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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4220

2,2-Dimethylcyclohexanol is heated with conc. . The major alkene is:

  1. A3,3-dimethylcyclohexene
  2. B1,6-dimethylcyclohexene
  3. C1,2-dimethylcyclohexene
  4. D1-isopropylcyclopentene

Answer: C

The secondary cation at C1 has a quaternary neighbour (C2), so a 1,2-methyl shift gives the tertiary cation at C2 (C1 now carries H and ). Loss of the C1 proton gives the tetrasubstituted alkene 1,2-dimethylcyclohexene, the most stable, as the major product. Loss from C3 would give the less substituted 1,6-dimethylcyclohexene.
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