MolSynapsequestion bank
MolSynapse / Question bank / Amines and Aromatic Nitrogen Compounds / Preparation of amines: Gabriel, Hofmann bromamide, reduction routes
JEE Advanced levelSingle correct optionDifficulty 3 of 3nc180

Assertion: Hofmann bromamide degradation of an optically active amide in which R is chiral at the carbon attached to C=O gives an amine of retained configuration. Reason: The R group migrates from carbon to nitrogen with inversion of configuration while forming the isocyanate.

  1. ABoth Assertion and Reason are true and the Reason is the correct explanation of the Assertion
  2. BAssertion is true but Reason is false
  3. CAssertion is false but Reason is true
  4. DBoth Assertion and Reason are true but the Reason is not the correct explanation of the Assertion

Answer: B

The migrating group moves with its bonding electrons to the electron-deficient nitrogen in a concerted step and keeps its configuration (retention). The Assertion is therefore true and the Reason, which claims inversion, is false.
Practice Amines and Aromatic Nitrogen Compounds More on Preparation of amines: Gabriel, Hofmann bromamide, reduction routes

More questions on Preparation of amines: Gabriel, Hofmann bromamide, reduction routes