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reaction mixture for 30 min, stirring the mixture rapidly during the process. The start of the reaction is indicated by a slight turbidity of the solution. The mixture may become more turbid as the reaction proceeds and eventually may turn a pale yellow. Allow the reaction mixture to cool to room temperature after the reflux period. Reaction of the Grignard reagent with CO2 :O MgX 1) CO2 (s) 2) HCI OH MgX) magnesium carboxylate complex Grignard reagent substituted benzoic acid Transfer the solution of the Grignard reagent to a beaker and, with stirring, add small pieces of CO2 to the Grignard reagent solution. Stir until all of the CO2 has reacted and then allow the mixture to warm to room temperature. With stirring, add water (~10 mL) followed by aq. 6 M HCl solution (-3 mL) dropwise. Add diethyl ether (-10 mL) and stir the mixture until any remaining solids dissolve. Transfer the two-phase mixture to a separatory funnel and shake vigorously to further extract the product into the organic layer. Isolate the organic layer and extract the aqueous layer with diethyl ether (~5 mL). Combine the organic layers and extract them with aq. 5 % NaOH solution (2x-10 mL portions). Isolate the appropriate layer and acidify with aq. 6M HCl solution. Isolate the solid product by vacuum filtration on a small plastic filter funnel and rinse it with ice- cold water (2 x 5 mL). Allow the product to air-dry-15 min. Report the mass and % yield of the product, and submit samples for 'H-NMR, 'SC-NMR, F-NMR, and HSQC NMR and GC-MS analysis. Obtain an IR spectrum of the dry product. 13.4 Excess Chemical Disposal Transfer any remaining magnesium to the appropriately labelled disposal jar in the fume hood. Pour excess aqueous acid and base solutions into the sink and dilute with tap water. After submitting all necessary NMR/GC-MS/IR samples, transfer the purified carboxylic acid to the