Cyclohexene

Cyclohexene is produced by the partial hydrogenationofbenzene, a process developed by the Asahi Chemical company.^[3] The main product of the process is cyclohexane because cyclohexene is more easily hydrogenated than benzene.

In the laboratory, it can be prepared by dehydrationofcyclohexanol.^[4]

C₆H₁₁OH → C₆H₁₀ + H₂O

Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene.^[5] Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.^[6]

Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam.^[7]

The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxidant in the presence of a tungsten catalyst.^[8]

Bromination gives 1,2-dibromocyclohexane.^[9]

Cyclohexene is most stable in a half-chair conformation,^[10] 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.

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

• International Chemical Safety Card 1054
• NIOSH Pocket Guide to Chemical Hazards. "#0167". National Institute for Occupational Safety and Health (NIOSH).
• Material Safety Data Sheet for cyclohexene
• Safety MSDS data
• Reaction of Cyclohexene with Bromine and Potassium Permanganate
• Cyclohexene synthesis
• Data sheet at inchem.org