Which one of the following is least basic in aqueous solution

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Which one of the following is least basic in aqueous solution

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Aniline

Acetanilide

Benzamide

Both Acetanilide and Benzamide are equally basic

answer is B.

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Detailed Solution

Acetanilide is least basic because the lone pair is not only delocalized on benzene ring but also on adjacent $- CO -$ group.

In aniline lp is delocalized only on benzene ring.

In benzamide lp is delocalized only on $- CO -$ group.

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