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Interesting inter-conversions of carbon compounds

  1. Aug 25, 2015 #1
    1. The problem statement, all variables and given/known data
    CH2=CHCHCH3 + X --> CH3CHClCH2CH3

    CH3CHClCH2CH3 + KOH(aq) --> Y
    then what is the structural formular of Y ?? (show clearly where the functional group located)


    3. The attempt at a solution
    It is obvious that X is HCl, and Y should be an alcohol but where is the hydroxyl group be attached and why????
     
    Last edited: Aug 25, 2015
  2. jcsd
  3. Aug 25, 2015 #2

    Borek

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    Staff: Mentor

  4. Aug 25, 2015 #3
    can you draw the structural formular for me?? I am really confused
     
  5. Aug 25, 2015 #4
    My answer is 2-methylpropanol but someone told me that it is butan-1-ol which one is correct???
     
  6. Aug 25, 2015 #5

    Borek

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    Why do you think the straight chain of the original alkene gets rearranged?
     
  7. Aug 25, 2015 #6
    As OH group will replace the chlorine atom in the second carbon atom (counted from the left)as written in the question
    Correct or not???
     
    Last edited: Aug 25, 2015
  8. Aug 25, 2015 #7

    Borek

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    Yes, OH replaces the Cl. But why do you think it ends with the conversion of a straight C-C-C-C chain to a branched one?
     
  9. Aug 25, 2015 #8
    As CH3CHClCH2CH3 is changed to CH3CH(OH)CH2CH3

    Oh my mistake!!!!!!!!!!!!!!!!!!!!
    is the answer butan-2-ol?????
     
    Last edited: Aug 25, 2015
  10. Aug 25, 2015 #9

    Borek

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    Looks like.
     
  11. Aug 27, 2015 #10

    Merlin3189

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    Can a non-chemist just query a couple of points please?

    In the OP
    On the LHS it looks to me like the third C should have another H ? And if X is HCl, there seems to be one H short on the LHS? ( C4H7 +HCl -> C4H9Cl )

    In Borek's first response, Markovnikov's rule seems to tell us where the Cl gets substituted, which is not the question? The position of the Cl seems to be shown already in the second equation and the question seems to be, where does the OH get put when it substitutes for the Cl. In my naivety, I simply guessed the OH would go in the same place as the Cl, but does Markovnikov have something to say about it?
    When I looked it up (I didn't know it) it seemed to apply to A-C=C-B + HX situations. But in the second reaction, the double bond is already gone and we're looking at P-CCl-Q + OH-
     
  12. Aug 27, 2015 #11

    Borek

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    Yep, the equation was a little bit lousy.

    Yes, but that's actually the only thing that matters here, as the next step is just an SN reaction in which (as you correctly assumed) -OH replaces -Cl. So the final product is defined by the way HCl reacts with the double bond.
     
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