Chapter 6.5, Problem 6.33P

Interpretation Introduction

Interpretation:

Chair flip has to be done for the given conformation and other chair conformation has to be drawn.

Concept Introduction:

When a compound contains a cyclohexane ring in it, then there are three possibilities of conformations.  They are chair, boat and twist-boat.  Among these three conformations of cyclohexane ring, the most stable one is the chair conformation.

In the above structure, there are twelve substituents that can be placed.  Among the twelve, six are axial substituents and six are equatorial substituents.  The axial substituents can be represented as shown below,

The equatorial substituents can be represented as,

To draw a group in a correct configuration, we have to understand what is coming towards us and what is going away from us (wedge and dash bonds).

For drawing the other chair conformation, a ring flip has to be done.  Ring flipping makes the skeleton as shown below,

During this ring flip (chair flip) from one chair conformation to another, all the substituents present in axial position goes to equatorial position and vice-versa.