Question

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

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

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.

Explanation

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

First Step

Stepwise Mechanism