Lab 2
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Lab 2

Course: CHEM 232, Spring 2008

School: University of Victoria

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1 Scott Wise February 3, 2007 Lab 2: Preparation and Reactions of Alkenes Objective: To prepare alkenes from the dehydration reaction of -Terpineol and to test the presence of alkenes by Bromine test and Baeyer test. Reactions: Procedure: Refer to Pages 34-35 of Chemistry 232 Laboratory Manual1 Figure 1: Procedure and Observations: Procedure 5 g of -Terpineol was added to 5 mL of 85% phosphoric acid which was...

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Wise 1 Scott February 3, 2007 Lab 2: Preparation and Reactions of Alkenes Objective: To prepare alkenes from the dehydration reaction of -Terpineol and to test the presence of alkenes by Bromine test and Baeyer test. Reactions: Procedure: Refer to Pages 34-35 of Chemistry 232 Laboratory Manual1 Figure 1: Procedure and Observations: Procedure 5 g of -Terpineol was added to 5 mL of 85% phosphoric acid which was distilled along with boiling chips. Observations During the distillation process, the mixture in the round bottom flask was erupting violently, and it popped through the condenser and into the collecting graduated cylinder. 2 Physical Properties: Figure 2: Reagents of Dehydration of -Terpineol Compound -Terpineol MW (g / mole) 154.25 Used 5g Mole 0.03 Physical and Safety Data Mp: -20 C, bp 219 C May cause eye, skin, and respiratory tract irritation. May cause central nervous system depression. Bp: 158, mp: 21 d: 0.97g/mL Corrosive - causes burns. Harmful if swallowed and in contact with skin. May be harmful through inhalation. Very destructive of mucous membranes, respiratory tract, eyes and skin. Mp: 2600, No hazardous reactivity. 85% phosphoric acid 98.0 5 mL 0.05 Carborundum boiling chips N/A 6 chips N/A Figure 3: Products of Dehydration of -Terpineol Compound Mixture of Limonene, Terpinoline, -Terpinene, -Terpinene MW (g / mole) 136.2 Isolated 2.34 g Mole 0.0172 Yield 57% Physical Data Mp: 72.5 C, density: 1.43 g/mL. bp 232 C Experimental Data: Figure 4: Gas Chromatography Analysis Compound Limonene Mixture of Limonene, Terpinoline, -Terpinene, -Terpinene Retention Time 3.28 minutes 2.92 minutes Area 7.38 cm2 26.5 cm2 % composition 100% Compound 28% 3 -Terpineol Alkene Product Blank Cyclohexane Limonene Isoprene Phenylacetylene Toluene Bromine Test Positive Positive Negative Negative Positive Positive Positive Negative Baeyer Test Positive Positive Negative Negative Positive Positive Positive Negative Analysis: During the distillation of -Terpineol and phosphoric acid, the bubbles coming out of the round bottom flask popped and surged into the condenser part of the distillation apparatus. This filled the collecting graduated cylinder with impure alkene product. This affected the percent yield of -Terpineol. The reaction between phosphoric acid and Terpineol is constantly in equilibrium, so it would impossible to completely extract 100% of the alkene product. To get as close to this complete extraction, you would need to continuously distil the products. The percent yield at 57% would be lower if the pop had not happened. According to the Gas chromatography, limonene is present in the mixture of product alkenes at 28%. This is approximately the percentage of limonene if the products were in equal amounts. Conclusion: 4 The alkene product that was produced from the dehydration of -Terpineol, tested positive in the Baeyer Test as well as the Bromine Test. Its percent composition of Limonene was 28%. Questions: 3-Methylcyclohexene and 2-Methylcyclohexene would be produced from the dehydration of reaction of 2-Methylcyclohexanol instead of -Terpineol. The major product would be 2-Methylcyclohexene because the double bond is more highly substituted than in 3Methylcyclohexene. Calculations: 1 Reference: University of Victoria, Chemistry 232 Laboratory Manual, Experiment 1, pages 34-35

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