How to differentiate phenol, acetic acid, aniline & nitrobenzene

[songoku]

Homework Statement

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.

Homework Equations

The Attempt at a Solution

I am really weak in organic chemistry. I tried to check the characteristics but i don't get it 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 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:

 

[gabriels-horn]

Homework Statement

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.

Homework Equations

The Attempt at a Solution

I am really weak in organic chemistry. I tried to check the characteristics but i don't get it 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 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:

Need to see that diagram

 

[chemisttree]

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