Q: Why can I not separate acetanilide now?



Acetanilide is the neutral compound in the mixture. Since it is neutral, it will not react with any inorganic base or acid. There are no sites available for ionization, a critical requirement for solubility in the aqueous phase. Separation of acetanilide is not achievable when there are acidic (benzoic acid) and basic (4-bromoaniline) components present in the mixture.

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Organic Web Chem University of Alberta