overalkylation.

(a) Draw the product of a Friedel–Crafts reaction that resulted in three methyl groups adding to the ring.

(b) Why is hard to stop at the addition of one alkyl group?