Q51E - Organic Chemistry (Mcmurry)

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.

Step-by-Step Solution

Answer

Step 1: 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.

Step 2: 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