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Ketones are produced when the body burns fat for energy or fuel. They are
also produced when you lose weight or if there is not enough insulin to help your
body use sugar for energy. Without enough insulin, glucose builds up in the blood.
Since the body is unable to use glucose for energy, it breaks down fat instead. Any
of a class of organic compounds characterized by the presence of a carbonyl
group in which the carbonatom is covalently bonded to an oxygen atom. The
remaining two bonds are to other carbon atoms or hydrocarbon radicals. Ketone
compounds have important physiological properties. They are found in
severalsugars and in compounds for medicinal use, including natural and
synthetic steroid
hormones.
Molecules
of
the
anti-inflammatory
agent cortisone contain three ketone groups.
Only a small number of ketones are manufactured on a large scale in
industry. They can be synthesized by a wide variety of methods, and because of
their ease of preparation, relative stability, and high reactivity, they are nearly ideal
chemical intermediates. Many complex organic compounds are synthesized using
ketones as building blocks. They are most widely used as solvents, especially in
industries manufacturing explosives, lacquers, paints, andtextiles. Ketones are also
used in tanning, as preservatives, and in hydraulic fluids.
The most important ketone is acetone (CH3COCH3), a liquid with a sweetish
odour. Acetone is one of the few organic compounds that is infinitely soluble
in water (i.e., soluble in all proportions); it also dissolves many organic compounds.
For this reasonand because of its low boiling point (56 C [132.8 F]), which makes
it easy to remove by evaporation when no longer wantedit is one of the most
important
industrial
solvents,
being
used
in
such
products
as
paints, varnishes, resins, coatings, and nail-polish removers.
Nomenclature of ketones
The International Union of Pure and Applied Chemistry (IUPAC) name of a
ketone is derived by selecting as the parent the longest chain of carbon atoms that
contains the carbonyl group. The parent chain is numbered from the end that gives
the carbonyl carbon the smaller number. The suffix -e of the parent alkane is
changed to -one to show that the compound is a ketone. For example,
Reactions of ketones
Ketones are highly reactive, although less so than aldehydes, to which they
are closely related. Much of their chemical activity results from the nature of
the carbonyl group. Ketones readily undergo a wide variety of chemical reactions. A
major reason is that the carbonyl group is highly polar; i.e., it has an uneven
distribution of electrons. This gives the carbon atom a partial positive charge,
making it susceptible to attack by nucleophiles, which are species attracted to
positively charged centres. Typical reactions includeoxidation-reduction and
nucleophilic addition. The polarity of the carbonyl group affects the physical
properties of ketones as well.
Secondary alcohols are easily oxidized to ketones (R2CHOH R2CO). The
reaction can be halted at the ketone stage because ketones are generally resistant
to further oxidation.
Oxidation of a secondary alcohol to a ketone can be accomplished by many
oxidizing agents, most often chromic acid (H 2CrO4), pyridinium chlorochromate
(PCC), potassium permanganate (KMnO 4), or manganese dioxide (MnO 2). With a few
exceptions (such as oxidative cleavage of cyclohexanone, C 6H10O, to adipic acid,
HO2C[CH2]4CO2H, a compound used to make nylon-6,6), the oxidation of ketones is
not synthetically useful.
The treatment of an aromatic hydrocarbon with an acyl halide or anhydride in
the presence of a catalyst composed of a Lewis acid (i.e., a compound capable of
accepting an electron pair), most often aluminum chloride (AlCl 3), gives an aryl alkyl
or diaryl ketone (ArH ArCOR or ArCOAr), where Ar represents an aromatic ring.
This reaction is known as Friedel-Crafts acylation.
Ketones possessing -hydrogens can often be made to undergo aldol reactions (also
calledaldol condensation) by the use of certain techniques. The reaction is often
used to close rings, in which case one carbon provides the carbonyl group and
another provides the carbon with an -hydrogen. An example is the synthesis of 2cyclohexenone. In this example, the aldol productundergoes loss of H 2O to give an
,
-unsaturated
ketone.