In
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, ...
a hydroxy ketone (often referred to simply as a ketol) is a
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ...
consisting of a
ketone flanked by a
hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydro ...
group. In the two main classes, the hydroxyl group can be placed in the
alpha position (an alpha-hydroxy ketone RCR′(OH)(CO)R) or in the beta position (a beta-hydroxy ketone, RCR′(OH)CR
2(CO)R).
* An α-hydroxy ketone can consist of either a
primary alcohol
A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group.
In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary a ...
(e.g.
hydroxyacetone
Hydroxyacetone, also known as acetol, is the organic chemical with the formula CH3C(O)CH2OH. It consists of a primary alcohol substituent on acetone. It is an α-hydroxyketone, also called a ketol, and is the simplest hydroxy ketone structure. ...
) or a secondary alcohol; the latter are often broadly referred to as
acyloin
Acyloins or α-hydroxy ketones are a class of organic compounds which all possess a hydroxy group adjacent to a ketone group. The name acyloin is derived from the fact that they are formally derived from reductive coupling of carboxylic acyl grou ...
s
* Prominent β-hydroxy ketones are
aldol adduct
The aldol reaction is a means of forming carbon–carbon bonds in organic chemistry.
Discovered independently by the Russian chemist Alexander Borodin in 1869 and by the French chemist Charles-Adolphe Wurtz in 1872, the reaction combines two c ...
s.
* Only terminal α-hydroxy ketones can give positive
Fehling's test
In organic chemistry, Fehling's solution is a chemical reagent used to differentiate between water-soluble carbohydrate and ketone () functional groups, and as a test for reducing sugars and non-reducing sugars, supplementary to the Tollens' r ...
.
References
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