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Meeting 15 (Acetyl Ferrocene)
Important Announcements:
1. The proposal is due on November 22, 2006 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 November 20, 2006 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 November 21/22, 2006)
1. Referring to the synthesis of ferrocene, answer the following questions.
a. Even though cyclopentadiene is a hydrocarbon, it is relatively acidic. Rationalize this observation.
b. Dimethylsulfoxide used as a solvent in this reaction. Rationalize this choice.
c. Ferrocene can be sublimed in vacuo, sodium cyclopentadienide cannot. 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 acylium ion is considered a weak electrophile. However, a certain part of the crude is a diacylation product. Rationalize this observation.
c. Why is it important to start with a low polarity solvent when performing column chromatography step in this experiment?
d. How many signal do you expect to see for acetyl ferrocene in the 13C-NMR spectrum?