CHEM
Epoxidation of Cyclohexene.pdf

Obtain the weight of your product the ft ir spectrum

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and remove the dichloromethane with a rotary evaporator. Obtain the weight of your product, the FT-IR spectrum, and the 1 H NMR spectrum. If you product looks clean, save it for next week’s dihydroxylation experiment. Don’t worry, we will provide 1,2-epoxycyclohexane if your synthesis was not completely successful. Place the remainder of your chemical waste for this experiment in a container for halogenated waste. Halogenated Waste Plastic Waste Glass Waste cyclohexene dichloromethane meta -chlorobenzoic acid meta -chloroperbenzoic acid sodium carbonate sodium chloride water Gloves Plastic Pipettes Weigh boats Glass Pipettes Analysis Questions 1. Draw the mechanism for the epoxidation of cyclohexene. a. Which oxygen from the peroxy acid is being added to the cyclohexene? b. Is the cyclohexene being oxidized or reduced? Explain.
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331L EPOXIDATION c. What happens to the two hydrogens that are attached to the carbons involved in the double bond in the starting alkene? (i.e. what stereochemistry do you end up with?) How does the mechanism explain this? 2. How is 1,2 cyclohexane epoxide separated from the m -CPBA and the m -CBA byproduct? Where are the latter two chemicals found, and why? 3. Calculate your percent yield. Show your work for full credit. 4. Include a PDF of the IR spectrum of your product. Label all major peaks with corresponding functional groups. 5. Include a PDF of the proton NMR spectrum of your product. (Integrate and peak pick, as usual.) Identify which product hydrogen(s) each peak corresponds to. 6. Where you successful in your synthesis? Use your spectra to justify your answer. Be specific.
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  • Spring '13
  • KINGSTON
  • pAA

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