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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

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14.1 : Carboxylic Acid Derivatives: Overview

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14.2 : Nomenclatura de los derivados del ácido carboxílico: halogenuros ácidos, ésteres y anhídridos ácidos

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14.3 : Nomenclatura de los derivados del ácido carboxílico: amidas y nitrilos

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14.4 : Estructuras de los derivados del ácido carboxílico

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14.5 : Propiedades físicas de los derivados del ácido carboxílico

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14.6 : Acidez y basicidad de los derivados del ácido carboxílico

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14.7 : Espectroscopía de derivados del ácido carboxílico

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14.8 : Reactividad relativa de los derivados del ácido carboxílico

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14.9 : Sustitución nucleofílica de acilo de derivados del ácido carboxílico

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14.10 : Halogenuros ácidos a ácidos carboxílicos: hidrólisis

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14.11 : Halogenuros ácidos a ésteres: alcoholisis

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14.12 : Halogenuros ácidos a amidas: aminolis

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14.13 : Halogenuros ácidos a alcoholes: reducción de LiAlH4

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14.14 : Halogenuros ácidos a alcoholes: reacción de Grignard

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14.15 : Halogenuros ácidos a cetonas: reactivo de Gilman

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