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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4239

The compound shown is treated with sodium ethoxide in ethanol and reacts by E2. Which structure is the major alkene?

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

Answer: D

The compound is trans-1-bromo-2-methylcyclohexane. The diequatorial chair has no anti-periplanar hydrogen, so the ring flips to the diaxial chair, where the methyl group is axial and the C-2 hydrogen is equatorial. Only the axial hydrogen on C-6 is anti to bromine, so elimination gives the less substituted 3-methylcyclohexene instead of the Saytzeff alkene.
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