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Extraction Lab

  1. Nov 30, 2008 #1
    Background:

    Extraction lab using diethyl ether as solvent. Mixed an unknown mixture of benzophenone and salicyclic acid. Try to separate the 2.


    2 Questions:

    1 In separation of ether sol'n from NaOH layer, some of the sol'n was left behind in the ether solution, how would that change the benzophenone recovery? Also indicate the top and bottom layer.

    2 Suggest reasons for low benzophenone recovery .

    My Attempt:

    1. I think benzophenone dissolves in water while the diethyl ether dissolves the acid. If I am right, the diethyl ether should be at the bottom?

    As for the recovery, it would decrease since you would be leaving behind benzophenone in the ether sol

    2. ??? I have no idea except for it evaporating but there should definitely be something important here since everyone got low recovery.

    THANK YOU!
     
  2. jcsd
  3. Nov 30, 2008 #2

    symbolipoint

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    What do you know about those two compounds? What happens when you mix aqueous NaOH solution with a solution containing salicylic ACID? Sodium salts of weak acids are usually soluble in water.
     
  4. Dec 1, 2008 #3
    do u have any ideas on the low benzophenone rxn? I saw this radical rxn on wikipedia for it but I donno if that's right?
     
  5. Dec 1, 2008 #4

    symbolipoint

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    Best guess right now is that no reaction of benzophenone is significant in this extraction. The guess could be wrong. Would enolization occur to benzophenone, and might this influence the extraction process? This is one for the organic chemist members of the forum.
     
  6. Dec 1, 2008 #5

    chemisttree

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    Enolization would require at least one alpha proton. Benzophenone has none and thus no enolization will occur under these conditions.

    The reaction you saw in Wikipedia is for the ketyl of benzophenone and is a free radical. You need an active metal like sodium or potassium to generate it.
     
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