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?

Explanation:

Sodium benzoate forms when benzoic acid reacts with sodium bicarbonate. Since benzoic acid is readily soluble in ether than water, the salt of benzoic is more soluble in water than in ether because it is ionic and very polar. water which is the lower layer will contain sodium benzoate.

After separating the lower layer, if acidified with Hcl,benzoic acid will be regenerated, it precipitates out as a result of its low solubility in water.