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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