Which of the following will not give the Hoff | vedclass

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(C) The Hoffmann bromamide degradation reaction is specific to primary amides $(R-CONH_2)$. In this reaction,a primary amide reacts with bromine in th

Vedclass · Accepted Answer

$CH_3CONHCH_3$

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(C) The Hoffmann bromamide degradation reaction is specific to primary amides $(R-CONH_2)$. In this reaction,a primary amide reacts with bromine in the presence of an aqueous or ethanolic solution of sodium hydroxide to form a primary amine with one carbon atom less than the original amide. Compounds $CH_3CONH_2$,$C_6H_5CONH_2$,and $CH_3CH_2CONH_2$ are all primary amides and will undergo this reaction. However,$CH_3CONHCH_3$ is an $N$-substituted amide (a secondary amide). Since it does not have two hydrogen atoms on the nitrogen atom,it cannot form the necessary $N$-bromamide intermediate required for the rearrangement step of the Hoffmann bromamide degradation. Therefore,$CH_3CONHCH_3$ will not give this reaction.

Which of the following will not give the Hoffmann bromamide degradation reaction?

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