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Chapter 9: Q51E (page 286)

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

Expert verified

The structure of acetylide anion is -C≡CH.

When this acetylide anion is added to the carbonyl group thenC=O→C−OH . The Carbonyl group gives a nucleophilic addition reaction. The acetylide anion adds to the carbonyl group.

Step by step solution

01

Addition of acetylide anion

The structure of acetylide anion is -C≡CH.

When this acetylide anion is added to the carbonyl group thenC=O→C−OH . The Carbonyl group gives a nucleophilic addition reaction. The acetylide anion adds to the carbonyl group.

02

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

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Most popular questions from this chapter

Using any alkyne needed, how would you prepare the following alkenes?

(c) 3-Methyl-1-pentene

Question: How would you carry out the following reactions?

The pkaof acetone, CH3COCH3, is 19.3. Which of the following bases is strong enough to deprotonate acetone?

(c) NaHCO3(pkaof H2CO36.4)

Using any alkyne needed, how would you prepare the following alkenes?

(a) trans-2-Octene

What products would you expect from the following reactions?

b.
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