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Grade 12th passOrganic Chemistry

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

Profile image of THAKOR JUNED
8 Years agoGrade 12th pass
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1 Answer

Profile image of Souvik Mukherjee
8 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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