MolSynapsequestion bank
MolSynapse / Question bank / Stereoisomerism / Conformational analysis of ethane, butane and cyclohexane
JEE Advanced levelSingle correct optionDifficulty 3 of 3st215

Menthol is (1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol (OH on C1, isopropyl on C2, CH on C5). Which of the following stereoisomers can adopt a chair in which all three substituents are equatorial?

  1. A(1S,2S,5R)
  2. B(1R,2S,5R)
  3. C(1R,2S,5S)
  4. D(1R,2R,5R)

Answer: B

All-equatorial requires OH/iPr trans (1,2), OH/CH cis (1,3-relationship via C1 and C5) and iPr/CH trans (1,4-relationship). Translating the descriptors into up/down relationships (from CIP assignments): (1R,2S,5R) satisfies all three; (1S,2S,5R) has OH cis to iPr; (1R,2S,5S) has OH trans to CH; (1R,2R,5R) has all three cis. So only (1R,2S,5R), natural menthol, is all-equatorial.
Practice Stereoisomerism More on Conformational analysis of ethane, butane and cyclohexane

More questions on Conformational analysis of ethane, butane and cyclohexane