Login processing...

Chapter 14: Carboxylic Acid Derivatives Back To Chapter

14.1: Carboxylic Acid Derivatives: Overview

TABLE OF
CONTENTS

JoVE Core
Organic Chemistry

A subscription to JoVE is required to view this content.

Education

Carboxylic Acid Derivatives: Overview

Next Video

Next Video
14.2: Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Embed Languages Add to Favorites ADD TO PLAYLIST

TRANSCRIPT

The general formula of a carboxylic acid is RCOOH. Here, an acyl group is attached to a hydroxyl group by a single bond.

Carboxylic acid derivatives are compounds where the hydroxyl group is replaced by other functional groups.

For example, replacing the hydroxyl group with a halide forms acyl halides like acetyl chloride, and substitution with an amino group gives amides such as acetamide and cyclic amides like caprolactam.

Similarly, replacing the hydroxyl group with an alkoxy group yields esters such as methyl acetate and cyclic esters like caprolactone.

Furthermore, substitution with an acyloxy group forms acid anhydrides like acetic anhydride and cyclic analogues like succinic anhydride.

Thus, each derivative contains an acyl group attached to a heteroatom.

However, nitriles are also classified as carboxylic acid derivatives, although they lack an acyl group. Instead, they contain a cyano group where a carbon atom is triply bonded to a nitrogen atom, such as acetonitrile.

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

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

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.

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

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

Tags

Carboxylic Acid Derivatives Acid Halides Acid Anhydrides Esters Amides Cyclic Esters Cyclic Amides Lactones Lactams Carbonyl Group Nitriles Cyano Group Naturally Occurring Esters Methyl Butanoate Isopentyl Acetate Butyl Acetate Biomolecules Proteins

X

Simple Hit Counter