The experiment was about separating acids and neutral compounds by solvent extraction.
Question: If you mistakenly extracted the ether solution of the mixture with NaOH first and then with NaHCO3, what would happen? Briefly explain in a short paragraph. The three compounds in the mixture used were p-toluic acid (pKa=4.2, strong acid), p-tert butyl phenol (pKa=10.2, weak acid), and acetanilide (pKa=20, neutral).