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@Rushwr can you help me figure this out?
thatd be tight thanks
Let's take a look at this
When we take look at this this is our starting material, now I want us to work through this step by step. @pmkat14 this is our starting material. |dw:1443894657460:dw|
sorry i fugured it out i didnt realize that the oh was attached to a ethyl
but actually, the chlorine would bond to the secondary C due to the presence of more H? and the OH-ETH would go to the tertiary beacause there are more alkyl substituents?
our double bonds contain pi electrons that are mobile, these will act as a nucleophile. interestingly enough we see that there's a chlorine, |dw:1443894762161:dw| |dw:1443894862379:dw| i think chlorine would compete with the alcohol, you could possibly get a mixture |dw:1443895004103:dw|
what is your proposed mechanism @pmkat14 ?
dotation of the pi bond to the Cl then Cl as a eaving group, then the Cl forms a three member ring with the tertiary and secondary C
donating the e- from the tertiary to the Cl, then the OH-ETH bonds to the tertiary, due to the greater alkyl substituents
@pmkat14 only concern i have is that if the alcohol adds to the side with the (cyclohexyl group) there would be more steric crowding
that orientation was explained to violate markonvicks rule
saying that the electrophile should go to the sp2 carbon with the most hydrogens
I strongly feel that both structures are possible. @pmkat14 my argument was sterics. I guess the nucleophile would add to the more substituted side. leading to the structure you drew, but I still believe that you would get some of the other product too. @aaronq thoughts?