last updated Thursday, February 22, 2007

Meeting 15 (Acetyl Ferrocene)

Important Announcements:

1. The proposal is due on March 2, 2007 at 5 pm in YH 3077E (If you have problems please see me asap!). The proposal has to be submitted to turnitin.com as well (same course ID as before).

2. The next quiz will be administered on March 1, 2007 at 12 pm. It will cover the ferrocene, the acylation reaction and the formation of heterocycles.

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.

Homework assignments (due February 26/27, 2007)

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

a. How is cyclopentadiene obtained in the lab? Provide a balanced chemical equation and classify the reaction.

b. Compared to cyclopentane and cyclopentene, cyclopentadiene is much more acidic. Rationalize this observation.

c. Potassium cyclopentadienide dissolved well in DMSO, while ferrocene does not. Explain.

2. 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 reaction affords a mixture of mono and diacylation product. Show the structure of this compound and rationalize this observation.

c. Why is it important to start with a low polarity solvent when performing column chromatography step in this experiment?

d. Sketch a ¹H-NMR spectrum for acetyl ferrocene and label the peaks.