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JEE Main levelSingle correct optionDifficulty 2 of 3st206

Consider cis-1-tert-butyl-4-methylcyclohexane. Take the A-value of CH as and that of tert-butyl as much larger. Which statement is correct?

  1. AIn the preferred chair both groups are equatorial; the cis isomer is more stable than the trans isomer
  2. BIn the preferred chair the tert-butyl group is axial and the methyl is equatorial
  3. CIn the preferred chair the tert-butyl group is equatorial and the methyl is axial; the cis isomer is about 7 kJ/mol less stable than the trans isomer
  4. DIn the preferred chair both groups are axial; the cis isomer is more stable than the trans isomer

Answer: C

In a 1,4-relationship cis means (a,e) or (e,a). The tert-butyl group is locked equatorial, so the methyl must be axial in the cis isomer, costing about 7.3 kJ/mol. In the trans isomer both groups are equatorial (e,e) with no such penalty, so the trans isomer is more stable by roughly 7 kJ/mol.
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