The mixture contains benzoic acid, 2-napthol, and naphthalene. Dissolve the mixture in the polar solvent ether. When you react the mixture with 10% NaHCO3(sodium bicarbonatea weak base in aqueous solution) reacts with benzoic acid and forms sodium benzoate an ionic compound (similar to NaCl) that dissolves in aqueous solution (heavier than ether in density) and goes to the bottom of the centrifuge tube or to the bottom of the separatory funnel forming two layers. Then remove the bottom aqueous layer and collect in a beaker labeled as bicarbonate extract. Acidify the bicarbonate extract in the beaker to give benzoic acid. The top ethereal layer contains in the centrifuge tube or separatory funnel 2-napthol and naphthalene. To this top layer add 10% NaOH (sodium hydroxideis a strong base in aqueous solution reacts with only 2-napthol, a weak acid forming 2-napthoxide an ionic compound soluble in aqueous solution (similar to NaCl) that goes to the bottom of the centrifuge tube or to the bottom of the separatory funnel forming two layers. Then remove the bottom aqueous layer and collect in a beaker labeled as hydroxide extract.Acidify the hydroxide extract to give 2-napthol. Left over in the ether solvent is naphthalene. Distill off or evaporate low boiling ether to give naphthalene. What is the atom economy?

Introductory Chemistry: A Foundation

9th Edition

ISBN:9781337399425

Author:Steven S. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Donald J. DeCoste

Chapter15: Solutions

Section: Chapter Questions

Problem 20CR

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The mixture contains benzoic acid, 2-napthol, and naphthalene. Dissolve the mixture in the polar solvent ether. When you react the mixture with 10% NaHCO3(sodium bicarbonatea weak base in aqueous solution) reacts with benzoic acid and forms sodium benzoate an ionic compound (similar to NaCl) that dissolves in aqueous solution (heavier than ether in density) and goes to the bottom of the centrifuge tube or to the bottom of the separatory funnel forming two layers. Then remove the bottom aqueous layer and collect in a beaker labeled as bicarbonate extract. Acidify the bicarbonate extract in the beaker to give benzoic acid. The top ethereal layer contains in the centrifuge tube or separatory funnel 2-napthol and naphthalene. To this top layer add 10% NaOH (sodium hydroxideis a strong base in aqueous solution reacts with only 2-napthol, a weak acid forming 2-napthoxide an ionic compound soluble in aqueous solution (similar to NaCl) that goes to the bottom of the centrifuge tube or to the bottom of the separatory funnel forming two layers. Then remove the bottom aqueous layer and collect in a beaker labeled as hydroxide extract.Acidify the hydroxide extract to give 2-napthol. Left over in the ether solvent is naphthalene. Distill off or evaporate low boiling ether to give naphthalene. What is the atom economy?

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