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Which compound will be extracted in organic layer?

  1. Feb 10, 2016 #1
    I'm having a lot of trouble predicting which compounds would be extracted into which layer (organic vs. aqueous) using acids and bases.

    Using the solvents dichloromethane (which would form the organic layer) and sodium hydroxide (would form the aqueous layer along with water), I am asked to predict which of the following compounds would end up being extracted into the organic layer.

    My predictions for the attached compounds:
    (A) Would be extracted in the AQUEOUS layer.
    NaOH would deprotonate the hydrogen (on the OH) from the bezoic acid, leaving a charged conjugate base.
    Charged materials stay in the aqueous layer.

    (B) Would be extracted in the AQUEOUS layer.
    NaOH would deprotonate the hydrogen (on the OH) from the phenol, leaving a charged conjugate base.
    Charged materials stay in the aqueous layer.

    (C) Would be extracted in the ORGANIC layer.
    NaOH attacks the NH3+ group, forming a neutral compound, and anionic dicyclohexane.
    The neutral compound that forms would be extracted in the organic layer.

    BUT my reasoning seems to be all wrong! The answers state that compounds (A) and (B) will be extracted into the organic layer, but (C) would not be. Why?
     

    Attached Files:

  2. jcsd
  3. Feb 10, 2016 #2

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    A)? Check. B)? Check. C)? Check.
    This could be a "re-cycled" pre-lab that hasn't been proof-read --- who knows.
     
  4. Feb 10, 2016 #3
    Interesting, that's what I was thinking too... so is my reasoning above correct then? Regarding the base being able to deprotonate A and B to form a charged conjugate base; and neutralizing C to form a neutral compound?
     
  5. Feb 10, 2016 #4

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    That's my take.
     
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