Question

Describe the changes in hydrocarbon structure and functional groups that are needed to make cortisone from cholesterol (see Fig. 7.39).

Short answer

The below-mentioned changes in hydrocarbon structure and functional groups are needed to make cortisone from cholesterol.

Step-by-step solution

The following changes are needed to make cortisone from cholesterol.

The carbon-hydroxyl C–OH group bond on ring one (1) should be replaced with a carbon-oxygen C=O double bond.

The carbon-carbon (C-C) sigma bond on ring two (2) should be moved to ring one (1).

A carbon-oxygen C=O double bond should be introduced in ring three (3).

The hydrocarbon side chain on ring four (4), together with a hydrogen (H) atom, should be replaced with a hydroxyl (-OH) ion and a ${\text{- COCH}}_{\text{2}}\text{OH}$group.

The structure of the cholesterol and cortisone are shown below.