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please draw a detailed mechanism for this experiment ( include curve arrows): We

ID: 920826 • Letter: P

Question

please draw a detailed mechanism for this experiment ( include curve arrows):

Weigh a dry 50 mL round bottom flask and dissolve 5 g of benzoic acid in 15 mL of methanol in the flask. Place a magnetic stir bar into the flask and clamp the flask above a stirrer in the fume hood. Very slowly, add 1.0 mL concentrated sulfuric acid to the reaction flask while stirring. Fit the flask with a reflux condenser and, using a heating mantle, reflux the solution gently for 60 minutes. Cool the solution to room temperature and transfer the contents to a separatory funnel containing 25 mL water. Rinse the reaction flask with about 25 mL of dichloromethane and add this to the separatory funnel. Draw off the aqueous phase and set aside. Wash the organic phase with 25 mL water, then 25 mL 5% NaHCOs solution, and finally with 20 mL saturated NaCl solution. Set the organic layer aside in a labeled beaker. Combine aqueous phases and acidify with dropwise addition of concentrated hydrochloric acid. When sufficient acidity is established, unreacted benzoic acid will precipitate out. Isolate unreacted benzoic acid by suction filtration, washing the filter cake with cold H^O. Leave the crystals to dry until the end of the lab period, and record their mass. You will need this value for K_eq calculations. Transfer the organic phase to a pre-weighed 100 mL round bottom flask, and distill off the solvent (and traces of water) until all that remains is your ester.

Explanation / Answer

please draw a detailed mechanism for this experiment ( include curve arrows): We