Katrina Markussen 4/13/2011 Kathleen Kolbet

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Experimental Section Procedure: Experiment One: Preparation and Distillation of Cyclohexene. Added 7.70 ml of cyclohexanol and 1.8 ml of phosphoric acid to flask. Fitted flask to fractional distillation apparatus. Heating reaction mixture to reflux, collecting distillate until volume in flask is about 1ml. Workup: Transferred distillate to funnel and washed with about 4ml of water. Separated layers and transferred organic layer into flask. Added sodium sulfate to distillate to dry. Collected distilled organic material, boiling range: 68C-90C. Experiment two: Synthesis of Adipic Acid. Added 0.5479g of Sodium tungstate dehydrate, 0.5415g of Aliquat 336, 11.9262g of Hydrogen peroxide, 0.3674g Potassium bisulfate, and 2.1500g of Cyclohexene all to flask. Fitted to condenser on sandbath and stirred vigorously for an hour and a half. Pipetted hot reaction mixture leaving behind transfer catalyst. Cooled beaker in ice bath to form precipitate. Collected crude product using vacuum filtration. Weighed and determined melting point to be . Results: Experiment One: Preparation and Distillation of Cyclohexene 1 C6H120+ 1 H3PO4 Reactants: Cyclohexanol: molar mass: 100.158g/mol; volume used: 7.70 ml; boiling point: 160.84C; melting point: 25.93C; density: 0.962 g/mL; hazards: flammable. Phosphoric acid: molar mass: 98.00 g/mol; volume used: 1.8 mL; boiling point: 158C; melting point: 42.35C; density: 1.885 g/mL; hazards: corrosive. Product: Cyclohexene: molar mass: 82.143 g/mol; theoretical yield: 7.411692g; actual yield: 2.7442g; percent yield: 37%; (literature) boiling point: 82.98C; (literature) melting point: -103.5C; density: 0.8110 g/cm3; recorded boiling range: 68C- 90C. C6H10

Experiment two: Synthesis and Recrystallization of Adipic Acid. Chem eq Reactants: Sodium tungstate dehydrate: molar mass: 329.85 g/mol; mass used: 0.5479g; boiling point: n/a; melting point: 698C; density: 4.179 g/cm3; hazards: fireproofing agent. Aliquat 336(catalyst): molar mass: 404.16 g/mol; mass used: 0.5415g; boiling point: 225C; melting point: -20C; density: 0.884g/mL; hazards: harmful if inhaled. 30% Hydrogen Peroxide: molar mass: 34.01 g/mol; mass used: 11.9262g; boiling point: 108C; melting point: -25C