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14.1 : Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:

Acid halides Acid anhydrides Esters Amides
Figure1 Figure2 Figure3 Figure4

Cyclic esters and cyclic amides are referred to as lactones and lactams, respectively.

Figure5 Figure5

All carboxylic acid derivatives contain a carbonyl group. However, nitriles have a cyano group where a carbon atom is triply bonded to a nitrogen atom.

Figure7

Carboxylic acid derivatives in nature

Amongst the acid derivatives, acid halides and acid anhydrides are not commonly found in nature. Esters are more widespread and found in naturally occurring fats and oils. They are also responsible for the characteristic fragrance of fruits and flowers. Some examples of naturally occurring esters include:

Methyl butanoate Isopentyl acetate Butyl Acetate
Figure8 Figure9 Figure10

Amides linkages are most common in biomolecules. For example, proteins are composed of repeating amino acid units linked by an amide (CO–NH) bond.

Figure11

Tags
Carboxylic Acid DerivativesAcid HalidesAcid AnhydridesEstersAmidesLactonesLactamsNitrilesCarbonyl GroupNaturally Occurring EstersAmino AcidAmide BondProteins

From Chapter 14:

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14.1 : Carboxylic Acid Derivatives: Overview

Carboxylic Acid Derivatives

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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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14.9 : Nucleophilic Acyl Substitution 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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