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OChem Issue: Tosylation

  1. Jan 17, 2015 #1
    1. The problem statement, all variables and given/known data

    Predict the major product in the following reaction (Hint: Consider intra-molecular reaction)

    2. Relevant equations

    HO2C-(CH2)3-CH(OH)-CH3 ------------cat. p-TsOH, heat----------> ???

    3. The attempt at a solution

    Essentially what I cannot figure out is if the tosic acid is going to replace the -OH group of the carboxylic acid, the other standalone -OH group, or both. I would assume that it would only replace one since the molecule would likely be more stable, and for that same reason I would also assume that it would replace the 2 prime -OH rather than the -OH attached to the carboxylic acid group.
     
  2. jcsd
  3. Jan 17, 2015 #2

    A screenshot of the molecule in Marvin Sketch is attached
     

    Attached Files:

  4. Jan 18, 2015 #3

    Bystander

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    And, your doubts regarding your assumption are what?
     
  5. Jan 18, 2015 #4
    My original thought was stability, but I am not sure. We were never shown an example problem where there was any more than one -OH group in class, nor were we shown what could happen if there are two oxygen-centric functional groups. I just do not know how to go about dealing with them since we only worked one or two problems with run-of-the-mill 1 and 2 prime alcohols.
     
  6. Jan 18, 2015 #5

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    The second "-OH" group you're worried about doesn't work as such; it's part of the carboxylic acid functional group and has to be treated as being part of that group rather as another alcohol group. Feel a little more comfortable?
     
  7. Jan 18, 2015 #6
    Extremely, thank you. I was mainly unsure of that exact point. "Is is still treated as a lone hydroxyl group, or is it treated as a part of a group that does not necessarily obey that tosylate rule?" That clears everything up.
     
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