5.0 ml of 2-methylcyclohexanol was placed in a 50 ml round bottom flask. Phospho

Question

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.

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.

The mass of the product mixture isolated from the reaction is 3.420 (g)

Major product is 1-methylcyclohexene

Minor product is 3-methylcyclohexene

Molecular weight of the products is 96.17g/mol

A) What is the theoretical mass yield, considering that you started with 5.0 ml of 2-methylcyclohexanol (g)?

B) Determine %yield

**SHOW WORK PLEASE**

Explanation / Answer

A) 1 molecule of 2-methylcyclohexanol would yields 1 molecule of methylcyclohexene (both isomers together)

moles of 2-methylcyclohexanol = (5 ml x 0.93 g/ml)/114.2 g/mol = 0.041 mol

Theoretical mass of product formed = 0.041 mol x 112.17 g/mol = 4.60 g (100% yield)

B) % yield = 3.420 g x 100/4.60 g = 74.35 %

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