MolSynapsequestion bank
MolSynapse / Question bank / Amines and Aromatic Nitrogen Compounds / Hofmann bromamide and Gabriel synthesis on drawn substrates
JEE Advanced levelSingle correct optionDifficulty 3 of 3nc238

The optically active amide shown is treated with /aqueous . Which structure is the major product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: A

The amide shown is (S)-2-methylbutanamide. In the Hofmann rearrangement the migrating carbon moves with retention of configuration, so the amine has the same spatial arrangement. The substituent priorities stay N (replacing C=O) > ethyl > methyl > H, so the product is (S)-butan-2-amine, not the inverted or racemic form.
Practice Amines and Aromatic Nitrogen Compounds More on Hofmann bromamide and Gabriel synthesis on drawn substrates

More questions on Hofmann bromamide and Gabriel synthesis on drawn substrates