last updated Thursday, February 23, 2006

Meeting 15 (Acetyl Ferrocene)

Important Announcements:

1. The proposal is due on March 2, 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 (CourseID:1415142).

2. The next quiz will be administered on March 7, 2006 at 12 pm. It will cover the entire ferrocene project, organometallics and drying of solvents.

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 Februay 28/March 1)

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

a. Cyclopentadiene is not commercial available. How is it obtained in the lab?

b. Why is cyclopentadiene more acidic than cyclopentane?

c. Why is dimethylsulfoxide used as a solvent in this reaction?

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

a. How is the acylium ion generated in the lab?

b.Why is the acylium ion considered a weak electrophile? Which implication does this observation have?

c. Why is the mixture "neutralized" after the reaction?

d. A student obtains a TLC for his crude product using a mixture of petroleum ether. What would he observe? What would change if uses ethylacetate instead?

e. Why is it not necessary to pretreat the column with triethylamine?

3. Describe the reaction of acetyl ferrocene with

a. 4-nitrobenzaldehyde in basic ethanolic solution

b. hydroxylamine hydrochloride/sodium acetate in ethanol

c. 4-Nitrophenylhydrazine