Which compound remains in the ether and which compound


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. Which compound remains in the ether and which compound moves to the aqueous NaOH? Provide the chemical reaction that occurred when NaOH was added. Show all lone pair electrons and formal charges. Clearly indicate the difference between an ionic bond and a covalent bond.

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Chemistry: Which compound remains in the ether and which compound
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