19. Reactions of Aromatics: EAS and Beyond
Electrophilic Aromatic Substitution
5PRACTICE PROBLEM
The electrophilic aromatic substitution reaction rate for indole is 1013 times greater than that of benzene. It often reacts under mild reaction conditions. Substitution in indole occurs preferably at position 3.
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Propose a mechanism for the bromination of indole. You do not have to show steps for generating the Br+ ion. You may begin with indole and Br+ ion. Draw resonance forms for each sigma complex.
The electrophilic aromatic substitution reaction rate for indole is 1013 times greater than that of benzene. It often reacts under mild reaction conditions. Substitution in indole occurs preferably at position 3.
Propose a mechanism for the bromination of indole. You do not have to show steps for generating the Br+ ion. You may begin with indole and Br+ ion. Draw resonance forms for each sigma complex.