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Define Hofmann degradation reaction

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Define Hofmann degradation reaction

Posted by Pushpraj Singh Rajput 4 years, 2 months ago

CBSE > Class 12 > Chemistry

1 answers

Gaurav Seth 4 years, 2 months ago

When amide is treated with Br2 in aqueous or ethanolic solution of NaOH, degradation of amide results in formation of primary amine.
Primary amine formed contains one carbon less than the number of carbon atoms in amide.

∣∣

R−C−NH2+Br2+4NaOH⟶R−NH2+Na2CO3+2NaBr+2H2O

Mechanism:

Base attacks amide deprotonating it and generating anion.
Anion reacts with Br2 forming bromoamide.
Deprotonation of bromoamide occurs forming bromoamide anion which undergoes rearrangement forming isocyanate.
Isocyanate forms carbamic acid by addition of H2O molecules.
Decarboxylation of carbamic acid occurs forming primary amine.

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