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Reaction mechanism

  1. Jun 10, 2008 #1
    1. The problem statement, all variables and given/known data

    Draw a step-by-step mechanism using curly arrows for the following transformation. You do not have to worry about stereochemistry of the final product.

    2. Relevant equations

    None

    3. The attempt at a solution

    [​IMG]

    So the reaction is shown in the diagram in the first line. Here's what I did:

    1. Electrons in the O-H bond move toward the oxygen, and hydrogen gets detached, forming a negative charge on the oxygen
    2. pi electrons from the double bond attack a H+ (from the acid) and forms a carbocation
    3. The negative oxygen's electrons are attracted to the carbocation centre and draws the molecule into a ring formation

    Does the mechanism make sense? Are there any other better ways of doing it? I know that there's another mechanism that involves the water molecule coming in, but I'm not sure about it.


    Thanks
     
  2. jcsd
  3. Jun 11, 2008 #2

    Borek

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    Staff: Mentor

    How likely is the presence of O- if it happens in the sulfuric acid?
     
  4. Jun 11, 2008 #3

    chemisttree

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    When I examine reaction mechanisms and am given a catalyst (like H2SO4 in this case), I try to use it in the first step. In this case H+ is the catalyst.
     
  5. Jun 11, 2008 #4
    Hm... I attempted it again, using your suggestions, and here's my result.

    [​IMG]

    Does that look better?
     
  6. Jun 11, 2008 #5

    chemisttree

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    That's close. I wouldn't have lost the primary alcohol. If the alcohol were labelled (as O-18), the label would probably be found in the product.
    Also, the sulfuric acid probably adds across the double bond in Markovnikov fashion.
     
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