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Carboxylic acids and phenols can be separated by chemically active extraction if the pH of the aqueous layer is properly chosen. Phenols are sufficiently acidic to be extracted into aqueous sodium hydroxide, but not into aqueous sodium bicarbonate, while the more acidic carboxylic acid can be extracted into aqueous sodium bicarbonate. Amines can be extracted from organic solvents by dilute aqueous acid because of the formation of polar ammonium salts. Construct a detailed flow diagram showing how you would separate a mixture of benzoic acid, p-bromophenol, aniline, and naphthalene.

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