Chapter 4, Problem 4.13P

Interpretation Introduction

Interpretation:

The most stable conformation of the molecule shown is to be drawn.

Concept introduction:

When the bulkier substituent attached to a cyclohexane ring is in the equatorial position, the chair conformation is more favored. In the disubstituted cyclohexane, the substituents that are on the opposite side of the ring are trans to each other. If there are more than one substituent attached, then the conformation in which maximum substituents are in the equatorial position is favored and is more stable. Substituents that are trans to each other in one chair conformation remain trans after the chair flip.