ATTN: answers to the below questions are due at the start of your second lab period; these answers should be part of your pre-lab write-up.

1. Referring to the resolution of 1,2-diaminocyclohexane (step 1), answer the following questions.

a. Which isomer of tartaric acid used in this step? Why?

b. Why is glacial acetic acid added in this reaction?

c. Assuming you isolated 8.5 g of the crude product, which is still not entirely dry, how much water should be used to recrystallize the crude?

d. What is the theoretical yield (in g based in the quantities given in the reader) for the diammonium salt that you are planning to isolate? Show calculations.

e. How can the success of the resolution step be assessed?

2. Referring to the oxidation of the benzylic alcohol (step 3), answer the following questions:

a. What is the function of the dimethylsulfoxide in this reaction?

b. The temperature of the reaction has to be carefully controlled. Explain briefly.

c. The crude product is recrystallized from hot methanol. Rationalize this choice. Which precautions should be taken here?

d When monitoring the reaction using TLC, which of the compounds in the reaction mixture (benzylic alcohol, aldehyde and phenol) do you expect to have the highest R_f-value? Rationalize this observation.

3. How does "kinetic resolution" work?