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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4242

The compound shown and its epimer at the carbon bearing chlorine are each treated with sodium ethoxide in ethanol (E2). Select all correct statements.

  1. AThe compound shown reacts faster than its epimer.
  2. BThe epimer gives almost exclusively the less substituted alkene.
  3. CThe compound shown gives mainly the more substituted alkene.
  4. DIn the epimer chlorine is axial in the more stable chair.

Answer: A, B, C

The compound is neomenthyl chloride, with chlorine axial in the stable chair, so it has anti-periplanar hydrogens on both C-2 and C-6, reacts quickly and gives mainly the Saytzeff alkene 3-menthene. Its epimer, menthyl chloride, has chlorine equatorial; it reacts slowly through the all-axial chair and forms only 2-menthene. The last statement is therefore false.
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