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 ex ...

with the formula C₆H₁₀. This

cycloalkene A cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms and either one or more double bonds, but has no aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene, can be used as m ...

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, a ...

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 p ...

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 Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or S ...

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 atoms, ...

, a process developed by the Asahi Chemical company. In the laboratory, it can be prepared by dehydration of

cyclohexanol Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, w ...

. :

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 alkyla ...

by acid-catalyzed alkylation with cyclohexene. Cyclohexylbenzene is a precursor to both phenol and cyclohexanone. Hydration of cyclohexene gives

, 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 Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohexan ...

, a precursor to

caprolactam Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately five million tons per year, and the vast majority is used ...

. The

oxidative cleavage Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions, because many reactions carr ...

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). Cyclohexan ...

. One basis for the

cyclohexane conformation In organic chemistry, cyclohexane conformations are any of several three-dimensional shapes adopted by molecules of cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane are ...

al preference for a chair is that it allows each bond of the ring to adopt a

staggered conformation In organic chemistry, a staggered conformation is a chemical conformation of an ethane-like Moiety (chemistry), moiety abcX–Ydef in which the substituents a, b, and c are at the maximum distance from d, e, and f; this requires the torsion ang ...

. For cyclohexene, however, the alkene is planar, equivalent to an eclipsed conformation at that bond.

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

Production and uses

Reactions and uses

Structure

See also

External links

References