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Chapter 21: 86P (page 817)

Draw a stepwise mechanism for the following reaction, a key step in the synthesis of conivaptan (trade name Vaprisol), a drug used in the treatment of low sodium levels.

Short Answer

Expert verified

The nucleophilic attack occurs on the electrophilic position. The carbon bonded to the Cl, Br, I is more electrophilic, therefore, the nucleophile attacks on the carbon.

The carbonyl carbon also undergoes the nucleophilic attack and forms the respective product.

Step by step solution

01

Nucleophilic attack

The nucleophilic attack occurs on the electrophilic position. The carbon bonded to the Cl, Br, I is more electrophilic, therefore, the nucleophile attacks on the carbon.

The carbonyl carbon also undergoes the nucleophilic attack and forms the respective product.

02

Explanation

The step-by-step reaction mechanism is as follows:

First Step

Stepwise Mechanism

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Most popular questions from this chapter

Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomersformed in this reaction from both A and B. Explain why this process gives an opticallyinactive product mixture from A, and an optically active product mixture from B.

Give the IUPAC name for each aldehyde.

a.

b.

c

What products are formed when each acetal is hydrolyzed with aqueous acid?

a.

b.

Give the IUPAC name for each aldehyde.

a.2-isobutyl-3-isopropylhexanal

b. trans-3-methylcyclopentanecarbaldehyde

c. 1-methylcyclopropanecarbaldehyde

d. 3,6-diethylnonanal

Which carbonyl group in each pair absorbs at a higher frequency?

a.

b.
See all solutions

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