Formula C6H10 Density 811 kg/m³ | Molar mass 82.143 g/mol | |
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Cyclohexene chair
Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid 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.
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Production and uses
Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company. It is converted to cyclohexanol, which is dehydrogenated to give cyclohexanone, a precursor to caprolactam. Cyclohexene is also a precursor to adipic acid, maleic acid, dicyclohexyladipate, and cyclohexene oxide. Furthermore, it is used as a solvent.
Synthesis
A common experiment for beginning organic chemistry students is the acid-catalyzed dehydration of cyclohexanol with distillative removal of the resulting cyclohexene from the reaction mixture:
Oxidative cleavage
A green chemistry experiment is the oxidative cleavage of cyclohexene to form adipic acid. Hydrogen peroxide is used as the oxidant, in the presence of a tungsten catalyst.
Structure
Cyclohexene is most stable in a half-chair conformation, unlike the preference for a chair for 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.
