A student prepares ethyl benzoate by the reaction of benzoic acid with ethanol using a sulfuric acid catalyst. The following compounds are found in the crude reaction mixture: ethyl benzoate (major component), benzoic acid, ethanol, and sulfuric acid. Using a handbook, obtain the solubility properties in water for each of these compounds (see Technique 4). Indicate how you would remove benzoic acid, ethanol, and sulfuric acid from ethyl benzoate. At some point in the purification, you should also use an aqueous sodium bicarbonate solution.
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