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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.

Chemical structure diagram of 3-Hydroxy-2-methylbutanoic acid, indicating molecular configuration.

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:

Chemical structure diagram of four isomeric pentanoic acids with substituents, showing molecular formulas.

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.

Chemical structure diagram of (E)-4-Hydroxy-7-oxo-5-heptenoic acid and 4-Methyl-2-pentynoic acid.

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.

2-Ethylpentanedioic acid chemical structure, molecular formula, organic chemistry diagram.

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.

Chemical structure diagram of 3-(carboxymethyl)hexanedioic acid molecule, displaying bonds and atoms.

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.

Chemical structure diagram of cycloalkane carboxylic acids with labeled substituents and rings.

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IUPAC NomenclatureCarboxylic AcidsAcyclic Saturated Monocarboxylic AcidsParent ChainSubstituentsUnsaturated Carboxylic AcidsAcyclic Dicarboxylic AcidsCyclic Carboxylic Acids

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13.1 : IUPAC Nomenclature of Carboxylic Acids

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13.2 : カルボン酸の物性

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13.3 : カルボン酸の酸性度

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13.4 : カルボン酸の酸性度に対する置換基の影響

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13.5 : カルボン酸のIRおよびUV-Vis分光法

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13.6 : NMRとカルボン酸の質量分析

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