A common method for synthesizing alkenes is by dehydrating (removing the element

Question

A common method for synthesizing alkenes is by dehydrating (removing the elements of water) an alcohol. The dehydration is accomplished by heating the alcohol with either phosphoric or sulfuric acid. In this experiment, the dehydration reaction is illustrated by the conversion of 2-methylcyclohexanol to a mixture of alkenes (remember the Saytzeff rule).

Each step of this E1 elimination reaction is reversible and thus, the reaction may be driven to completion by removing one or more of the products, in this case, the alkenes. For this reason, the reaction can be done using the setup for a simple distillation.

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 %u02DAC, in a small round bottom flask, cooled in ice water.

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).

Explanation / Answer

43.54 - 40.12 = 3.42

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