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Question

Why does acetylation of NH2 group of aniline reduce its activating effect?


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Solution

Acetylation of NH2 group of aniline reduces its activating effect because the lone pair on the nitrogen atom is in conjugation with the carbonyl group in acetylated aniline. As a result, the activating effect of NH2 group is reduced i.e., the lone pair of electrons on nitrogen is less available for donation to benzene ring by resonance.




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