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In this experiment, 0.150 g of a mixture, containing 0.100 g of a neutral unknown compound and 0.050 g of a benzoic acid impurity, is dissolved in 4.0 mL ether. The mixture is extracted two times with 2.0 mL of NaOH ultimately separating the neutral compound and the benzoic acid. Following the extraction 6 M HCl was added to both of the NaOH extracts, resulting in a precipitate. Provide the chemical reaction that occurred when HCl was added. For this reactions use hydronium in place of HCl as that is the active acid. Show all lone pair electrons and formal charges. What does the amount of precipitate in each tube indicate about the extraction procedure?

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