Chapter 27.SE, Problem 39AP

Interpretation Introduction

Interpretation:

The three-dimentional conformation of digitoxigenin is to be drawn indicating whether the two hydroxyl groups are axial or equatorial.

Concept introduction:

If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis, then a hydrogen at one ring junction is axial while that in the other junction is equatorial.

Among the disubstituted cyclohexanes, 1,2- cis, 1,3- trans and 1,4-cis substituents will have axial and equatorial arrangements. 1,2-trans, 1,3-cis and 1,4-trans substituents will have either diequatorial or diaxial arrangements.

To draw:

The three-dimentional conformation of digitoxigenin, indicating whether the two hydroxyl groups are axial or equatorial.