General

By now, you should have performed some literature search already which should enable you to write an introduction for your formal research paper. The draft of the paper will be due on January 29, 2004 at 5 pm in YH1217. (A detailed list what to include into the draft will be posted on one of the next pages)

Experimental

1. Step 3 b (Oxidation of the alcohol with Ce(OH)₃(OOH))

a. Preparation

The Ce(OH)₃(OOH) should be as dry as possible before using it in the reaction. It also couldn't hurt to use it as a powder without any bigger lumps. Why? The dry product is ornage-brown and not yellow.

b. Running the Reaction

It is important to keep the temperature of the reaction mixture between 60-70 ^oC (monitor the temperature using a thermometer). A water bath might be the best heat source here since it is easy to control. Too low of a temperature slows down the reaction too much. A significantly higher temperature causes the Ce(OH)₃(OOH) to decompose too quickly without oxidizing the alcohol. Monitor the reaction using TLC.

c. Workup

Make sure that you collect the solid product (Ce(OH)₃) in a separate container (provided by the TA) for recycling. You should perform the actual oxidation reaction this week, and initiate the crystallization.

2. Resolution of the diamine

a. It is important that the diamine is added slowly. Why?

b.The desired product crystallizes together with some trapped material.

c. The crude product has to be recrystallize from hot water (~1 g of solid/5 mL water), since the crude product is not completely dry. The solubility curve is relatively steep close to the boiling point of water. So, make sure that you bring the solution to a boil.

d. It is crucial that the final product is isolated you leave for the day. You cannot store the solution for crystallization. Why?

e. The final product should be white or off-white after the recrystallization and be stored in a closed container.