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Question

Give reasons of the following:
Acetylation of aniline reduces its activation effect.

Solution
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Acetylation of aniline gives acetanilide, which undergoes nitration at low temperature, yielding the para-nitro product in high yield. The modifying acetyl group can then be removed by acid-catalyzed hydrolysis, to yield para-nitroaniline.

Although the activating influence of the amino group has been reduced by this procedure, the acetyl derivative remains an ortho/para-directing and activating substituent.

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