Q: Why can I not separate naphthalene now?



Even though you have succeeded in separating both the strong acid (benzoic acid) and the weak acid (2-naphthol) present in 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. As such, separation of naphthalene is not achievable when there is still a basic component (p-chloroaniline) present in the mixture.

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