Question

Draw the structures of all possible products formed in the following reaction involving an acid anhydride dissolved in alcohol.

Answer 1

General guidance

Concepts and reason

Acid anhydride undergoes a reaction with alcohol to form ester and carboxylic acid. The acid anhydride undergoes three steps to form ester.

The steps include nucleophilic attack of alcohol, cleavage of leaving group, and protonation.

Fundamentals

Nucleophilic attack of alcohol:

Cleavage of leaving group:

Protonation:

Step-by-step

Step 1 of 2

Explanation | Common mistakes | Hint for next step

The lone pair electron of oxygen in ethanol undergoes the nucleophilic attack on carbonyl carbon of acid anhydride, which creates a negative charge on carbonyl oxygen. The double bond of carbon \u2013 oxygen bond is reformed by the cleavage of leaving group. The leaving group undergoes protonation and stabilizes the positive charge of oxygen, and gives ester, carboxylic acid as product.

Step 2 of 2

The lone pair electron of oxygen in ethanol undergoes the nucleophilic attack on another carbonyl carbon of acid anhydride and creates a negative charge on carbonyl oxygen. The carbon \u2013 oxygen double bond is reformed again by the cleavage of leaving group. The leaving group undergoes protonation and stabilizes the positive charge of oxygen, and gives ester, carboxylic acid as product.

Answer

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