why the acetylation requires one mole of acetic anhydride per mole of aniline, though acetic anhydride contains two acetyl groups. How is the by-product containing the second acetyl group removed from acetanilide?

why the acetylation requires one mole of acetic anhydride per mole of aniline, though acetic anhydride contains two acetyl groups. How is the by-product containing the second acetyl group removed from acetanilide?

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 70AP

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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.

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Explain why the acetylation requires one mole of acetic anhydride per mole of aniline, though acetic anhydride contains two acetyl groups. How is the by-product containing the second acetyl group removed from acetanilide?

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