Procedure

           A hot plate was turned on and set to 250 °C. Cyclohexanol (2.0 grams, 20 mmol) was pipetted into a 5 mL round-bottomed (RB) flask RB flask. A buret was used to add phosphoric acid (0.5 mL, 9 mmol) to the RB flask. Boiling chips were added to the RB flask. A fractional distillation was performed on the liquid mixture inside the RB flask at a rate of one drop every 20-30 seconds. The temperature was recorded at the time of the first drop, and again once every four drops after that. The distillate was collected at 68°C. The liquid mixture was distilled until approximately 10% of the original volume remained in the flask. The contents of the collection vial were pipetted into a test tube, and a work-up was performed. The mixture was washed by adding 1 mL of water to the test tube, mixing thoroughly, and removing the lower, aqueous layer. This process was repeated with 1 mL of NaOH and 1 mL of NaCl. The contents of the test tube were pipetted to a new vial. Several CaCl2 spheres were added to the vial until the CaCl2 spheres no longer clumped together. After being transported to a third and final vial, the mass of the liquid was recorded. Samples were taken of the liquid to be analyzed by gas chromatography and infrared spectroscopy. With the remaining contents of the vial, two chemical tests were performed. First, 0.5 mL of cyclohexene product was added to one vial, and 0.5 mL of cyclohexane was added to a second vial. Three to four drops of bromine in dichloromethane was added to both vials and the resulting color changes were recorded. Finally, 0.3 mL of cyclohexene were added to one vial and 0.3 mL of cyclohexane were added to a second vial. Two to three drops of potassium permanganate were added to both vials and the resulting color changes were recorded.