Ketone

In organic chemistry, a ketone /ˈkiːtoʊn/ is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)− (a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' are methyl), with the formula (CH₃)₂CO. Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, e.g., testosterone, and the solvent acetone.

The word ketone is derived from Aketon, an old German word for acetone.

According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix -ane of the parent alkane to -anone. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names, although some introductory chemistry textbooks use systematic names such as "2-propanone" or "propan-2-one" for the simplest ketone (CH₃−C(=O)−CH₃) instead of "acetone".

The derived names of ketones are obtained by writing separately the names of the two alkyl groups attached to the carbonyl group, followed by "ketone" as a separate word. Traditionally the names of the alkyl groups were written in order of increasing complexity, for example methyl ethyl ketone. However, according to the rules of IUPAC nomenclature, the alkyl groups are written alphabetically, for example ethyl methyl ketone. When the two alkyl groups are the same, the prefix "di-" is added before the name of alkyl group. The positions of other groups are indicated by Greek letters, the α-carbon being the atom adjacent to carbonyl group.

Although used infrequently, oxo is the IUPAC nomenclature for the oxo group (=O) and used as prefix when the ketone does not have the highest priority. Other prefixes, however, are also used. For some common chemicals (mainly in biochemistry), keto refer to the ketone functional group.

The ketone carbon is often described as sp² hybridized, a description that includes both their electronic and molecular structure. Ketones are trigonal planar around the ketonic carbon, with C–C–O and C–C–C bond angles of approximately 120°. Ketones differ from aldehydes in that the carbonyl group (C=O) is bonded to two carbons within a carbon skeleton. In aldehydes, the carbonyl is bonded to one carbon and one hydrogen and are located at the ends of carbon chains. Ketones are also distinct from other carbonyl-containing functional groups, such as carboxylic acids, esters and amides.

The carbonyl group is polar because the electronegativity of the oxygen is greater than that for carbon. Thus, ketones are nucleophilic at oxygen and electrophilic at carbon. Because the carbonyl group interacts with water by hydrogen bonding, ketones are typically more soluble in water than the related methylene compounds. Ketones are hydrogen-bond acceptors. Ketones are not usually hydrogen-bond donors and cannot hydrogen-bond to themselves. Because of their inability to serve both as hydrogen-bond donors and acceptors, ketones tend not to "self-associate" and are more volatile than alcohols and carboxylic acids of comparable molecular weights. These factors relate to the pervasiveness of ketones in perfumery and as solvents.

Ketones are classified on the basis of their substituents. One broad classification subdivides ketones into symmetrical and unsymmetrical derivatives, depending on the equivalency of the two organic substituents attached to the carbonyl center. Acetone and benzophenone ((C₆H₅)₂CO) are symmetrical ketones. Acetophenone (C₆H₅C(O)CH₃) is an unsymmetrical ketone.