How to differentiate phenol, acetic acid, aniline & nitrobenzene

AI Thread Summary
The discussion focuses on identifying the compounds in different layers after sequential chemical treatments of a solution containing phenol, acetic acid, aniline, and nitrobenzene. The initial addition of Na2CO3 results in the formation of two layers, with aniline remaining unreacted, suggesting it is in the aqueous layer A. Following the addition of NaOH to the ethereal layer X, further separation occurs, leading to the formation of aqueous layer B and ethereal layer Y. The final step involves adding dilute HCl, resulting in aqueous layer C and ethereal layer D. Participants emphasize the importance of understanding the pKa values and the acidity or basicity of each compound to accurately identify the layers.
songoku
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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 :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:
 
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songoku said:

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 :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:

Need to see that diagram
 
Start by listing your pKa's for everything and then determine the pH of bicarb solution.
 

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