Based on their acid and base properties, naphthalene, benzoic acid and ethyl 4-aminobenzonate mixed in ether solution could be separated using separation funnel. One student initially used HCl solution for this separation. Which compound he may find in the lower layer upon the addition of HCl solution

See explanation

Explanation:

When using a separating funnel to separate a mixture of substances, we expect that the system will consist of an organic phase and an aqueous phase. The organic phase is usually found on top while the aqueous phase is found below.

When naphthalene, benzoic acid and ethyl 4-aminobenzonate mixed in ether solution is separated using HCl, the ethyl 4-aminobenzonate is found in the lower aqueous layer.

This is because, the ethyl 4-aminobenzonate can react with HCl to form an ionic hydrochloride salt which dissolves in the lower aqueous layer.

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