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To separate a mixture of p-toluic acid and p-toluidine, you can utilize their differing solubilities in an aqueous acid solution. First, dissolve the mixture in a suitable solvent, then add dilute hydrochloric acid; p-toluidine will protonate and dissolve in the aqueous layer as its hydrochloride salt, while p-toluic acid will remain in the organic layer. After separation, you can recover p-toluidine by basifying the aqueous solution, causing it to precipitate out. Finally, p-toluic acid can be isolated by evaporating the organic solvent.

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