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JEE Main levelSingle correct optionDifficulty 2 of 3o4179

cis- and trans-1-tert-butyl-4-chlorocyclohexane are each treated with in ethanol. The tert-butyl group is so large that it stays equatorial in both. Which statement is correct?

  1. AThe trans isomer reacts faster because its equatorial chlorine is less hindered
  2. BThe cis isomer reacts much faster because its chlorine is axial and has anti-periplanar axial beta-hydrogens
  3. CBoth isomers react at the same rate because both have the same leaving group
  4. DThe trans isomer reacts faster because it can ring flip freely to put chlorine axial

Answer: B

With tert-butyl equatorial, the cis isomer (1,4-cis) has chlorine axial and two axial beta-hydrogens anti to it, so E2 is easy. In the trans isomer chlorine is equatorial and no beta C-H bond is anti-periplanar to it; a ring flip would force the tert-butyl group axial, which is very unfavourable.
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