Acid–base extraction
A mixture of benzoic acid and naphthalene in diethyl ether is shaken with aqueous NaOH. Where does the benzoic acid end up?
Answer B: explanation for every choice
A
The deprotonated acid is ionic and leaves the nonpolar ether layer.
B
Correct. NaOH deprotonates the acid, forming a charged salt that dissolves in water.
C
Sodium benzoate is water-soluble, so it does not precipitate.
D
Naphthalene is neutral and nonpolar, so it stays in the ether layer.
TakeawayDeprotonated acids and protonated bases move into water. Neutral compounds stay in the organic layer.
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Reviewed 2026-11-05 by a medical student. Spot an error? Report it with question ID cp50.