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JEE Main levelSingle correct optionDifficulty 2 of 3o2240

The alkene shown reacts with . Which structure is the major product?

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

Answer: D

The alkene is methylenecyclobutane. Protonation of the exocyclic gives the tertiary 1-methylcyclobutyl cation, which is already the stable site, so there is no ring expansion. Bromide capture gives 1-bromo-1-methylcyclobutane.
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