Cyclohexene is a hydrocarbon with the formula Template:Chem2. It is a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. Among its uses, it is an intermediate in the commercial synthesis of nylon.<ref>Template:Cite journal</ref>
Production and usesEdit
Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company.<ref>Template:Cite patent</ref> The main product of the process is cyclohexane because cyclohexene is more easily hydrogenated than benzene.
In the laboratory, it can be prepared by dehydration of cyclohexanol.<ref>Template:Cite journal</ref>
Reactions and usesEdit
Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene.<ref>Template:Cite journal</ref> Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.<ref name="acs phenol">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam.<ref name=Ullmann>Template:Ullmann</ref>
The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxidant in the presence of a tungsten catalyst.<ref>Template:Cite journal</ref>
1,5-Hexadiene is produced by ethenolysis of cyclohexene. Bromination gives 1,2-dibromocyclohexane.<ref>Template:Cite journal</ref>
StructureEdit
Cyclohexene is most stable in a half-chair conformation,<ref>Template:Cite journal</ref> unlike the preference for a chair form of cyclohexane. 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.