Ketone Structure Carbonyl Group Nomenclature IUPAC

A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a compound that contains this functional group. A ketone can be generally represented by the formula:

A carbonyl carbon bonded to two carbon atoms distinguishes ketones from carboxylic acids, aldehydes, esters, amides, and other oxygen-containing compounds. The double bond of the carbonyl group distinguishes ketones from alcohols and ethers.

1 Structure

1.1 Carbonyl group

A carbon atom adjacent to a carbonyl group is called an α carbon. Hydrogens attached to this carbon are called α hydrogens.

2 Nomenclature

2.1 IUPAC

Ketones are named using IUPAC nomenclatureIUPAC nomenclature is a systematic way of naming organic chemical compounds. Ideally, every organic compound should have a name from which an unambiguous structural formula can be drawn. In IUPAC nomenclature, a number of prefixes, suffixes and infixes ar by changing the suffix -e of the parent alkaneAn alkane in organic chemistry is a type of hydrocarbon in which the molecule has the maximum possible number of hydrogen atoms and so has no double bonds (they are saturated). The generic formula for acyclic alkanes, also known as aliphatic hydrocarbons to -one.

3 Physical properties

3.1 Spectroscopic properties

4 Reactions

4.1 Synthesis

Ketones can be created by oxidation of secondary alcohols. The process requires a strong oxidising agent such as potassium dichromate or other reagent containing Cr(VI). The alcohol is oxidised by heating under reflux in acidified solution. For example 2-propanol is oxidised to propanone (acetone):

Two atoms of hydrogen are removed, leaving a single oxygen atom double bonded to a carbon atom.

4.2 Reactions

4.2.1 Nucleophilic addition

4.2.2 Electrophilic addition

ketone + electrophile → resonance stabilized cation

4.2.3 Wittig reaction

- ketone + phosphonium ylide → oxphosphetane
  - oxphosphetane → phosphine oxide + alkene

4.2.4 Other

ketone + water ↔ geminal diol
ketone + thiol + acid catalyst ↔ thioacetal + water
ketone + hydrazine or derivative of hydrazine → hydrazone
ketone + metal hydride → metal alkoxide salt
- metal alkoxide salt + water → alcohol

4.3 Keto-enol tautomerism

ketone + acid catalyst ↔ enol
- enol + halogen → α- haloketone

4.4 Reactions at an α-carbon

ketone + aqueous deuterium + D⁺ or OD^- catalyst → ketone-d + HOD

5 Ketones in medicine

Acetone, acetoacetate and beta-hydroxybutyrate are ketones (or ketone bodies) generated from fatty acids in humans and most vertebrates. Ketones are elevated in blood and urine in starvation, hypoglycemia due to causes other than hyperinsulinism, various inborn errors of metabolism and some acute cases of diabetes mellitus. Although ketoacidosis is characteristic of decompensated or untreated type 1 diabetes, ketosis or even ketoacidosis can occur in type 2 diabetes in some circumstances as well. Acetoacetate and beta-hydroxybutyrate are an important fuel for many tissues, especially during fasting and starvation. The brain, in particular, relies heavily on ketone bodies during times of reduced food intake.

6 Ketones in perfume

Ketones are often used in perfumes and paints to stabilize the other ingredients so that they don't degrade over time as quickly.

7 Examples

8 See also

Functional groups Ketones

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