How does acetone (polar solvent) pull freebase from Na2CO3?

[dogsoldier]

I am planning my first extraction: vinegar simmer -> lye -> toluene -> vinegar wash -> sodium carbonate -> acetone -> evap over leaf
I think I understand everything except the final pull: we will put the acetates into the sodium carbonate in order to basify them, which makes them non-polar, but then how does the acetone pull them out, since acetone is a polar solvent?
Thank you!

 

[Jagube]

Acetone dissolves both polar and non-polar solutes, because it has both polar and non-polar parts.
It has two methyl groups, which are non-polar, but it also has a polar carbonyl (C=O) group, which can solvate more polar compounds.

 

[dogsoldier]

Acetone dissolves both polar and non-polar solutes, because it has both polar and non-polar parts.
It has two methyl groups, which are non-polar, but it also has a polar carbonyl (C=O) group, which can solvate more polar compounds.

Interesting! Why can't we use acetone for the initial pulls from the lye soup then?

 

[Jagube]

Interesting! Why can't we use acetone for the initial pulls from the lye soup then?

Acetone is miscible with water. This is due to its polar group, which creates hydrogen bonds with water.

The lye soup is an aqueous system. If you add acetone to it, it will mix with the water, which will make it impossible to pull anything. To pull anything you need two separate layers (e.g. two liquids, or a liquid and solids).

You can only pull with acetone from dry material, which is what you do in the second pull stage, after the sodium carbonate basing. If your acetone is not anhydrous (i.e. free from water), it will pick up some of the sodium carbonate, as well as sodium acetate (resulting from the neutralization reaction of the sodium carbonate with the acetic acid) and whatever other water-soluble things might be in there.

P.S. I'm not a chemist and I'm only learning and trying to understand this, so those more knowledgeable please feel free to correct me.

 

[dogsoldier]

Interesting! Why can't we use acetone for the initial pulls from the lye soup then?

Acetone is miscible with water. This is due to its polar group, which creates hydrogen bonds with water.

The lye soup is an aqueous system. If you add acetone to it, it will mix with the water, which will make it impossible to pull anything...

Of course, the water! Thanks man, I'm ready to roll now!