19. Reactions of Aromatics: EAS and Beyond

Propose a mechanism for each of the following reactions:

b.

Benzene undergoes electrophilic aromatic substitution reactions with aziridines in the presence of a Lewis acid such as AlCl₃.

a. What are the major and minor products of the following reaction?

b. Would you expect epoxides to undergo similar reactions?

Propose a mechanism for each of the following reactions:

a.

Phenolphthalein, a common nonprescription laxative, is also an acid–base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

a. Propose a mechanism for the synthesis of phenolphthalein.