cyclohexene

Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company.{{cite patent|title=Cyclohexanol, method for producing cyclohexanol, and method for producing adipic acid|pubdate=26 Sep 2017|inventor-last=Narisawa|inventor2-last=Tanaka|inventor-first=Naoki|inventor2-first=Katsutoshi|country=US|number=9771313}} 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.{{cite journal |doi=10.15227/orgsyn.005.0033|title=Cyclohexene|journal=Organic Syntheses|year=1925|volume=5|page=33|author=G. H. Coleman, H. F. Johnstone}}

:{{chem2|C6H11OH -> C6H10 + H2O}}

Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene.{{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}} Cyclohexylbenzene is a precursor to both phenol and cyclohexanone.{{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 }}

Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam.{{Ullmann|first1=Michael T.|last1= Musser|title=Cyclohexanol and Cyclohexanone|year=2005|doi=10.1002/14356007.a08_217}}

The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxidant in the presence of a tungsten catalyst.{{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= 1627–1629 |doi= 10.1021/ed077p1627|bibcode= 2000JChEd..77.1627R }}

1,5-Hexadiene is produced by ethenolysis of cyclohexene. Bromination gives 1,2-dibromocyclohexane.{{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}}

Cyclohexene is most stable in a half-chair conformation,{{cite journal |title= Conformational preferences and interconversion barriers in cyclohexene and derivatives |first1= Frederick R. |last1= Jensen |first2= C. Hackett |last2= Bushweller |journal= J. Am. Chem. Soc. |year= 1969 |volume= 91 |issue= 21 |pages= 5774–5782 |doi= 10.1021/ja01049a013}} 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

{{Reflist}}

• {{ICSC|1054|10}}
• {{PGCH|0167}}
• [https://web.archive.org/web/20120328181429/http://hazard.com/msds/mf/baker/baker/files/c7073.htm Material Safety Data Sheet for cyclohexene]
• [https://web.archive.org/web/20071022034608/http://physchem.ox.ac.uk/MSDS/CY/cyclohexene.html Safety MSDS data]
• [https://web.archive.org/web/20070503012733/http://www.uni-regensburg.de/Fakultaeten/nat_Fak_IV/Organische_Chemie/Didaktik/Keusch/D-Addit_ar-e.htm Reaction of Cyclohexene with Bromine and Potassium Permanganate]
• [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0183 Cyclohexene synthesis]
• [http://www.inchem.org/documents/sids/sids/110838.pdf Data sheet at inchem.org]

{{cycloalkenes}}

Category:Cycloalkenes

Category:Hydrocarbon solvents