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In Hoffmann reaction,Why N-substituted amides not undergo this rearrangement?

In Hoffmann reaction,Why N-substituted amides not undergo this rearrangement?

Grade:12th pass

1 Answers

Souvik Mukherjee
50 Points
6 years ago
In Hoffmann reaction, the reaction initiates with the abstraction of a proton (H+) from the amide -NH2 group by the base OH- in the very first step. But N-substituted amides lack this H to be abstracted as proton (H+) by base OH-. Thus they are reluctant to undergo the rearrangement.

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