Isolation of phenol

OK, Let's isolate phenol* from the solution which contains it.

A basic aqueous solution contains the sodium salt* of phenol, sodium phenolate*.

You want to change sodium phenolate (salt of a weak organic acid) to the water-insoluble phenol (weak organic acid) by converting the salt to a protonated*, non-ionic* form.

Which solution will you add?

5% HCl
5% NaOH
conc. HCl
conc. NaOH

Organic Web Chem University of Alberta