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Draw the reaction mechanism with chemical structures in the separation of naphthalene and benzoic acid by...

Draw the reaction mechanism with chemical structures in the separation of naphthalene and benzoic acid by extraction. 1g of Naphthalene/benzoic acid mixture is dissolved in 15 mL dichloromethane, transferred to a separatory funnel where 10 mL 2.5M NaOH(aq) is added. Organic and Aqueous layers are separated, and 12M HCl(aq) is added to the aqueous layer while cooling, forming a precipitate, which is vacuum filtrated. Don't understand how to draw each chemical structure!

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Answer #1

Benzoic acid and naphthalene are both organic moieties and are soluble in DCM.

On adding 10ml of NaOH, Benzoic acid reacts with NaOH and forms sodium benzoate and becomes water soluble. Hence on adding water, sodium benzoate moves to aqueous layer leaving naphthalene in organic layer.

The layers are separated in separating funnel and then on adding HCl sodium benzoate forms benzoic acid and becomes hydrophobic and gets precipitated as benzoic acid crystals.

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