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14.9 : Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.

  1. Addition: Nucleophilic attack at the carbonyl carbon, forming a tetrahedral intermediate.
  2. Elimination: Departure of the leaving group.

The net outcome of the addition–elimination reaction is the conversion of one acyl derivative into another. The reaction can be carried out in the presence of an acid or a base catalyst depending on the reactivity of the acyl derivative.

Figure1

Tags
Nucleophilic Acyl SubstitutionCarboxylic Acid DerivativesSubstitution ReactionsNucleophileAcyl CompoundLeaving GroupAddition elimination MechanismTetrahedral IntermediateAcid CatalystBase Catalyst

From Chapter 14:

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14.9 : Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

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14.1 : Carboxylic Acid Derivatives: Overview

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14.2 : Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

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14.3 : Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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14.4 : Structures of Carboxylic Acid Derivatives

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14.5 : Physical Properties of Carboxylic Acid Derivatives

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14.6 : Acidity and Basicity of Carboxylic Acid Derivatives

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14.7 : Spectroscopy of Carboxylic Acid Derivatives

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14.8 : Relative Reactivity of Carboxylic Acid Derivatives

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14.10 : Acid Halides to Carboxylic Acids: Hydrolysis

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14.11 : Acid Halides to Esters: Alcoholysis

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14.12 : Acid Halides to Amides: Aminolysis

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14.13 : Acid Halides to Alcohols: LiAlH<sub>4</sub> Reduction

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14.14 : Acid Halides to Alcohols: Grignard Reaction

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14.15 : Acid Halides to Ketones: Gilman Reagent

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