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Write the chemical equation involved in the following reaction: Hoffmann-bromamide degradation reaction - Chemistry

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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.

Chemical Equations/Structures
Very Long Answer
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Solution 1

  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.
  2. It involves molecular rearrangement.
  3. An alkyl or aryl group migrates from the carbonyl carbon to the adjacent nitrogen atom.
  4. This reaction is useful for decreasing the length of carbon chain by one carbon atom.
    \[\ce{CH3 - CO - NH2 + 4NaOH + Br2 ->CH3  - NH2 + Na2CO3 + 2NaBr + 2H2O}\]
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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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2014-2015 (March) Panchkula Set 1

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\[\begin{array}{cc}
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||\phantom{.......................}\\
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\end{array}\]


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