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UPSC Combined Geo-Scientist

Chemist

  • 3 descriptive papers
  • 200 marks each
  • 3 h per paper

Mains Paper III covers analytical and organic chemistry.

UPSC Combined Geo-Scientist, Mains · 2022 · Mains Paper III

Q6(d). HCl with 1-methyl-1-vinylcyclobutane: ring expansion

Question

Write the mechanism for the following conversion. [1-methyl-1-vinylcyclobutane treated with HCl; scheme given in the paper]

Answer in brief

Protonation gives a secondary carbocation; a ring C–C bond shifts (ring expansion) to give a tertiary cyclopentyl cation, which takes up Cl⁻.

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Coversring expansioncarbocation rearrangement1,2-alkyl shiftHCl additionMarkovnikov