Question

With organolithium and organomagnesium compounds, approach to the carbonyl carbon from the less hindered direction is generally preferred. Assuming that this is the case, draw the structure of the major product formed when 4-tert-butylcyclohexanone reacts with phenylmagnesium bromide, followed by treatment with aqueous acid.

Answer 1

trans-4-tert-butyl-1-phenylcyclohexanol

Step-by-step explanation:

The bulky tert-butyl group will occupy the equatorial position in the cyclohexanone ring.

It will hinder approach of the Grignard reagent from the bottom side of the molecule.

The reagent will attack from the top, so the product alcohol will be

trans-4-tert-butyl-1-phenylcyclohexanol.