ATTN: answers to the below questions are due at the start of your second meeting (1/8 or 1/9); these answers should be part of your pre-lab write-up. The first quiz will be administered in lecture on Monday, January 12, 2009 at 8 am (covering step 2, step 3 and the introduction to asymmetric synthesis). It is the student's responsibility to arrive on time even if the lecture is at 8 am. Late arrivals (even if it is only one minute) will not be allowed to take the quiz, which means that you will receive an automatic zero score for the quiz. If you do not place your name on the quiz to assume authorship, you will receive a zero score as well! You cannot add the name after time was called because this is considered cheating.

1. Referring to step 2 (Synthesis of 2,4-Di-tert.-butyl-6-hydroxymethylphenol), answer the following questions.

a. Even though sodium hydroxide dissolves fairly well in methanol (~24 g/100 mL at 20 ^oC ), many students experiencing problems to dissolve the NaOH pellets in the methanolic phenol solution. Rationalize this observation and explain how this problem can be solved.

b. One point that was stressed in lecture is that the Erlenmeyer flask has to be sealed during the 24 hours of stirring. Explain briefly.

c. How should the reaction mixture look like if the reaction went according to plan? How does it look if things went wrong?

d. The reaction mixture is poured into water and the mixture then acidified using concentrated hydrochloric acid. Rationalize this step and provide pertinent chemical equations.

e. The mixture is subsequently extracted using dichloromethane. How much is used for every extraction and how many extractions are performed?

f. Why is it important to minimize the amount of anhydrous sodium sulfate used during the workup?

g. How is the solvent removed here to obtain the crude product?

h. A TLC is acquired for the crude and for the final product. Which information can the student gather from these TLCs?

i. The crude product is recrystallized from hexane. Rationalize this choice.