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Cyclohexene
Chemical compound From Wikipedia, the free encyclopedia
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Cyclohexene is a hydrocarbon with the formula (CH2)4C2H2. 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.[3]
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Production and uses
Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company.[4] 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.[5]
- C6H11OH → C6H10 + H2O
Reactions and uses
Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene.[6] Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.[7]
Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam.[8]
The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxidant in the presence of a tungsten catalyst.[9]
1,5-Hexadiene is produced by ethenolysis of cyclohexene. Bromination gives 1,2-dibromocyclohexane.[10]
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Structure
Cyclohexene is most stable in a half-chair conformation,[11] 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.
See also
References
External links
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