6. A student prepares ethyl benzoate by the reaction of benzoic acid with ethano

Question

6. 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 purifica tion, you should also use an aqueous sodium bicarbonate solution.

Explanation / Answer

To the reaction mixture aqueous sodium bicarbonate was added slowly up to until the evolution of CO2 gas is ceased. Benzoic acid reacts with sodium bicarbonate to form sodium benzoate with evolution of CO2 and H2SO4 will converted into Sodium Sulfate with evolution of CO2 these two salts are more soluble in water and ethanol also soluble in water.

Then the reaction mixture was taken into a separating funnel extracted several times with solvent like diethyl ether. Salts and EtOH goes to aqeous layer (lower layer because water is more dense than diethyl ether) and org phase was separated and dried with Sodium Sulfate (to remove water ) and solvent was removed under reduced pressure finally we got pure ethyl benzoate

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