Solubility of an Acid: Separating Basic from Acid Compounds

[yungwun22]

Homework Statement

I did an experiment where an extraction was done with an unknown carboxylic sample. Some mass of it was mixed with ether and aqueous NaOH then aqueous layer extracted, etc. The question asks though, why is the unknown compound soluble in aq. base not acid. Also, describe a process by which I would be able to separate a basic compound from an acid compound.

Homework Equations

The Attempt at a Solution

The only answer I can come up with is that there are more available proton acceptors in base allowing for the acid to be ionized and dissolve, but that answer seems too simple and I don't know if my logic is correct. And for the second question I have no idea.

 

[GCT]

You're on the right track , the strong base deprotonates the acid therby increasing its solubility in water , if you know this then you should be able to answer the second question.

 

[symbolipoint]

The salt (anionic carboxylate and the sodium cation) are not soluble in ether; they would be soluble in water. The caboxylic acid, weak acid and mostly protonated, is soluble in ether.