19. Reactions of Aromatics: EAS and Beyond
Electrophilic Aromatic Substitution
2:36 minutes
Problem 17-10c
Textbook Question
Textbook QuestionIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly with bromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions, however, and the yields (mostly m-nitroaniline) are poor.
(c) Although nitration of aniline is slow and gives mostly meta substitution, nitration of acetanilide (PhNHCOCH3) goes quickly and gives mostly para substitution. Use resonance forms to explain this difference in reactivity.
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