orgo 8r

[pistolpete007]

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on the solution of 85...it starts with cyclohexane---Br2/hv--> bromocylohexane---------C3H5O-Na in EtOH------>cyclohexene ALTHOUGH i do AGREE with this rxn....it said the last part was E2 Rxn can someone tell me why...EtOH is a protic solvent so wouldnt that make it E1 cuz i thought E2 cant have protic solvents only aprotic?

 

[happyasaclam88]

E2 can be a competing reaction under pretty much any circumstances ... although polar aprotic solvents generally increase the rate of sn2/e2 reactions, they can still take place under protic situations. even if this wasn't the case, a bulky nucleophile like ethoxide really doesn't have a good place to attack the hexane, so it makes sense to that elimination would happen.