Describe how to separate a mixture containing phenol, aniline, benzoic acid, and toluene.

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Expert Solution

Phenol and benzoic acid are acidic, aniline is basic and toluene is an organic neutral compound. Add diethyl ether to the solution. Extract the ether solution with saturated NaHCO₃ solution in water.

The benzoic acid will be converted to sodium benzoate which will dissolve in NaHCO₃ solution. The aqueous layers are separated and acidify it with 5 N HCl converting the sodium benzoate back to benzoic acid.

Extract the remaining ether solution with 3N NaOH to convert the phenol to the sodium salt. Drain the lower aqueous layer and acidify it with 5 N HCl.

The ether layer contains both aniline and toluene. It is treated with 5N HCl; the aqueous layer containing anilinium salt is separated and treated with 3N NaOH to get free aniline.

The organic layer now contains only toluene; gently evaporate the ether (32 ^oC) leaving the toluene (110 ^oC).

queen_honey_blossom answered 4 months ago

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