Answered: The reaction of an ester with an amine…

The reaction of an ester with an amine is not as slow as the reaction of an ester with water or an alcohol. Explain with reason.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 30VC

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

The reaction of an ester with an amine is not as slow as the reaction of an ester with water or an alcohol. Explain with reason.
Explain why the rate of aminolysis of an ester cannot be increased by H+, OH- or OR-.
How can you activate the carboxylic acid?
Is acid catalyzed hydrolysis of acetamide a reversible or an irreversible reaction. Explain.

Definition Definition Organic compounds with a nitrogen atom having a lone pair of electrons on it. Amines are derived from ammonia (NH 3 ), wherein hydrogen atoms are substituted by an aryl or alkyl group.

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