QuestionOrganic / Beckmann fragmentation
The major product formed in the following reaction is:


- (a) Ring N-hydroxyamine (alkene)
- (b) Trimethylcyclopentene nitrile (CN on ring)
- (c) Exo-methylene cyclopentyl acetonitrile
- (d) α-Campholenonitrile
Answer: (d)
Camphor oxime + acid: the C–C bond anti to OH can break to give a stable tertiary cation instead of normal Beckmann migration → fragmentation to a nitrile; loss of H⁺ gives the alkene: α-campholenonitrile → (d).