Question

In the reduction of 4-tert-butylcyclohexanone with sodium borohydride, the major product has the tert-butyl group in the equatorial position and the alcohol in the ________ position.

Answer 1

Answer:

Axial position

Explanation:

In the reduction of 4-tert-butylcyclohexanone with sodium borohydride, the major product has the tert-butyl group in the equatorial position and the alcohol in the axial position.

The reason for this is that, axial bonds are parallel to each other. If  substituents are larger than hydrogen, they experience a greater steric crowding in axial compared to the equatorial position. Therefore, many substituted cyclohexane compounds prefer a conformation in which the larger substituents are in equatorial position.