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Why is α-chloro-2,6-dimethylacetanilide much less basic than 2,6-dimethylaniline?

Why is α-chloro-2,6-dimethylacetanilide much less basic than 2,6-dimethylaniline?

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Answer #1

α-chloro-2,6-dimethylacetanilide is prepared the by the reaction between 2,6-dimethylaniline and α-chloroacetyl chloride.

In 2,6-dimethylaniline, lone pair of electrons is localized on the nitrogen where as in α-chloro-2,6-dimethylacetanilide lone pair is delocalized between the nitrogen and Oxygen through resonance.

Hence α-chloro-2,6-dimethylacetanilide (Presence of Amide group) is less basic than 2,6-dimethylaniline ( Presence of Amine group)

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