last updated Thursday, October 14, 2004

Problems Set #6


ATTN: answers to the below questions are due at the start of your lab period of Meeting 6; these answers should be part of your pre-lab write-up.


The draft version of paper is due on 10-29-2004 at 5 pm in YH 1217. The draft version is worth 15 points, the final paper 45 points. For more information what the draft is supposed to contain see here. Late submission will receive less credit. The more of your work you submit here, the more feedback you will get, which will beneficial for the final version. We will try to return the reports by Monday.

The third quiz will be on October 21, 2004 in lecture. Please make sure that you arrive on time.


1. Referring to the epoxidation reaction,

a. which purpose does this TLC serve in this reaction?

b. what happens if the pH-value drops below 9.5 in the reaction?

c. a student has about half of the catalyst that he is supposed to have. Can he carry out the epoxidation reaction? If yes, what would change for him?

2. A student plans to use 0.5 g of 4-methylstyrene for his epoxidation. His procedure requires the use of 7 mole% of the Jacobsen catalyst and 1.2 equivalents of oxidant (bleach).

a. How many grams of the catalyst are needed?

b. What is the volume of bleach required in this experiment?

3. How do substituents on the phenyl ring of a cinnamic ester influence the cis/trans ratio?

4. Why are chiral epoxide good tools for organic synthesis?