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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4012

2,2-Dimethylcyclohexanol is heated with concentrated . The major alkene and the key step leading to it are

  1. A1,2-dimethylcyclohexene, formed by direct loss of H from C-2
  2. B1,2-dimethylcyclohexene, formed after a 1,2-methyl shift
  3. C1,6-dimethylcyclohexene, formed after a 1,2-methyl shift
  4. D3,3-dimethylcyclohexene, formed directly without a shift

Answer: B

Ionisation gives the secondary cation at C-1, next to the quaternary C-2, which has no hydrogen. A 1,2-methyl shift from C-2 to C-1 produces the tertiary cation at C-2 (bearing a methyl group). Loss of the tertiary H on C-1 gives the tetrasubstituted 1,2-dimethylcyclohexene, the Saytzeff product.
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