anonymous
  • anonymous
Will award medal Predict the major product for the following reaction.
Chemistry
  • Stacey Warren - Expert brainly.com
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SOLVED
At vero eos et accusamus et iusto odio dignissimos ducimus qui blanditiis praesentium voluptatum deleniti atque corrupti quos dolores et quas molestias excepturi sint occaecati cupiditate non provident, similique sunt in culpa qui officia deserunt mollitia animi, id est laborum et dolorum fuga. Et harum quidem rerum facilis est et expedita distinctio. Nam libero tempore, cum soluta nobis est eligendi optio cumque nihil impedit quo minus id quod maxime placeat facere possimus, omnis voluptas assumenda est, omnis dolor repellendus. Itaque earum rerum hic tenetur a sapiente delectus, ut aut reiciendis voluptatibus maiores alias consequatur aut perferendis doloribus asperiores repellat.
schrodinger
  • schrodinger
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anonymous
  • anonymous
anonymous
  • anonymous
@Rushwr can you help me figure this out?
anonymous
  • anonymous
thatd be tight thanks

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anonymous
  • anonymous
@hartnn
Photon336
  • Photon336
@pmkat14
Photon336
  • Photon336
Let's take a look at this
Photon336
  • Photon336
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|
anonymous
  • anonymous
sorry i fugured it out i didnt realize that the oh was attached to a ethyl
anonymous
  • anonymous
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?
Photon336
  • Photon336
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|
anonymous
  • anonymous
Photon336
  • Photon336
what is your proposed mechanism @pmkat14 ?
anonymous
  • anonymous
hold on
anonymous
  • anonymous
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
anonymous
  • anonymous
donating the e- from the tertiary to the Cl, then the OH-ETH bonds to the tertiary, due to the greater alkyl substituents
anonymous
  • anonymous
|dw:1443895351946:dw|
Photon336
  • Photon336
@pmkat14 only concern i have is that if the alcohol adds to the side with the (cyclohexyl group) there would be more steric crowding
Photon336
  • Photon336
|dw:1443895796846:dw|
Photon336
  • Photon336
|dw:1443895913848:dw|
anonymous
  • anonymous
that orientation was explained to violate markonvicks rule
anonymous
  • anonymous
saying that the electrophile should go to the sp2 carbon with the most hydrogens
anonymous
  • anonymous
@Photon336
Photon336
  • Photon336
@woodward
Photon336
  • Photon336
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?

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