1. How would you separate a mixture of benzoic acid, phenol, and naphthalene? Benzoic acid (pKa = 4.2), phenol (pKa = 10) and naphthalene (pKa is too high for chemically active extraction to be practical) are soluble in organic solvents like methylene chloride or ether, but insoluble in water. A mixture of the three compounds can be separated by a chemically active extraction using two different bases, sodium hydroxide and sodium bicarbonate (NaHCO3). Prepare a flowchart. Write out a series of equations for the acid-base reactions between each of the acids and each of the bases so that you can determine the correct order of steps in your flowchart. Note that naphthalene is neither acidic nor basic enough to participate in a chemically active extraction. You will also need to consider the fact that when bicarbonate ion (HCO3−) accepts a proton, it becomes carbonic acid (H2CO3, pKa 6.4); carbonic acid decomposes immediately to carbon dioxide and water. Recall also that the pKa of water is 15.7.
Please help I am drawing a blank on some steps