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In: Chemistry

Draw the organic products formed in the following reaction.

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Expert Solution

Concepts and reason

Amide hydrolysis is a process where an amide is hydrolyzed and forms a carboxylate ion in the presence of a base. In the presence of an acid, amide hydrolysis ends up with carboxylic acid and an ammonia derivative. Amide hydrolysis follows the mechanism of ester hydrolysis under basic conditions.

Fundamentals

- Amide hydrolysis under basic media produces the carboxylate ion and ammonia derivative. First, the base attacks the positively charged carbon atom in the carbonyl group of amide and forms oxy anion. Then, the oxy anion stabilizes to form carboxylic acid by giving the amine derivative. Under basic conditions, the carboxylic acid formed loses the proton to form a carboxylate ion.

- General amide hydrolysis under basic conditions

Given amide is shown below.

Base attack on the carbonyl group of the amide

Oxy anion is formed during the attack of the base on a carbonyl group of amide. The base attacks the partially positive carbon atom of the carbonyl group and produces the oxyanion, where the negative charge lies on the more electronegative oxygen atom.

Oxyanion

Stabilization of oxyanion

Stabilization of oxyanion to carboxylic acid is a slow step process, whereas carboxylic acid to carboxylate conversion in the presence of a base is very rapid.

The complete reaction

Stabilization of oxyanion to carboxylic acid is a slow step process while carboxylic acid to carboxylate conversion in the presence of a base is very rapid. An amide ion abstracts the acidic proton from the carboxylic acid very rapidly and forms a carboxylate ion. The carboxylate ion is highly stabilized through resonance.

The complete reaction

Dr. OWL answered 3 years ago

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Question

Draw the organic products formed in the following reaction.

Solutions

Expert Solution

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