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JEE Main levelSingle correct optionDifficulty 2 of 3o4237

The compound shown is treated with a strong base. Compared with its diastereomer, its E2 elimination is

  1. Athe same, because the tert-butyl group is too far from chlorine to matter
  2. Bslower, because both groups must be axial to react
  3. Cfaster, because the chair with the tert-butyl group equatorial places chlorine axial
  4. Dslower, because chlorine is equatorial in the chair with the tert-butyl group equatorial

Answer: C

The compound is trans-1-tert-butyl-3-chlorocyclohexane. A 1,3-trans relationship means one group axial and one equatorial, so with the large tert-butyl group equatorial the chlorine is axial and can be anti-periplanar to axial beta-hydrogens. The cis isomer would have chlorine equatorial and react far more slowly.
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