Why is −NH2 group of aniline acetylated before carrying out nitration?
Why is −NH2 group of aniline acetylated before carrying out nitration?
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1 Answer
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This is a Short Type Questions as classified in NCERT Exemplar
Ans:
Direct nitration of aniline is not possible on account of oxidation of -NH2 group. However, nitration can be carried after protecting the -NH2 group by acetylation to give acetanilide which is then nitrated and finally hydrolysed to give o- and p-nitroanilines.
The acetyl group being electron withdrawing attracts the lone pair of electrons of the N-atom towards carbonyl group.
As a result, the activating effect -NH2 group is reduced i.e., the lone pair of electrons on nitrogen is less available for donation to benzene ring by resonance. Therefore, acti
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