Synthesis of Cyclohexene via Dehydration of Cyclohexanol Procedure

Cyclohexanol (1.99 g, 19.8 mmol) was measured into a 5mL round-bottomed (rb) flask.  85% phosphoric acid (0.5 mL) was added to the rb flask.  The system was heated and the product was collected through fractional distillation.  The temperature plateau occurred at 64 °C and the product was obtained in a collection vial.  The product was transferred to a reaction tube.  The reaction tube was washed with water (1 mL).  The procedure was repeated with sodium hydroxide (1 mL) followed by saturated sodium chloride (1 mL).  The product was then dried with calcium chloride pellets (5 min).  The remaining product yielded (0.77 g, 47%).  The product was tested for the compounds it contained with infrared spectroscopy and gas chromatography (one peak) with a retention time (RT) of 0.435.  A bromine solution was added drop-wise to (0.5 mL) of the product and the prescence of cyclohexene was indicated by a color change of the bromine from reddish-orange to colorless.  A potassium permanganate reagent was added drop-wise to (0.3 mL) of the product and the presence of cyclohexene was indicated by a color change from purple to clear with a dark brown precipitate.  These tests were then compared to cyclohexane, which did not react with the reagents.