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Photon336

  • one year ago

The question is: What is the product of the reaction of 2-Hexene with CHCl3 in the presence of potassium tert-butoxide? I chose B: I thought Potassium tert-but oxide is more likely to act as a base. I thought that it pulls the proton off of CHCl3, because the chlorine groups could hold the stabilize the negative charge, and then CHCl3 adds to the double bond. But this idea is wrong..

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  1. Photon336
    • one year ago
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    In case it can't be seen

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  2. Rushwr
    • one year ago
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    I have no Idea but is it the A?

  3. taramgrant0543664
    • one year ago
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    I'm thinking it is B as well but I'm not 100% sure but I know it's not A because that would be the reaction of Cl2 instead of CHCl3

  4. Photon336
    • one year ago
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    @taramgrant0543664 That's exactly what i thought

  5. Photon336
    • one year ago
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    but for whatever reason it's wrong

  6. taramgrant0543664
    • one year ago
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    Do you know which one is right?

  7. aaronq
    • one year ago
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    im pretty sure its D

  8. taramgrant0543664
    • one year ago
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    D was my next thought but I can't picture how that reaction would go

  9. Photon336
    • one year ago
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    This is what I thought of at first

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  10. Photon336
    • one year ago
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    @aaronq @taramgrant0543664 D is correct

  11. Photon336
    • one year ago
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    but I can't see how it would go..

  12. aaronq
    • one year ago
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    its similar to that, CHCl3 gets deprotonated by t-butoxide, then the carbanion attacks the double bond and pushes the electrons to carbon 3, then that carbanion attacks intramolecualry

  13. JoannaBlackwelder
    • one year ago
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  14. Photon336
    • one year ago
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    oooh...

  15. JoannaBlackwelder
    • one year ago
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    Reacting with CHCl3 and a base makes a cyclo.

  16. Photon336
    • one year ago
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    @aaronq okay I see it now, the carbanion attacks the other carbon and removes the chlorine and then creates the cyclic structure.

  17. Photon336
    • one year ago
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    @JoannaBlackwelder to me I always have in my mind that three ring structures are unstable especially if they have large groups attached to them

  18. JoannaBlackwelder
    • one year ago
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    Yeah, true

  19. Photon336
    • one year ago
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    especially with those chlorines that's why i didn't consider that one at first

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