Question

Explain why we did not synthesize acetanilide by refluxing a mixture of aniline and

Answer 1

Answer:-

If we directly refluxed the mixture of aniline and acetic anhydride, the acetylation could occur multiple times, resulting in a multi acetylated compound .

In order to prevent this problem, the aniline is first converted to a soluble salt. Now it can then be acetylated at manageable slow rates.

Answer 2

The aniline is not refluxed with the acetic anhydride in order to prevent the acetylation reaction taking place multiple times.

Synthesis of acetanilide  from aniline

The synthesis of acetanilide  from aniline occurs when the aniline is converted to salt and refluxed with acetic anhydride in the presence of glacial acetic acid. The anine group is the nucleophile while the carbonyl group is the electrophile.

The aniline is not refluxed with the acetic anhydride in order to prevent the acetylation reaction taking place multiple times.

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