After completing this section, you should be able to
- list a number of naturally occurring carboxylic acids.
- state one of the industrial uses of acetic acid.
The global demand for acetic acid is about 6.5 million tonnes per year. A common industrial preparation of acetic acid is the catalytic oxidation of methanol with carbon monoxide. Much of the acetic acid produced is converted to vinyl acetate polymer and used in adhesives and paints.
Not only are carboxylic acids valuable, but they and their derivatives are useful starting materials for many synthetic products. Finally, carboxylic acids and their derivatives are also found in a variety of natural systems and important biological pathways.
Serving wine usually involves a rather elaborate ceremony in which the host tastes the wine before pouring it for the guests. One reason for this is the possibility that the wine may have been spoiled by exposure to air.
Certain bacterial enzymes are capable of converting ethanol to ethanoic acid (acetic acid) when oxygen is present:
The same reaction occurs when cider changes into vinegar, which contains 4 to 5 percent acetic acid. Acetic acid gives vinegar its sour taste and pungent odor and can do the same thing to wine.
Acetic acid, CH3COOH, is an example of the class of compounds called carboxylic acids, each of which contains one or more carboxyl groups, COOH. The general formula of a carboxylic acid is RCOOH. Some other examples are
Formic acid (the name comes from Latin word formica meaning “ant“) is present in ants and bees and is responsible for the burning pain of their bites and stings. Butyric acid, a component of rancid butter and Limburger cheese, has a vile odor. Adipic acid is an example of a dicarboxylic acid—it has two functional groups—and is used to make nylon.
Carboxylic Acid Derivatives
Other functional group combinations with the carbonyl group can be prepared from carboxylic acids, and are usually treated as related derivatives. Five common classes of these carboxylic acid derivatives are listed in the following table. Although nitriles do not have a carbonyl group, they are included here because the functional carbon atoms all have the same oxidation state. The top row (yellow shaded) shows the general formula for each class, and the bottom row (light blue) gives a specific example of each. As in the case of amines, amides are classified as 1º, 2º or 3º, depending on the number of alkyl groups bonded to the nitrogen.
Functional groups of this kind are found in many kinds of natural products. Some examples are shown below with the functional group colored red. Most of the functions are amides or esters, cantharidin being a rare example of a natural anhydride. Cyclic esters are called lactones, and cyclic amides are referred to as lactams. Penicillin G has two amide functions, one of which is a β-lactam. The Greek letter locates the nitrogen relative to the carbonyl group of the amide.
- William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry