1. General

a. Make sure that you get all the assigned texts and that you reaad them as well asap. If you have questions, please consult your TA or instructor.

b. You should start writing the introduction for your formal report. It could not hurt either to write up the experimental and the discussion part as you go along with the project. There are no post-labs due for this project since the report replaces those.

c. Review the following subjects: Resolution, Optical purity, Polarimetry,

2. Experimental (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, hence you will need to recrystallize the crude product.

c. The crude product has to be recrystallize from hot water (~1 g dry material/10 mL water). Since your crude product is not completely dry, a ratio of ~1:5 might be a better starting point.

d. It is crucial that the final product is isolated you leave for the day. Why?

e. The final product should be white or off-white after the recrystallization.

3. Experimental (Oxidation of benzylic alcohol with Ce(OH)₃(OOH))

a. It is very important the the Ce(OH)₃(OOH) is reasonably dry for this reaction. The dry product is orange in color and not yellow!

b. It is important to keep the temperature of the reaction mixture between 50-60 ^oC (monitor the temperature using a thermometer). A water bath might be the best heat source here. Too low of a temperature slows down the reaction too much. A significantly higher temperature causes the Ce(OH)₃(OOH) to decompose without oxidizing the alcohol.

c. Make sure that you collect the solid product (Ce(OH)₃) in a separate container for recycling. If you dump anything else in there, you will be the one that is going to recycle the Ceric salt!

d. Since the reaction will require almost the entire lab period, it is highly advisable to get started with it right away. It might be a good idea to monitor the reaction using TLC.

3. Things to think about

a. How can you isolate the (S, S)-form of the diamine?

b. What is the maximum yield (in % and grams) for the tartrate salt assuming that you use the commercially available mixture described in the reader?

c. Suggest a different way to separate the different enantiomeric forms in preparative scale.

d. Why do you have to do the resolution step?

e. Which solvent would be suitable for TLC for monitoring the oxidation reaction?