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19.20 : Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.

Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide to a free amide. Amides are stable molecules that are less nucleophilic and basic than amines, making them useful functionalities in electrophilic aromatic substitutions. For instance, the direct bromination of aniline usually results in a tribrominated product as a result of the strongly activating amino group. However, if the amino group is first acylated and then brominated, a monobrominated product can be obtained.

Tags
AcylationAminesAmidesCarboxylic Acid DerivativesAcid ChloridesEstersAnhydridesNucleophileTetrahedral IntermediateBr nsted BaseElectrophilic Aromatic SubstitutionAnilineBromination

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19.20 : Amines to Amides: Acylation of Amines

Amines

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19.1 : Amines: Introduction

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19.2 : Nomenclature of Primary Amines

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19.3 : Nomenclature of Secondary and Tertiary Amines

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19.4 : Nomenclature of Aryl and Heterocyclic Amines

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19.5 : Structure of Amines

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19.6 : Physical Properties of Amines

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19.7 : Basicity of Aliphatic Amines

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19.8 : Basicity of Aromatic Amines

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19.9 : Basicity of Heterocyclic Aromatic Amines

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19.10 : NMR Spectroscopy Of Amines

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19.11 : Mass Spectrometry of Amines

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19.12 : Preparation of Amines: Alkylation of Ammonia and Amines

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19.13 : Preparation of 1° Amines: Azide Synthesis

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19.14 : Preparation of 1° Amines: Gabriel Synthesis

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