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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 halidesAcid anhydridesEstersAmides
Figure1Figure2Figure3Figure4

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 butanoateIsopentyl acetateButyl Acetate
Figure8Figure9Figure10

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

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