You are missing a step where you add any reagent with a nitro group in it at all.
What is the standard way of nitrating a aromatic compound? (i.e. list of reagents for this reaction?)
oh sorry. the nitrating mixture was forming a No2+ by adding HNO3 to H2SO4. acetic acid added to acetanilide (acetanilide used as the CH3C=O group protects the amine group when adding nitrating mixture) then add conc H2SO4 Then the nitrating mixture is added. Then the whole mixture is added to ice water, p-nitroacetanilide precipitates? Filter and dissolve p-nitroacetanilide in water Add Conc HCL Reflux in condenser till a orange solution Add Base (conc NH3) to precipitate p-nitroaniline filter and Recrystallize to get pure p-nitroaniline (and a by product of ortho-nitroaniline?)
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Forum Rules, You must provide us with your answers as you think they might be . We are happy to assist after that. -Zack
I thought I gave my ideas after every question? First the question was the function of acetic acid. I only know it as a solvent. Are there any special features of acetic acid for it to be chosen as a solvent?
Next they asked what is the function of Adding sulphuric acid to the acetanilide/acetic acid solution(note I havnt added the nitrating mixture yet. The nitrating mixture was prepared by adding HNO3 to H2SO4.) I can only think of it as to increase the melting point of the mixture? as glacial acetic acid has very low melting point at 16 degree Celsius.
After adding nitrating mixture and left for the reaction to finish, ice water is added. And they asked for the purpose of ice water. Really stuck here. Don't really know why the product precipitates upon adding ice water. I am guessing something to do with the NO2- functional group?
Finally, the HCL that is added during hydrolysis of the amide functional group. I know it is to cleave off the amide bonds but I don't get how.
You are missing a step where you add any reagent with a nitro group in it at all.
What is the standard way of nitrating a aromatic compound? (i.e. list of reagents for this reaction?)
oh sorry. the nitrating mixture was forming a No2+ by adding HNO3 to H2SO4. acetic acid added to acetanilide (acetanilide used as the CH3C=O group protects the amine group when adding nitrating mixture) then add conc H2SO4 Then the nitrating mixture is added. Then the whole mixture is added to ice water, p-nitroacetanilide precipitates? Filter and dissolve p-nitroacetanilide in water Add Conc HCL Reflux in condenser till a orange solution Add Base (conc NH3) to precipitate p-nitroaniline filter and Recrystallize to get pure p-nitroaniline (and a by product of ortho-nitroaniline?)
Quote from:
Forum Rules, You must provide us with your answers as you think they might be . We are happy to assist after that. -Zack
I thought I gave my ideas after every question? First the question was the function of acetic acid. I only know it as a solvent. Are there any special features of acetic acid for it to be chosen as a solvent?
Next they asked what is the function of Adding sulphuric acid to the acetanilide/acetic acid solution(note I havnt added the nitrating mixture yet. The nitrating mixture was prepared by adding HNO3 to H2SO4.) I can only think of it as to increase the melting point of the mixture? as glacial acetic acid has very low melting point at 16 degree Celsius.
After adding nitrating mixture and left for the reaction to finish, ice water is added. And they asked for the purpose of ice water. Really stuck here. Don't really know why the product precipitates upon adding ice water. I am guessing something to do with the NO2- functional group?
Finally, the HCL that is added during hydrolysis of the amide functional group. I know it is to cleave off the amide bonds but I don't get how.
I think the aceit acid is chosen as a solvent because the sulfuric acid might deprotect the amide protecting group. By using acetic acid as a solvent you move the equilibrium to the protected aniline. Just a guess..
I think the aceit acid is chosen as a solvent because the sulfuric acid might deprotect the amide protecting group. By using acetic acid as a solvent you move the equilibrium to the protected aniline. Just a guess..
You are missing a step where you add any reagent with a nitro group in it at all.
What is the standard way of nitrating a aromatic compound? (i.e. list of reagents for this reaction?)
You are missing a step where you add any reagent with a nitro group in it at all.
What is the standard way of nitrating a aromatic compound? (i.e. list of reagents for this reaction?)
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-Zack
-Zack
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oh sorry. the nitrating mixture was forming a No2+ by adding HNO3 to H2SO4.
acetic acid added to acetanilide (acetanilide used as the CH3C=O group protects the amine group when adding nitrating mixture)
then add conc H2SO4
Then the nitrating mixture is added.
Then the whole mixture is added to ice water, p-nitroacetanilide precipitates?
Filter and dissolve p-nitroacetanilide in water
Add Conc HCL
Reflux in condenser till a orange solution
Add Base (conc NH3) to precipitate p-nitroaniline
filter and Recrystallize to get pure p-nitroaniline (and a by product of ortho-nitroaniline?)
Quote from:
I thought I gave my ideas after every question?
First the question was the function of acetic acid. I only know it as a solvent. Are there any special features of acetic acid for it to be chosen as a solvent?
Next they asked what is the function of Adding sulphuric acid to the acetanilide/acetic acid solution(note I havnt added the nitrating mixture yet. The nitrating mixture was prepared by adding HNO3 to H2SO4.) I can only think of it as to increase the melting point of the mixture? as glacial acetic acid has very low melting point at 16 degree Celsius.
After adding nitrating mixture and left for the reaction to finish, ice water is added. And they asked for the purpose of ice water. Really stuck here. Don't really know why the product precipitates upon adding ice water. I am guessing something to do with the NO2- functional group?
Finally, the HCL that is added during hydrolysis of the amide functional group. I know it is to cleave off the amide bonds but I don't get how.
Thanks for reading
oh sorry. the nitrating mixture was forming a No2+ by adding HNO3 to H2SO4.
acetic acid added to acetanilide (acetanilide used as the CH3C=O group protects the amine group when adding nitrating mixture)
then add conc H2SO4
Then the nitrating mixture is added.
Then the whole mixture is added to ice water, p-nitroacetanilide precipitates?
Filter and dissolve p-nitroacetanilide in water
Add Conc HCL
Reflux in condenser till a orange solution
Add Base (conc NH3) to precipitate p-nitroaniline
filter and Recrystallize to get pure p-nitroaniline (and a by product of ortho-nitroaniline?)
Quote from:
I thought I gave my ideas after every question?
First the question was the function of acetic acid. I only know it as a solvent. Are there any special features of acetic acid for it to be chosen as a solvent?
Next they asked what is the function of Adding sulphuric acid to the acetanilide/acetic acid solution(note I havnt added the nitrating mixture yet. The nitrating mixture was prepared by adding HNO3 to H2SO4.) I can only think of it as to increase the melting point of the mixture? as glacial acetic acid has very low melting point at 16 degree Celsius.
After adding nitrating mixture and left for the reaction to finish, ice water is added. And they asked for the purpose of ice water. Really stuck here. Don't really know why the product precipitates upon adding ice water. I am guessing something to do with the NO2- functional group?
Finally, the HCL that is added during hydrolysis of the amide functional group. I know it is to cleave off the amide bonds but I don't get how.
Thanks for reading
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Just a guess..
Just a guess..
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