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Experiment 1: Mechanism of Nitrile Oxide and Alkene Cycloaddition

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Experiment 1: Mechanism of Nitrile Oxide and Alkene Cycloaddition
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: 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. 4. Balanced Equations:
Sytrene + Benzaldehyde Oxime OR
OR

Cis-Stilbene + Benzaldehyde Oxime OR
OR

Trans-Stilbene + Benzaldehyde Oxime
OR
OR

5. Reagents and Quantities: Reactant | MW (g/mol) | Grams | Moles | Molarity | Density (g/mL) | Volume (mL) | Cis-Stilbene | 180.25 | 0.6 | 0.6/180.25 = 0.003 | 0.33 M | 1.011 | 9.1 | Trans-Stilbene | 180.25 | 0.3 | 0.3/180.25=0.002 | 0.33 M | 0.9707 | 5.2 | Styrene | 104.15 | 0.227 | 0.227/104.15 = 0.002 | 0.33 M | 0.909 | 6.6 | 5.25 wt% NaOCl | 74.44 | Trans-S Rx: | | --- | 1.06 | Trans-S Rx: 6.0 / 2 min | | | Cis-S Rx: | | | | Cis-S Rx:12.0 /4 min | | | Styrene Rx: | | | | Styrene Rx:5.0 | CH2Cl2 | 84.93 | | | --- | 1.33 | | 2.3 M Benzaldehyde Oxime | 121.13 | Trans-S Rx: | 0.001 L x 2.3 mol/L = 0.0023 | 2.3 M | ---- | Trans-S Rx:1.0 | | | Cis-S Rx: | 0.002 L x 2.3 mol/L = 0.0046 | | | Cis-S Rx:2.0 | | | Styrene Rx: | 0.001 L x 2.3 mol/L = 0.0023 | | | Styrene Rx:1.0 / 4 min |
Pre-Lab 1
Set Up: 2:00 – 2:10
Clean Up: 4:45 – 5:00
In an Erlenmyer Flask, a solution of methylene chloride
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