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Oxidation of Benzhydrol

  1. Mar 2, 2016 #1
    In a lab we oxidized benzhydrol to produce benzophenone. We use glacial acetic acid and sodium dichromate dehydrate to oxidize the benzhydrol. Then we set up the first extraction with water and CH2Cl2 and the second with NaHCO3 and CH2Cl2.

    I am trying to figure out what all of the chemicals used are doing.
    Especially what the glacial acetic acid is doing?
    I am also not quite getting the purpose of the NaHCO3.

    I believe that the dichromate is a catalyst that produces a complex with the benzhydrol.
    I can't figure out what the acid is doing. My major barrier is that I thought that the lab was trying to remove the hydrogen from the benzhydrol (oxidize it) and wouldn't the acid get in the way of this since it is all to willing to give up its proton (I am guessing more so then the benzhydrol).
    [PLAIN]http://://o.quizlet.com/mXl.vLVhNjF3Y6JD7WMDyg_m.png [Broken] [Broken]
    [PLAIN]http://://o.quizlet.com/mXl.vLVhNjF3Y6JD7WMDyg_m.png [Broken] [Broken]
     
    Last edited by a moderator: May 7, 2017
  2. jcsd
  3. Mar 2, 2016 #2

    Borek

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    Staff: Mentor

    Hint: converting an alcohol to a ketone is just an oxidation.
     
  4. Mar 2, 2016 #3
    Totally get that this conversion is oxidation. I was wondering why I would put something in the reaction put that would be more likely to undergo a loss of a proton over the alcohol. In another experiment we utilized glacial acetic acid and NaOCl. The purpose of the acid there is to react with the OCl making the hypochlorous acid that then undergoes an addition reaction with the alcohol. Then the alcohol hydrogen is taken by water and then the carbon's hydrogen is taken by another water. Then the chlorine leaves and a ketone is formed. I am still not getting the dichromate and glacial acetic acid's relation.
     
  5. Mar 3, 2016 #4

    Borek

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    Staff: Mentor

    If it is an oxidation - does the dichromate play a role of a catalyst?
     
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