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UPSC Combined Geo-Scientist

Chemist

  • 2 objective papers
  • 120 questions each
  • 2 h per paper
  • 100 + 300 marks

Prelims Paper II covers chemistry.

UPSC Combined Geo-Scientist, Prelims · 2020 · Paper II, Chemistry · Q116 of 120

Geo-Scientist Prelims 2020 Chemistry Q116: The major product formed in the following reaction is:

QuestionOrganic / Beckmann fragmentation

The major product formed in the following reaction is:

UPSC Combined Geo-Scientist Prelims 2020 Paper II (Chemistry), Q116: figure printed with the question
UPSC Combined Geo-Scientist Prelims 2020 Paper II (Chemistry), Q116: answer options as printed
  1. (a) Ring N-hydroxyamine (alkene)
  2. (b) Trimethylcyclopentene nitrile (CN on ring)
  3. (c) Exo-methylene cyclopentyl acetonitrile
  4. (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).

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