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How to differentiate phenol, acetic acid, aniline & nitrobenzene

  1. Jun 9, 2010 #1
    1. The problem statement, all variables and given/known data
    The question actually contains a diagram but i don't understand how to draw it, so i'll try to describe it in words.
    A solution contains phenol, acetic acid, aniline and nitrobenzene. Na2CO3 is added into the solution and two layers are formed: aqueous layer A and ethereal layer X. Then NaOH is added into ethereal layer X, two layers are formed: aqueous layer B and ethereal layer Y. At last, dilute HCl is added into ethereal layer Y and aqueous layer C and ethereal layer D is formed. The question is, identify the correct combinations of compound A, B, C and D.

    2. Relevant equations

    3. The attempt at a solution
    I am really weak in organic chemistry. I tried to check the characteristics but i don't get it :cry: well, this is my guess: phenol, acetic acid and nitrobenzene is acidic while aniline is alkaline. so when Na2CO3 is added, it will react with those three and leaves aniline unreacted. then A is aniline. then i got confused :confused: i really don't have any idea. and i'm not sure whether my guess is right. help me please.... thanks a lot before..:shy:
  2. jcsd
  3. Jun 9, 2010 #2
    Need to see that diagram
  4. Jun 10, 2010 #3


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    Start by listing your pKa's for everything and then determine the pH of bicarb solution.
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