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5.0 ml of 2-methylcyclohexanol was placed in a 50 ml round bottom flask. Phosphoric acid (85%,...

5.0 ml of 2-methylcyclohexanol was placed in a 50 ml round bottom flask. Phosphoric acid (85%, 5 ml) was added cautiously, and the mixture swirled. Boiling stones were added to prevent bumping during heating. The mixture was heated to reflux temperature and refluxed for 15 minutes. The products were collected between 85-90 ˚C, in a small round bottom flask, cooled in ice water.

Isolation Procedure

The distillate was washed with 2 x 5 ml saturated sodium chloride solution in a 125-ml separatory funnel. The organic layer was transferred to a 50 ml Erlenmeyer flask of known mass (40.12 g).

After collecting the product, you weighed the Erlenmeyer flask to find the combined mass (flask + product mixture) to be 43.54 g.

What is the function of phosphoric acid?

Why would you expect the products to have a lower boiling point that the reactants?

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