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Cyclohexene is a
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
with the formula C6H10. This cycloalkene is a colorless
liquid A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, an ...
with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms
peroxides In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable. The most common peroxide is hydrogen ...
.


Production and uses

Cyclohexene is produced by the partial
hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate org ...
of
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen ato ...
, a process developed by the Asahi Chemical company. In the laboratory, it can be prepared by dehydration of cyclohexanol. : :


Reactions and uses

Benzene is converted to
cyclohexylbenzene Cyclohexylbenzene is the organic compound with the structural formula C6H5-C6H11. It is a derivative of benzene with a cyclohexyl substituent (C6H11). It is a colorless liquid. Formation Cyclohexylbenzene is produced by the acid-catalyzed alky ...
by acid-catalyzed alkylation with cyclohexene. Cyclohexylbenzene is a precursor to both phenol and cyclohexanone. Hydration of cyclohexene gives cyclohexanol, which can be
dehydrogenated In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...
to give cyclohexanone, a precursor to caprolactam. The oxidative cleavage of cyclohexene gives adipic acid.
Hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3% ...
is used as the oxidant in the presence of a tungsten catalyst. Bromination gives 1,2-dibromocyclohexane.


Structure

Cyclohexene is most stable in a half-chair conformation, unlike the preference for a chair form of
cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohex ...
. One basis for the cyclohexane conformational preference for a chair is that it allows each bond of the ring to adopt a staggered conformation. For cyclohexene, however, the alkene is planar, equivalent to an eclipsed conformation at that bond.


See also

* Diels-Alder reaction * Cyclohexa-1,3-diene * Cyclohexa-1,4-diene


External links

* *
Material Safety Data Sheet for cyclohexene




* ttp://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0183 Cyclohexene synthesis
Data sheet at inchem.org


References

{{cycloalkenes Cycloalkenes Hydrocarbon solvents Foul-smelling chemicals