Cis-1,3-Dimethylcyclohexane Contains Considerably Smaller Percentage of Diaxial Conformation Than Trans-1,2-Dimethylcyclohexane

Essay

Cis-1,3-dimethylcyclohexane contains considerably smaller percentage of diaxial conformation than trans-1,2-dimethylcyclohexane. However, cis-cyclohexane-1,3-diol has a higher percentage diaxial conformation than trans-cyclohexane-1,2-diol. (For purposes of this problem, you can assume that an -OH group and a -CH₃ group have about the same size.) Explain this difference. A drawing of the diaxial chair conformation of cis-cyclohexane-1,3-diol must be part of your answer.