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Cyclohexene
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==Reactions and uses== Benzene is converted to [[cyclohexylbenzene]] by acid-catalyzed alkylation with cyclohexene.<ref>{{cite journal |doi=10.15227/orgsyn.019.0036|title=Cyclohexylbenzene|journal=Organic Syntheses|year=1939|volume=19|page=36|author=B. B. Corson, V. N. Ipatieff}}</ref> Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.<ref name="acs phenol">{{cite web |url=https://www.acs.org/content/acs/en/pressroom/cutting-edge-chemistry/what-s-new-in-phenol-production-.html |title=What's New in Phenol Production? |last=Plotkin |first=Jeffrey S. |publisher=American Chemical Society |date=2016-03-21 |access-date=2018-01-02 |archive-url=https://web.archive.org/web/20191027122212/https://www.acs.org/content/acs/en/pressroom/cutting-edge-chemistry/what-s-new-in-phenol-production-.html |archive-date=2019-10-27 |url-status=dead }}</ref> Hydration of cyclohexene gives [[cyclohexanol]], which can be [[dehydrogenation|dehydrogenated]] to give [[cyclohexanone]], a precursor to [[caprolactam]].<ref name=Ullmann>{{Ullmann|first1=Michael T.|last1= Musser|title=Cyclohexanol and Cyclohexanone|year=2005|doi=10.1002/14356007.a08_217}}</ref> The [[oxidative cleavage]] of cyclohexene gives [[adipic acid]]. [[Hydrogen peroxide]] is used as the oxidant in the presence of a tungsten catalyst.<ref>{{cite journal |title= Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid |first1= Scott M. |last1= Reed |first2= James E. |last2= Hutchison |journal= J. Chem. Educ. |year= 2000 |volume= 77 |issue= 12 |pages= 1627β1629 |doi= 10.1021/ed077p1627|bibcode= 2000JChEd..77.1627R }}</ref> [[1,5-Hexadiene]] is produced by [[ethenolysis]] of cyclohexene. Bromination gives 1,2-dibromocyclohexane.<ref>{{cite journal |doi=10.15227/orgsyn.012.0026|title=1,2-Dibromocyclohexane|journal=Organic Syntheses|year=1932|volume=12|page=26|author=H. R. Snyder, L. A. Brooks}}</ref>
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