Is extraction based on solubility or polarity?

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virtualmaster999

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Hi all!

Chad's says polarity...but BC says solubility. So does KBB.

So solubility then??

Thanks in advance!!

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Hi all!

Chad's says polarity...but BC says solubility. So does KBB.

So solubility then??

Thanks in advance!!

Recall that polar substances tend to dissolve in polar solvents, and nonpolar substances dissolve in nonpolar solvents. Thus Polarity AFFECTS solubility.

The best answer to your question in that Extraction is based on solubility. However,both are related. Instead of playing this game of semantics, it is more important that you understand the principles.

If you were to separate 4 compounds.....Phenol, Toluene, Benzoic acid and Aniline, what would you do ?

Ok.....lets make a move......all 4 are dissolved in THF solvent. If we add NaHCO3.....we can separate out the benzoic acid as sodium benzoate by bringing it into the aqueous layer. Treatment by acid can isolate the benzoic acid.

Now we have 3 compounds left. NaOH treatment can bring the phenol into the aqueous layer as the phenoxide salt, and once again acid treatment gives the isolated phenol. Now with 2 left.....a strong acid like HBr brings the amine, aniline, into the aqueous layer to give the ammonium salt. Addition of base, yields aniline in isolation. We are now left with toluene and THF......which can be evaporated.

The importance of extraction is something that might come in handy some day !!!!

I hope this helps.

Dr. Jim Romano
 
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I think it is pretty much the same. Like dissolves like. So polar / charged things would be in the aqeuous layer or something like that while nonpolar in the organic?
 
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Recall that polar substances tend to dissolve in polar solvents, and nonpolar substances dissolve in nonpolar solvents. Thus Polarity AFFECTS solubility.

The best answer to your question in that Extraction is based on solubility. However,both are related. Instead of playing this game of semantics, it is more important that you understand the principles.

If you were to separate 4 compounds.....Phenol, Toluene, Benzoic acid and Aniline, what would you do ?

Ok.....lets make a move......all 4 are dissolved in THF solvent. If we add NaHCO3.....we can separate out the benzoic acid as sodium benzoate by bringing it into the aqueous layer. Treatment by acid can isolate the benzoic acid.

Now we have 3 compounds left. NaOH treatment can bring the phenol into the aqueous layer as the phenoxide salt, and once again acid treatment gives the isolated phenol. Now with 2 left.....a strong acid like HBr brings the amine, aniline, into the aqueous layer to give the ammonium salt. Addition of base, yields aniline in isolation. We are now left with toluene and THF......which can be evaporated.

The importance of extraction is something that might come in handy some day !!!!

I hope this helps.

Dr. Jim Romano
Thanks Dr. Romano! I can see how the semantics makes a difference, but it is nice to see the concept laid out like this!
 
I think it is pretty much the same. Like dissolves like. So polar / charged things would be in the aqeuous layer or something like that while nonpolar in the organic?
I hope if I get a question like this they wont have polarity and solubility as an option!
 
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