What is the mechanism for 4-bromo-2-chloroaniline from 4-bromo-2-chloroacetanilide?

On the attached picture.

Explanation:

Hello,

In this case, the required mechanism is shown on the attached picture in which it starts with the 4-bromo-2-chloroacetanilide protonation at the carboxyl group and the subsequent addition of a hydrogen to the nitrogen due to the dissociation of the employed hydrochloric acid. After that and equilibrium is shown but is affected by the presence of water which is consequently attached to the carboxyl group in order to break the N-C bond to form the required 4-bromo-2-chloroaniline (enclosed with a red line), acetic acid and hydrochloric acid by the effect of the free chloride ion which was passive until the protonated acetic acid gets neutral.

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2b2t

explanation:

2b2t