Chapter 3, Problem 64P

Interpretation Introduction

Interpretation:

Check whether the trans-1,4-dimethylcyclohexane or cis-1-tertbutyl-3-methylcyclohexane will have a higher percentage of the diequatorial-substituted conformer compared with the diaxial-substituted conformer.

Concept introduction:

The axial substituent interferes with the axial hydrogens on C3 and C5 carbons. This interference generally called as 1, 3-diaxial interaction.

Considering, $\text{1,4-disubstitutedcyclohexane}$ the same substituents on the axial or equatorial position gives the trans isomer while the same substituent on the axial and equatorial position gives the cis isomer.

Among this the equatorial isomer is more stable due to the absence of $\text{1,3-diaxial}\text{interactions}$.