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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 dei derivati dell'acido carbossilico: alogenuri acidi, esteri e anidridi acide

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14.3 : Nomenclatura dei derivati dell'acido carbossilico: ammidi e nitrili

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14.4 : Strutture dei derivati dell'acido carbossilico

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14.5 : Proprietà fisiche dei derivati dell'acido carbossilico

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14.6 : Acidità e basicità dei derivati dell'acido carbossilico

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14.7 : Spettroscopia di derivati dell'acido carbossilico

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14.8 : Reattività relativa dei derivati dell'acido carbossilico

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14.9 : Sostituzione nucleofila acilica di derivati dell'acido carbossilico

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14.10 : Alogenuri acidi in acidi carbossilici: idrolisi

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14.11 : Alogenuri acidi a esteri: Alcolysis

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14.12 : Alogenuri acidi ad ammidi: amminolisi

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14.13 : Alogenuri acidi in alcoli: Riduzione LiAlH4

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14.14 : Alogenuri acidi in alcoli: reazione di Grignard

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14.15 : Alogenuri acidi in chetoni: reagente Gilman

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