1. General

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

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 ~1:3-1:5 might be a better starting point, since it is easier to add water than removing it.

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 DMSO/HBr)

a. It is important to keep the temperature of the reaction mixture around 105-110 ^oC (monitor the temperature using a thermometer). If the temperature was too low or too high, the reaction will slow down. A significantly higher temperature causes the HBr to boil off.

b. Since the reaction will require two hours, it is highly advisable to get started with it right away. It might be also a good idea to monitor the reaction using TLC. Which solvent should be used?

c. Warm methanol (~ 50 ^oC) is used to recrystallize the crude aldehyde. Why?

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.