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Why is NHX2 group of aniline acetylated before carrying out nitration? - Chemistry

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प्रश्न

Why is \[\ce{NH2}\] group of aniline acetylated before carrying out nitration?

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उत्तर

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, activating effect of –NHCOCH3 group is less than that of the –NH2 group.

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पाठ 13: Amines - Multiple Choice Questions (Type - I) [पृष्ठ १८८]

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एनसीईआरटी एक्झांप्लर Chemistry [English] Class 12
पाठ 13 Amines
Multiple Choice Questions (Type - I) | Q 39 | पृष्ठ १८८

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