You might separate a mixture of aniline, p-cresol, benzoic acid, and toluene using ordinary laboratory reagents. 1. dissolving the mixture in a water-immiscible organic solvent - NaHCO3, H2O, CH2Cl2 2. dissolving the mixture in a water-immiscible organic solvent - NaOH, H2O, CH2Cl2 3. dissolving the mixture in a water-immiscible organic solvent - H3O+Cl-, H2O, CH2Cl2 What component extracts with aqueous acids or bases on each step?

1. benzoic acid

2. p-cresol

3. Aniline

Explanation:

1. Dissolving the mixture in a water-immiscible organic solvent - NaHCO₃, H₂O, CH₂Cl₂:

Only benzoic acid will react with the base, sodium bicarbonate and will form ionic salt which is soluble in the water and thus benzoic acid acids gets separated in the aqueous medium.

2. Dissolving the mixture in a water-immiscible organic solvent - NaOH, H₂O, CH₂Cl₂:

p-cresol will react with strong base NaOH and form a salt with sodium ions which is soluble in water and thus p-cresol gets separated in the aqueous medium.

3. Dissolving the mixture in a water-immiscible organic solvent - H₃O⁺Cl⁻, H₂O, CH₂Cl₂:

Aniline will react with H₃O⁺Cl⁻ and form salt, anilinium chloride which is soluble in water and thus aniline gets separated in the aqueous medium.

Toulene will remain in the organic layer.