ATTN: answers to the below questions are due at the start of your second meeting (4/2 or 4/3); these answers should be part of your pre-lab write-up. The first quiz will be administered in lecture on Tuesday, April 7, 2009 at 12 pm (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 12 pm right after the morning lab! 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. This rule will apply for all quizzes administered this quarter!

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

a. Why is methanol used as solvent for the reaction?

b. Why is it so difficult to dissolve sodium hydroxide pellets in methanol?

c. Why is it important to chill the solution prior addition of the formaldehyde solution? How many equivalents of formaldehyde are added?

d. A student allows 24 hours for the reaction to occur and then observes a dark-green mixture which separates upon standing. What happened here? How should he proceed?

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

f. A student did not read the procedure carefully enough and extracts the resulting mixture from e. with hexane. What would he observe?

g. How is the organic layer dried?

h. How is the solvent removed to obtain the crude product?

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

j. The crude product is recrystallized from hexane. Rationalize this choice. Why is the solution not placed in an ice-bath like usual?