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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鈮�CH.

When this acetylide anion is added to the carbonyl group thenC=O鈫�C鈭�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鈮�CH.

When this acetylide anion is added to the carbonyl group thenC=O鈫�C鈭�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

Which of the following bases could be used to deprotonate 1-butyne?

d)

The following cycloalkyne is too unstable to exist. Explain

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

a.CH3CH2CH2C鈮�CH

How would you carry out the following conversions? More than one

step is needed in each case.

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

(c) NaHCO3(pkaof H2CO36.4)

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