Ketone

Ketones are a group of organic compounds characterized by the presence of a carbonyl group in which the carbon atom is covalently bonded to an oxygen atom. The remaining two bonds are to other carbon atoms or hydrocarbon radicals (R).

Structure and properties

Ketones feature a carbonyl group (C=O) bonded to two other carbon atoms. The simplest ketone is acetone (R = R' = methyl), with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses) and the industrial solvent acetone.

Nomenclature

In the IUPAC system, ketones are named by changing the suffix -ane of the parent alkane to -anone. The position of the carbonyl group is usually denoted by a number. For the most important ketones, however, traditional nonsystematic names are still generally used, 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−CO−CH3) instead of "acetone".

Production

Ketones are produced on massive scales in industry. They are also the simplest representative of the carbonyl group of organic compounds. They are produced industrially by the oxidation of secondary alcohols.

Biological significance

Ketones are also important in biology. The most significant ketone is acetoacetate, which is generated from acetyl-CoA and can be converted into beta-hydroxybutyrate or acetone. Ketones are elevated in blood after fasting including a night of sleep, and in both blood and urine in starvation, a low carbohydrate diet, prolonged intense exercise, alcoholism, and in untreated (or inadequately treated) type 1 diabetes mellitus.

See also

• Aldehyde
• Ketosis
• Ketoacidosis

References

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Ketone

• 
  Variety of Ketones
• 
  Keto-enol tautomerism
• 
  Oxidation of a Ketone