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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4073

trans-(2-Methylcyclohexyl)trimethylammonium hydroxide ( on C-1, methyl on C-2, trans) is heated. The major alkene is

  1. A3-methylcyclohexene
  2. B2-methylcyclohexanol
  3. Cmethylenecyclohexane
  4. D1-methylcyclohexene

Answer: A

Hofmann elimination is an anti E2, so the trimethylammonium group and the beta hydrogen must be trans-diaxial. In the reactive trans-diaxial chair, the methyl on C-2 is axial and C-2 has no axial hydrogen, so only the axial hydrogen on C-6 is anti. Removal of it gives the C-1=C-6 alkene, 3-methylcyclohexene, which is also the Hofmann-type product.
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