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Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H.  Carboxylic acids are Bronsted/Lowry acids — they are proton donors. Salts and anions of carboxylic acids are called carboxylates.
Carboxylic acids are polar, and form hydrogen bonds with each other. At high temperatures, in vapor phase, carboxylic acids usually exist as dimeric pairs. Lower carboxylic acids (1 to 4 carbons) are miscible with water, whereas higher carboxylic acids are very much less-soluble due to the increasing hydrophobic nature of the alkyl chain. They tend to be rather soluble in less-polar solvents such as ethers and alcohols.
Carboxylic acids are widespread in nature and are typically weak acids, meaning that they only partially dissociate into H+ cations and RCOO− anions in aqueous solution. For example, at room temperature, only 0.02 % of all acetic acid molecules are dissociated in water.
Since the carboxylic acids are weak acids, in water, both forms exist in an equilibrium:
Stability of the acid
Using inductive effects, the acidity of carboxylic acids can be rationalized by the two electronegative oxygen atoms distorting the electron clouds surrounding the O-H bond, weakening it. The weak O-H bond causes the acid molecule to be less stable, and causing the hydrogen atom to be labile, thus it dissociates easily to give the H+ ion. Since the acid is unstable, the equilibrium will lie on the right.
Additional electronegative atoms or groups, such as chlorine or hydroxyl, substituted on the R-group have a similar, though lesser effect. The presence of these groups increases the acidity through inductive effects. For example, trichloroacetic acid (three -Cl groups) is a stronger acid than lactic acid (one -OH group), which in turn is stronger than acetic acid (no electronegative constituent).
Stability of the conjugate base
The acidity of a carboxylic acid can also be explained by resonance effects. The result of the dissociation of a carboxylic acid is a resonance stabilized product in which the negative charge is shared (delocalized) between the two oxygen atoms. Each of the carbon-oxygen bonds has what is called a partial double-bond characteristic. Since the conjugate base is stabilized, the above equilibrium lies on the right.
Carboxylic acids are most readily identified as such by infrared spectrometry. They exhibit a sharp C=O stretch between 1680 and 1725 cm−1, and the characteristic O-H stretch of the carboxyl group appears as a broad peak in the 2500 to 3000 cm−1 region.
In 1H NMR spectrometry, the hydroxyl hydrogen appears in the 10-13 ppm region, though it is often either broadened or not observed due to exchange with any traces of water.
Lower straight-chain aliphatic carboxylic acids, as well as those of even carbon number up to C18, are commercially available. For example, acetic acid is produced by methanol carbonylation with carbon monoxide, whereas long chain carboxylic acids are obtained by the hydrolysis of triglycerides obtained from plant or animal oils.
Vinegar, a dilute solution of acetic acid, is biologically produced from the fermentation of ethanol. It is used in food and beverages, but is not used in industry.
Carboxylic acids may also form from the following reactions:
Nomenclature and examples
The carboxylate anion R-COO– is usually named with the suffix -ate, so acetic acid, for example, becomes acetate ion. In IUPAC nomenclature, carboxylic acids have an -oic acid suffix (e.g., octadecanoic acid). In common nomenclature, the suffix is usually -ic acid (e.g., stearic acid).
Other carboxylic acids include:
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Carboxylic_acid". A list of authors is available in Wikipedia.|