Experiment 1: Mechanism of Nitrile Oxide and Alkene Cycloaddition

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Experiment 1: Mechanism of Nitrile Oxide and Alkene Cycloaddition 1. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene. 2. Plan: Each student in a group of three will work to create a reaction with the Benzonitrile Oxide with, cis-stilbene, trans-stilbene, or styrene in an Erlenmyer flask. With this Reaction solution thin layer chromatography will be performed using each reaction solution. The different reactions will then be compared by running co-spot TLC’s. An NMR of the crude products from each reaction will be taken. 3. References: * Chemistry 173Q Organic Chemistry Lab:…show more content…
(4:10 – 4:30) Find Rf values and diagram each TLC plate in lab notebook. (4:30 – 4:45) ------------------------------------------------------------------------------------------------------------------------------- Diagram 1: Vacuum Filtration Diagram 3: Thin Layer Chromatography Diagram 2: Rotary Evaporator Maria Mo February 8, 2016 Experiment 1: Mechanism of Nitrile Oxide and Alkene Cycloaddition 6. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene; to purify the crude product of either trans-stilbene, cis-stilbene, or styrene reaction. 7. Plan: Each student in a group of three will work to purify the product of the reaction with cis-stilbene, trans-stilbene, or styrene. The crude products will be purified through recrystallization. This purification process will be performed several times. When the recrystallization is complete, a vacuum filtration will be executed to filter out the crystals. An NMR spectrum will be taken of the recrystallized product. 8. References: * Chemistry 173Q Organic Chemistry Lab: Laboratory Manual Notes * Mohrig, Jerry R., Christina Noring Hammond, and Paul F. Schatz. Techniques in Organic Chemistry. 3rd ed. N.p.: n.p., 2010. Print. Pre-Lab 2 Set Up: 2:00 – 2:10 Clean Up: 4:45 – 5:00 In the round bottom flask containing the recrystallized crude

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