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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc183

For the Hofmann bromamide degradation, using the balanced equation , which statements are correct?

  1. AN-Methylacetamide, , gives dimethylamine under the same conditions.
  2. BAn isocyanate is an intermediate.
  3. CFour moles of are consumed per mole of amide.
  4. DThe amine contains one carbon atom less than the amide.

Answer: B, C, D

The N-bromoamide rearranges to the isocyanate, which is hydrolysed to the amine with loss of the carbonyl carbon as carbonate; the given equation uses 4 mol NaOH. The reaction needs an unsubstituted primary amide (-CONH2), so N-methylacetamide does not give dimethylamine.
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