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anonymous

  • one year ago

Will award medal Predict the major product for the following reaction.

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  1. anonymous
    • one year ago
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  2. anonymous
    • one year ago
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    @Rushwr can you help me figure this out?

  3. anonymous
    • one year ago
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    thatd be tight thanks

  4. anonymous
    • one year ago
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    @hartnn

  5. Photon336
    • one year ago
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    @pmkat14

  6. Photon336
    • one year ago
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    Let's take a look at this

  7. Photon336
    • one year ago
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    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|

  8. anonymous
    • one year ago
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    sorry i fugured it out i didnt realize that the oh was attached to a ethyl

  9. anonymous
    • one year ago
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    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?

  10. Photon336
    • one year ago
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    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|

  11. anonymous
    • one year ago
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  12. Photon336
    • one year ago
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    what is your proposed mechanism @pmkat14 ?

  13. anonymous
    • one year ago
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    hold on

  14. anonymous
    • one year ago
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    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

  15. anonymous
    • one year ago
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    donating the e- from the tertiary to the Cl, then the OH-ETH bonds to the tertiary, due to the greater alkyl substituents

  16. anonymous
    • one year ago
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    |dw:1443895351946:dw|

  17. Photon336
    • one year ago
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    @pmkat14 only concern i have is that if the alcohol adds to the side with the (cyclohexyl group) there would be more steric crowding

  18. Photon336
    • one year ago
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    |dw:1443895796846:dw|

  19. Photon336
    • one year ago
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    |dw:1443895913848:dw|

  20. anonymous
    • one year ago
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    that orientation was explained to violate markonvicks rule

  21. anonymous
    • one year ago
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    saying that the electrophile should go to the sp2 carbon with the most hydrogens

  22. anonymous
    • one year ago
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    @Photon336

  23. Photon336
    • one year ago
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    @woodward

  24. Photon336
    • one year ago
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    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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