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Carboxylic Acid

Organic compounds containing carboxyl groups possess sufficient acidic character and are called carboxylic acids. The carboxyl group is made up carbonyl, >C = O and hydroxyl, -OH group, hence its name is carbonyl group (carb from carbonyl and oxyl from hydroxyl). Carboxylic acids may be aliphatic (R-COOH) or aromatic (Ar-COOH) depending upon whether –COOH group is attached to aliphatic chain or aryl groups respectively.

Aliphatic monocarboxylic acids (containing one carboxyl group) are known as fatty acids because some of their higher members (C₁₂-C₁₈) like palmitic acid (C₁₅H₃₁COOH) and stearic acid (C₁₇H₃₅COOH) exist in natural fats as esters and are obtained by their hydrolysis.

Structure of carboxyl group

In carboxylic group, the bonds to the carboxyl carbon lie in one line in one plane and are separated by about 120˚. The carboxylic carbon is less electrophilic than carbonyl carbon because of the possible resonance structure shown below:

Nomenclature

The common or trivial names are derived from the source of individual acids. Formic acid, for example, was so named because it was first obtained by the distillation of ants (Latin: fomica meaning ants). Similarly, acetic acid has derived its name from vinegar (Latin: acetum meaning vinegar) butylic acid is present in butter fat (Latin: butyrum meaning butter). The positions of substituents present is specified by Greek letters etc. the carbon atom next to the carbonyl carbon is considered as –carbon.

In IUPAC system, the monocarboxylic acids are named as alkaonic acids. The name of the acid is derived by replacing the terminal ‘e’ of the corresponding alkane with ‘oic acid’. Carboxyl carbon is always given number one while numbering the carbon atoms of the parent chain. The position substituents are indicated by Arabic numerals.