List of possible alkenes for epoxidation:

1-Methyl-cyclohexene, Styrene, 1-Methylstyrene, 4-Methylstyrene, 4-Chloro-a-methylstyrene, 1,2-Dihydronaphthalene

Assume a weight of 120 g/mol for your unknown alkene and calculate the amount of catalyst required accordingly. If your TA asks you to add PNO, use the same number of moles like you use for the catalyst. What would change if you have a higher or lower quantity of the catalyst?

Make sure that you close the flask with some parafilm. The hot plate has to be cold. Why?

TLC is used to monitor the reaction and to optimize the solvent used in the column chromatography:

The reaction should be terminated if the alkene is not visible anymore. You might have to spot a little heavier at the end of the reaction in order to detect small quantities of the alkene.

A good solvent (mixture) should show a good separation of the epoxide and the alkene (difference in R_f-values ~0.3). The epoxide should have a R_f-value about 0.4. Why?

The spotting should be performed using a capillary spotter (you will have to make them yourself). After you developed the plate in your TLC chamber, the TLC plate should be dried briefly and then placed under the UV-light to visualize the alkene (Mark the spot with a pencil). Then drip it briefly into the staining solution (Ceric/Molydbenum), wipe the backside clean and then place it on a warm hot plate. The Mo(VI)-compound in the solution reacts with polar compounds (epoxides, aldehydes, ketones) to form a dark blue Mo(V)-complex. A blue spot appears on the plate.

It is very important that your crude product is dried as good as possible. Due to the fact that you will perform the column chromatography the following week, you need to store the crude in a vial. It might be a good idea to place a small quantity of Na₂SO₄ in there.

When you boil off the solvent, keep in mind that your product is a liquid. Therefore you should not boil it off to dryness. Generally, a small quantity of a dark brown oily residue will remain.