The first quiz will be on April 13, 2004 at 8 am in the lecture. Please make sure that you arrive on time.

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.

Note: The C&EN, March 22, 2004, pp. 51 has an article entitled "Birth of a Drug" which briefly discusses the process of getting approval for a new drug and some other issues.

1. L-(-)-adrenaline is used as a cardiac stimulant. It was isolated from adrenal medulla (name (lat.): adrenes) by two independent groups (Takamine, Aldrich and von Fürth) in 1900 and 1901. It was the first hormone which could be crystallized. The structure determination by Jowett and the first total chemical synthesis by Stolz were achieved in 1904. .

A student obtains a racemic mixture of the compound as a white powder from a sequence of reactions.

a. The student has 6.2 g of the racemic mixture. Suggest a method how he could isolate the desired L-(-) enantiomer.

b. The student obtains 2.2 g of the L-(-)-adrenaline. Calculate the yield.

c. For the isolated enantiomer, he observes an optical rotation of a= - 4.0^o for a solution (400 mg in 10 mL) in a 20 cm cell. What can he conclude about the purity of his sample?

d. Suggest two other methods that he could use to obtain information about the optical purity of his sample?

2. Referring to the oxidation reaction (step 3b), answer the following questions.

a. Why does the temperature has to be carefully controlled in this reaction?

b. What is the melting point of the aldehyde (6) and the benzylic alcohol (5)?

c. What are the most important changes in the IR spectrum of the aldehyde?

d. How can you increase the rate of reaction for this reaction?