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13.1: IUPAC Nomenclature of Carboxylic Acids

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Organic Chemistry

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IUPAC Nomenclature of Carboxylic Acids
 
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13.1: IUPAC Nomenclature of Carboxylic Acids

IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.

For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.

Figure1

Numbering the parent carbon chain is performed starting from the –COOH carbon. The names and positions of the substituent are then listed alphabetically as a prefix to the parent name. Some examples are given below:

Figure2

It is to be noted that all other functional groups like -CHO, -CO-, -OH, -OR, -NH2, and halogens are given less priority over the –COOH group, and thus they are treated as substituents in the presence of –COOH groups.

Unsaturated carboxylic acids are named after the parent alkene or alkyne. The position of multiple bonds is indicated by a locant prefixed to the parent alkene or alkyne. The cis/trans or E/Z notations are prefixed to the parent alkene to indicate the stereochemistry around the double bond.

Figure3

Acyclic dicarboxylic acids have similar nomenclature rules, except that the terminal -e of the parent hydrocarbon is retained, and a suffix -dioic acid is added.

Figure4

Compounds containing more than two –COOH groups are sometimes named by treating one of them as a substituent. For example, the carboxylic acid shown below treats the –CH2COOH group as a substituent and uses the prefix carboxymethyl- to the parent name.

Figure5

In the case of cyclic carboxylic acids having –COOH groups directly attached to a cycloalkane ring or an aromatic ring, a suffix -carboxylic acid is added to the parent ring name. However, unlike acyclic carboxylic acids, the ring carbon attached to the –COOH group is numbered as carbon-1.

Figure6

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Keywords: IUPAC Nomenclature Carboxylic Acids Acyclic Saturated Monocarboxylic Acids Parent Chain Substituents Unsaturated Carboxylic Acids Acyclic Dicarboxylic Acids Cyclic Carboxylic Acids

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