Q:Why can I not separate naphthalene now?



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

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 are still an acidic component (2-naphthol) present in the mixture.

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