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Questions
Write the chemical equation involved in the following reaction:
Hoffmann-bromamide degradation reaction
Illustrate the following reaction giving a suitable example in the case:
Hoffmann bromamide degradation reaction
Write the reactions involved in Hofmann bromamide degradation reaction
Write the chemical equation involved in Hoffmann Bromamide degradation for acetamide.
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Solution 1
- 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.
- It involves molecular rearrangement.
- An alkyl or aryl group migrates from the carbonyl carbon to the adjacent nitrogen atom.
- 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
\[\ce{R - CO - NH2 + 4NaOH + Br2 ->R - CH2 - NH2 + Na2CO3 + 2NaBr + 2H2O}\]
\[\ce{CH3 - CH2 - CO - NH2 + 4NaOH + 2NaBr + 2H2O->CH3 - CH2 - NH2 + Na2CO3 + 2NaBr + 2H2O}\]
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\[\begin{array}{cc}
\ce{O}\phantom{.......................}\\
||\phantom{.......................}\\
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