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Diketone
 
 
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A diketone is a molecule containing two ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 groups. The simpliest diketone is diacetyl
Diacetyl

Diacetyl is a natural byproduct of fermentation . It is a Vicinal diketone with the chemical formula C4H6O2....
, also known as 2,3-butanedione. Diacetyl, acetylacetone
Acetylacetone

Acetylacetone is an organic compound with molecular formula C5H8O2. This diketone is formally named 2,4-pentanedione....
, and hexane-2,5-dione
Hexane-2,5-dione

Hexane-2,5-dione, carbonhydrogenoxygen, is a diketone and a toxic metabolite of hexane....
 are examples of 1,2-, 1,3-, and 1,4-diketones, respectively. Dimedone
Dimedone

Dimedone is a cyclic diketone used in organic chemistry to determine whether a compound contains an aldehyde group. Cyclohexanediones in general can be used as catalysts in the formation of transition-metal complexes....
 is an example of a cyclic diketone.

Diketones, such as acetylacetone, are particularly prone to form stable enols or enolates because of conjugation
Conjugated system

A conjugated system occurs in an organic compound where atoms covalently Chemical bond with alternating single and multiple bonds and influence each other to produce a region called electron delocalization....
 of the enol or enolate with the other carbonyl group, and the stability gained in forming a six-membered ring, (hydrogen bonded in the case of the enol or containing the counter ion in the case of the enolate).

The conjugate base derived from 1,3-ketones form complexes with metal ions.

Diketones with one or two methylene groups separating the carbonyl groups typically coexist with their enol tautomer
Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. Commonly this reaction results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond....
s.






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Diacetyl Structure
A diketone is a molecule containing two ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 groups. The simpliest diketone is diacetyl
Diacetyl

Diacetyl is a natural byproduct of fermentation . It is a Vicinal diketone with the chemical formula C4H6O2....
, also known as 2,3-butanedione. Diacetyl, acetylacetone
Acetylacetone

Acetylacetone is an organic compound with molecular formula C5H8O2. This diketone is formally named 2,4-pentanedione....
, and hexane-2,5-dione
Hexane-2,5-dione

Hexane-2,5-dione, carbonhydrogenoxygen, is a diketone and a toxic metabolite of hexane....
 are examples of 1,2-, 1,3-, and 1,4-diketones, respectively. Dimedone
Dimedone

Dimedone is a cyclic diketone used in organic chemistry to determine whether a compound contains an aldehyde group. Cyclohexanediones in general can be used as catalysts in the formation of transition-metal complexes....
 is an example of a cyclic diketone.

Reactions

1,3-Diketones, such as acetylacetone, are particularly prone to form stable enols or enolates because of conjugation
Conjugated system

A conjugated system occurs in an organic compound where atoms covalently Chemical bond with alternating single and multiple bonds and influence each other to produce a region called electron delocalization....
 of the enol or enolate with the other carbonyl group, and the stability gained in forming a six-membered ring, (hydrogen bonded in the case of the enol or containing the counter ion in the case of the enolate).

The conjugate base derived from 1,3-ketones form complexes with metal ions.

Diketones with one or two methylene groups separating the carbonyl groups typically coexist with their enol tautomer
Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. Commonly this reaction results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond....
s. The reactions of such dicarbonyls are very similar to those of simple ketones.

EU Regulation

In 2004, the EU conducted an examination of certain flavoring additives grouped together as "Flavouring Group Evaluation FGE.11". This group included diketones. As part of that study, the EU found that acetylacetone (pentane-2,4-dione) (FL 07.191) was genotoxic
Genotoxic

Genotoxicity describes a deleterious action on a cell genetic material affecting its integrity. Genotoxic substances are known to be potentially mutagenic or carcinogen, specifically those capable of causing genetic mutation and of contributing to the development of tumors....
 in vivo and in vitro, and deleted it from the register of permitted flavoring substances. The register of permitted flavoring substances was adopted in 1999.