Organic Chemistry Lab I (CHEM 237) Experiment 10: Phase Transfer Catalysis 100% Solved

Organic Chemistry Lab I (CHEM 237) Experiment 10: Phase Transfer Catalysis 100% Solved Objective: To examine the use of a phase transfer catalyst to effect an SN2 reaction in dichloromethane solution. The reaction will be conducted without extraction for product isolation. List the procedural steps, from start to finish, that are required to convert 2-naphthol and allyl bromide into allyl 2-naphthyl ether. - The reaction is performed on a small scale by mixing the alcohol, the haloalkane, and the phase transfer catalyst in a conical vial. Sodium hydoxide (base) is added to initiate the reaction. The reaction flask is covered and stirred to conduct reaction to prevent evaporation of the solvent. The progress of the reaction is monitored by TLC so that no time is wasted. The reaction solution is then dried over calcium chloride to remove any remaining water. The product is purified by column chromatography and collected by evaporation. Match the procedural step to its purpose by dragging each step in the written procedure for the reaction of 2-naphthol with allyl bromide and a phase transfer catalyst in strong base into the appropriate box. - The Williamson ether synthesis between 2-naphthol and allyl bromide in the presence of strong base and benzyltriphenylammonium chloride as a phase transfer catalyst in dichloromethane solution is known to proceed in reasonable yield. Why will the reaction fail to work if the solvent is switched to ethanol while retaining the same reactants, phase transfer catalyst, and base? - Because the base would deprotonate ethanol and create a second nucleophile. The Williamson ether synthesis between 2-naphthol and allyl bromide in the presence of strong base and benzyltriphenylammonium chloride as a phase transfer catalyst in dichloromethane solution is known to proceed in reasonable yield.