Q: Why can I not separate acetanilide now?

Even though you have succeeded in separating 4-bromoaniline from the original mixture, you cannot remove acetanilide yet.

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 is an acidic component (benzoic acid) present in the mixture.

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