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14.1: Carboxylic Acid Derivatives: Overview

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JoVE Core
Organic Chemistry

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Carboxylic Acid Derivatives: Overview
 
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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   

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Keywords: Carboxylic Acid Derivatives Acid Halides Acid Anhydrides Esters Amides Lactones Lactams Nitriles Carbonyl Group Naturally Occurring Esters Amino Acid Amide Bond Proteins

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