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JEE Main levelSingle correct optionDifficulty 2 of 3o4240

The compound shown (a menthane skeleton) is heated with sodium ethoxide in ethanol. Which structure is the major alkene?

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

Answer: A

The compound is neomenthyl chloride, in which chlorine is axial (cis to the isopropyl group) in the stable chair with the other two groups equatorial. The C-2 hydrogen, which carries the isopropyl group, is axial and anti to chlorine, as is the C-6 hydrogen. The Saytzeff product, the trisubstituted 3-menthene, therefore forms as the major alkene.
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