Chapter 5, Problem 24P

Interpretation Introduction

Interpretation:

The most stable configuration of $\text{2-isopropyl-5-methylcyclohexanol}$ is to be drawn, the configuration of the hydroxyl group to the isopropyl group and to the methyl group is to be identified. The most stable structure of neo-menthol is to be written.

Concept introduction:

Cyclohexane is present in chair form as it is a non-planar ring.

The chair form of cyclohexane has axial and equatorial bonds.

When a cyclohexane bears two or more substituents on different carbons, then the conformation that has the larger substituent in an equatorial position is most stable.