last updated Thursday, May 15, 2008

Meeting 15 (Acetyl Ferrocene)

Important Announcements:

1. The proposal is due on May 23, 2008 at 5 pm in YH 3077 E (If you have problems please see me asap!). Late proposal will not be accepted and will lead to an automatic "F"-grade for the course. The important references have to be attached to the proposal. The proposal has to be submitted to turnitin.com as well (same course ID as before) by 11 pm on May 23, 2008, only one per group! Make sure that you have an electronic copy of your proposal with you.

2. The last quiz (=quiz 7) will be administered on May 22, 2008 at 12 pm. It will cover the nitration reaction and the acylation reaction. Make sure that you show up on time. Otherwise you will not be allowed to take the quiz.

3. In the lab, you will only carry out the acylation of ferrocene, but not the synthesis of ferrocene. This part will be done individually and not in groups.

Homework assignments (due May 20/21, 2008)

1. Referring to the synthesis of acetyl ferrocene, answer the following questions.

a. How is the acylium ion generated in the lab? Show pertinent chemical equation(s).

b. The acylium ion is considered a weak electrophile compared to the nitronium ion. Which advantage(s) does this have?

c. Why is it important to "neutralize" the organic layer before performing the column chromatography step? Which pH-value is the student looking for here?

d. How is the crude product applied to the column?

e. During the flash chromatography step different solvents are used. Which ones are those and why are they used?

f. In which sequence do the compounds elute off the column?

g. The ¹H-NMR spectrum of acetyl ferrocene exhibits four signals at from d = 65-85 ppm. Rationalize this observation.

h. A student reacts acetyl ferrocene with hydroxylamine and a base. Which products are formed?