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Write the Chemical Equations Involved in the Following Reactions:(I) Hoffmann-bromamide Degradation Reaction - Chemistry

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Answer in Brief

Write the chemical equations involved in the following reactions:(i) Hoffmann-bromamide degradation reaction

Illustrate the following reaction giving suitable example in each case:

Hoffmann bromamide degradation reaction

Write the reactions involved in Hofmann bromamide degradation reaction

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Solution 1

a. Primary amine can be prepared by reaction of the amide with bromine and aqueous or alcoholic
sodium hydroxide. This reaction is known as Hoffmann bromamide degradation

b. It involves molecular rearrangement.

c. An alkyl or aryl group migrates from the carbonyl carbon to the adjacent nitrogen atom.

d. This reaction is useful for decreasing the length of carbon chain by one carbon atom.

\[\ce{CH3 - CO - NH2 + 4NaOH + Br2 ->CH3  - NH2 + Na2CO3 + 2NaBr + 2H2O}\]

Solution 2

\[\ce{R - CH2 - CO - NH2 + 4NaOH + Br2 ->R - CH2 - NH2 + Na2CO3 + 2NaBr + 2H2O}\]

\[\ce{CH3 - CH2 - CO - NH2 + 4NaOH + 2NaBr + 2H2O->CH3 - CH2 - NH2 + Na2CO3 + 2NaBr + 2H2O}\]

Concept: Amines - Preparation of Amines
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