Question

Cis-3-tert-Butylcyclohexanol has the tert-butyl group in the equatorial position and the alcohol in the ________ position.

Answer 1

Answer:

Axial

Explanation:

In the most stable conformation of Cis-3-tert-Butylcyclohexanol, the tert-butyl group is at equatorial position and the alcohol group is in the axial position.

If the tert-butyl group is placed in equatorial position, repulsions are minimized. The bulkier the group, the greater the energy difference between the axial and equatorial conformers. Hence for a ring having a bulky substituent, such bulky substituent is better placed in the equatorial position.

The energy difference between the conformers of Cis-3-tert-Butylcyclohexanol is so high that the compound is almost "frozen" in a conformation  where the tert-butyl groups are equatorial and the -OH groups are axial. This conformer is more stable by 24 KJ/mol.