Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline.

Extraction is the process of separating compounds present in the mixture. One is solvent extraction, in which solvents are separated based on their solubilities. This process is also used to isolate solute from reaction solvent.

At first, a mixture of compounds (benzoic acid, phenol, benzyl alcohol and aniline) is shaken with ether and HCl (aq). With ether, benzoic acid, phenol and benzyl alcohol are separated from the mixture and with HCl (aq), PhNH₃⁺Cl^-is formed. Benzoic acid, phenol, and benzyl alcohol are shaken with aqueous sodium bicarbonate. With ether, a mixture of phenol and benzyl alcohol is separated. With sodium bicarbonate,PhCOO^-Na⁺ is formed. Then, a mixture of phenol and benzyl alcohol is shaken with aq. NaOH. There forms benzyl alcohol with ether and PhO^-Na⁺ with aq. NaOH is separated.

On evaporating, pure benzyl alcohol is formed. WhenPhO^-Na⁺ is shaken with ether and HCl (aq). With HCl (aq), NaCl is formed, and with ether, phenol is formed. This phenol, when evaporated, results in the formation of pure phenol.

Now,PhCOO^-Na is shaken with ether and HCl(aq). With HCl, NaCl is formed, and with ether, is formed. This PhCOOH is evaporated to form pure PhCOOH.

WhenPhNH₃⁺Cl^- is shaken with NaOH (aq) and ether, then with NaOH, NaCl is formed, and with ether,PhNH₂ (aniline) is formed. This aniline, when evaporated, it forms a pure aniline compound. Thus, in this way, the mixture of compounds is separated.

The flow diagram given below shows the separation of the mixture of compounds,

Separation of a mixture of compounds