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Chemistry LibreTexts

Hofmann rearrangement

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Hofmann rearrangement, also known as Hofmann degradation and not to be confused with Hofmann elimination, is the reaction of a primary amide with a halogen (chlorine or bromine) in strongly basic (sodium or potassium hydroxide) aqueous medium, which converts the amide to a primary amine. For example:

hofmannrearrangement1.png

Mechanism:

hofmannrearrangement2.png


Hofmann rearrangement is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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