How to differentiate phenol, acetic acid, aniline & nitrobenzene

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SUMMARY

The discussion focuses on the separation and identification of phenol, acetic acid, aniline, and nitrobenzene using sodium carbonate (Na2CO3) and sodium hydroxide (NaOH). The user hypothesizes that aniline remains unreacted when Na2CO3 is added, leading to its identification as aqueous layer A. The process involves multiple layers formed through the addition of NaOH and dilute HCl, resulting in distinct aqueous and ethereal layers. The final identification of compounds in layers B, C, and D requires further analysis of pKa values and solution pH.

PREREQUISITES
  • Understanding of organic chemistry fundamentals, specifically acid-base reactions.
  • Knowledge of pKa values for phenol, acetic acid, aniline, and nitrobenzene.
  • Familiarity with liquid-liquid extraction techniques.
  • Basic skills in interpreting chemical reactions and layer formation in solutions.
NEXT STEPS
  • Research the pKa values of phenol, acetic acid, aniline, and nitrobenzene.
  • Learn about liquid-liquid extraction methods and their applications in organic chemistry.
  • Study the effects of sodium carbonate and sodium hydroxide on organic compounds.
  • Explore the principles of acid-base chemistry to understand layer formation in solutions.
USEFUL FOR

Students studying organic chemistry, particularly those focusing on separation techniques and acid-base reactions, as well as educators looking for practical examples of compound differentiation.

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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