Question

Which has a higher percentage of the diequatorial-substituted conformer compared with the diaxialsubstituted conformer: trans-1,4-dimethylcyclohexane or cis-1-tert-butyl-3-methylcyclohexane?

Answer 1

Answer:

cis-1-tert-butyl-3-methylcyclohexane will have a higher percentage of the diequatorial-substituted conformer when compared with the diaxialsubstituted conformer.

Explanation:

The two compound contain or have high stability with the substituent group is at equatorial position but the tert-betyl group in cis-1-tert-butyl-3-methylcyclohexane is larger than the methyl group in trans-1,4-dimethylcyclohexane.

Thus, the equatorial position will be more favorable for the substituent group in the cis-1-tert-butyl-3-methylcyclohexane, therefore having higher percentage of the diequatorial substituted conformer compared with that of diaxial-substituted conformer.