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A mixture of benzoic acid and naphthalene was dissolved in tert-butyl methyl ether and the resulting solution was extracted with aqueous sodium bicarbonate. The lower layer was separated and to it was added concentrated hydrochloric acid, upon which a white precipitate formed. What was the structure of the precipitate?

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baraltoa

Answer:

C₆H₅COOH Benzoic Acid

Explanation:

Here we are using the extraction method to separate  benzoic acid from naphtalene in the  ether solution  by reacting it with the base sodium bicarbonate to produce the salt sodium benzoate  ( naphtalene remains in the organic layer )  .

The sodium benzoate  is completely soluble in the aqueous layer being a salt, and  reacts with hydrochloric acid ( again an acid base reaction ) which precipitates the benzoic acid  since the it is insoluble in water hence  separating it.

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