Q: Why can I not separate 2-naphthol first?

In general, acidic organic compounds are extracted with an aqueous inorganic base such as NaOH. NaOH is a strong inorganic base and both 4-methoxybenzoic acid (a carboxylic acid) and 2-naphthol are ionized to a salt in the presence of NaOH.

	4-Methoxybenzoic Acid C8H8O3 pKa: ~5
	2-naphthol C10H8O pKa: 9.57

Reference: G. Marc Loudon, Organic Chemistry, 3rd ed., Benjamin/Cummings Publishing Co, Inc,

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