Q:Why can I not separate naphthalene now?

Even though you have succeeded in separating p-chloroaniline from the original mixture, you still cannot attempt to remove naphthalene.

Naphthalene 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 naphthalene is not achievable when there are still acidic components (benzoic acid and 2-naphthol) present in the mixture.

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