Carboxylic acid
A carboxylic acid /ˌkɑːrbɒkˈsɪlɪk/ is an organic compound that contains a carboxyl group (C(O)OH). The general formula of a carboxylic acid is R−C(O)OH, with R referring to the rest of the (possibly quite large) molecule. Carboxylic acids occur widely and include the amino acids (which make up proteins) and acetic acid (which is part of vinegar and occurs in metabolism).
Salts and esters of carboxylic acids are called carboxylates. When a carboxyl group is deprotonated, its conjugate base forms a carboxylate anion. Carboxylate ions are resonance-stabilized, and this increased stability makes carboxylic acids more acidic than alcohols. Carboxylic acids can be seen as reduced or alkylated forms of the Lewis acid carbon dioxide; under some circumstances they can be decarboxylated to yield carbon dioxide.
Example carboxylic acids and nomenclature
Carboxylic acids are commonly named as indicated in the table below. Although rarely used, IUPAC-recommended names also exist. For example, butyric acid (C3H7CO2H) is, according to IUPAC guidelines, also known as butanoic acid.
Oxalic acid
Oxalic acid is an organic compound with the formula H2C2O4. It is a colorless crystalline solid that forms a colorless solution in water. Its condensed formula is HOOCCOOH, reflecting its classification as the simplest dicarboxylic acid. Its acid strength is much greater than that of acetic acid. Oxalic acid is a reducing agent and its conjugate base, known as oxalate (C2O42−), is a chelating agent for metal cations. Typically, oxalic acid occurs as the dihydrate with the formula H2C2O4·2H2O. Excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.
History
The preparation of salts of oxalic acid from plants had been known, at the latest, since 1745, when the Dutch botanist and physician Herman Boerhaave isolated a salt from sorrel. By 1773, François Pierre Savary of Fribourg, Switzerland had isolated oxalic acid from its salt in sorrel.
In 1776, Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman produced oxalic acid by reacting sugar with concentrated nitric acid; Scheele called the acid that resulted socker-syra or såcker-syra (sugar acid). By 1784, Scheele had shown that "sugar acid" and oxalic acid from natural sources were identical.
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