Experiment 7- Dehydration of Cyclohexanol

• Use 8 ml of cyclohexanol (instead of 5 ml)

• Use 2.5 ml of 85% phosphoric acid (syrupy concentrated form) instead of 9M

sulfuric acid; careful, corrosive acid!

• Set up a fractionation column for this experiment but leave it empty (i.e., no glass
beads needed)

Procedure Summary:

1. Place a stir bar, 8 ml of cyclohexanol and 2.5 ml of 85% phosphoric acid in a 50

ml round bottom flask.

2. Equip the flask for fractional distillation but don’t pack the column with glass
beads. Apply gentle stirring and heat using the hotplate stirrer and aluminum
jacket.

3. Collect the product in a 25 mL receiving flask that is placed in an ice bath. The
product, cyclohexene, should co-distill over with water mainly at 70-75, but one
can collect up to 85o. If co-distillation is sluggish remove thermometer and
adaptor momentarily and add a disposable pipet of water directly to top of column

4. Carefully separate layers & dry the upper organic layer with anhydrous sodium
sulfate. Decant into a tared vial and determine weight and yield. Use as is for IR
and unsaturation tests; no need for the second distillation

5. Clean-up: after the boiling flask has cooled somewhat, add about 25- 30 ml of
cold water, then solid sodium carbonate in small portions (caution foaming will
occur) until neutralized (foaming stops). Then pour this down the cup sink in
your fume hood with water running.