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Question 63 of 69

Q.When aniline reacts with acetic anhydride, the product formed is :

(a) p-aminoacetophenone
(b) o-aminoacetophenone
(c) acetanilide
(d) m-aminoacetophenone
Puducherry TnboardTamil Nadu HSC (DGE) Board 2024MCQ· 1mImportance★★★★★
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Aniline undergoes N-acylation with acetic anhydride: the amine nitrogen's lone pair attacks the anhydride's carbonyl carbon, displacing acetate, to give the amide acetanilide.

Aniline, C6H5NH2C_6H_5NH_2, has a nucleophilic nitrogen lone pair that attacks the electrophilic carbonyl carbon of acetic anhydride, (CH3CO)2O(CH_3CO)_2O, in a nucleophilic acyl substitution reaction. One acetyl group is transferred to nitrogen (displacing acetate/acetic acid as the leaving group), converting the -NH2_2 into an amide -NHCOCH3_3 group: C6H5NH2+(CH3CO)2O→C6H5NHCOCH3 (acetanilide)+CH3COOHC_6H_5NH_2 + (CH_3CO)_2O \rightarrow C_6H_5NHCOCH_3\ (\text{acetanilide}) + CH_3COOH The product, N-phenylacetamide, is commonly called acetanilide, and this specific N-acetylation reaction is also used industrially/in the lab to protect (and mildly deactivate) the -NH2_2 group before performing further electrophilic aromatic sub …

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