Question

The oral contraceptive agent Mestranol is synthesized using a carbonyl addition reaction like that shown in Problem 9-50. Draw the structure of the ketone needed.

Short answer

The structure of acetylide anion is ${}^{-}\mathbf{C}\equiv \mathbf{CH}$.

When this acetylide anion is added to the carbonyl group then$\mathrm{C}=\mathrm{O}\to \mathrm{C}-\mathrm{OH}$ . The Carbonyl group gives a nucleophilic addition reaction. The acetylide anion adds to the carbonyl group.

Step-by-step solution

Addition of acetylide anion

The structure of acetylide anion is ${}^{-}\mathbf{C}\equiv \mathbf{CH}$.

When this acetylide anion is added to the carbonyl group then$\mathrm{C}=\mathrm{O}\to \mathrm{C}-\mathrm{OH}$ . The Carbonyl group gives a nucleophilic addition reaction. The acetylide anion adds to the carbonyl group.

Mechanism of the reaction

The alkyne act as the nucleophile and attacks the carbonyl compound center and lead to the formation of chiral center.

Mechanism