4-Methylcyclohexene
Lab 22: 4-Methylcyclohexene
Abstract: We treated 4-methylcyclohexanol with phosphoric acid, and after purification we produced the end product 4-methylcyclohexene. We determined we had a pure product based on the results of the tests with Br2 and KMnO4, as well as the IR absorbtion spectrum of the final product.
Purpose:
The purpose of this experiment is to obtain pure 4-methylcyclohexene by reacting 4-methylcyclohexanol and phosphoric acid. Through distillation, extraction, and drying, the crude product is isolated. The crude product is then distilled and collected to produce a product which was determined to be pure after testing it with Br2 and KMnO4 as well as completing an IR spectrum.
Reactions:
1. Main Reaction
2. Competing side reactions:
Separation Scheme:
Procedure: The experiment followed the experimental procedure given by E. Kluger in Introduction to Organic Lab Techniques pages 39-41
(Reference at end)
Calculations
Limiting Reagent Calculations:
Theoretical Yield:
Actual Yield:
Percent Yield:
Observed Properties and Analytical Data:
After the final distillation on the product was complete, it was tested for purity. A few drops of the product were combined with a few drops of Br2/CCl4 to test for unsaturation. The mixture turned colorless, a positive sign for the presence of a double bond that 4-methylcyclohexene contains. The second test mixed a few drops of the product with KMnO4 to test for the presence of alcohol. The color changed to brown, indicating the presence of the desired product. A drop of the product was also tested with IR spectroscopy. There were peaks at both 1600cm-1 and 3300cm-1 which are indicative of an alkene. 1600cm-1 correlates with the C=C stretch, while the 3300cm-1 signal correlates
Abstract: We treated 4-methylcyclohexanol with phosphoric acid, and after purification we produced the end product 4-methylcyclohexene. We determined we had a pure product based on the results of the tests with Br2 and KMnO4, as well as the IR absorbtion spectrum of the final product.
Purpose:
The purpose of this experiment is to obtain pure 4-methylcyclohexene by reacting 4-methylcyclohexanol and phosphoric acid. Through distillation, extraction, and drying, the crude product is isolated. The crude product is then distilled and collected to produce a product which was determined to be pure after testing it with Br2 and KMnO4 as well as completing an IR spectrum.
Reactions:
1. Main Reaction
2. Competing side reactions:
Separation Scheme:
Procedure: The experiment followed the experimental procedure given by E. Kluger in Introduction to Organic Lab Techniques pages 39-41
(Reference at end)
Calculations
Limiting Reagent Calculations:
Theoretical Yield:
Actual Yield:
Percent Yield:
Observed Properties and Analytical Data:
After the final distillation on the product was complete, it was tested for purity. A few drops of the product were combined with a few drops of Br2/CCl4 to test for unsaturation. The mixture turned colorless, a positive sign for the presence of a double bond that 4-methylcyclohexene contains. The second test mixed a few drops of the product with KMnO4 to test for the presence of alcohol. The color changed to brown, indicating the presence of the desired product. A drop of the product was also tested with IR spectroscopy. There were peaks at both 1600cm-1 and 3300cm-1 which are indicative of an alkene. 1600cm-1 correlates with the C=C stretch, while the 3300cm-1 signal correlates
References: Kluger, E. Introduction to Organic Laboratory Techniques: CHM 2211L Course Pack, Spring 2014. XanEdu Publishing, Inc.: Ann Arbor, MI, USA, 2014. p. 39- 41