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Meeting 15 (Acetyl Ferrocene)
Important Announcements:
1. The proposal is due on November 13, 2009 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 10 pm on November 16, 2009 only one per group! Make sure that you have an electronic copy of your proposal with you (Course ID: 2770701, Password: Chem30CL).
2. The next quiz (=quiz 7) will be administered on November 17, 2009 at 11 am. It will cover ferrocene, acylation of ferrocene and organometallics. Make sure that you show up on time, which means that you have to be seated by 10:55 am. 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. The aclation lab will be on November 12, November 13, November 17 and November 18, 2009.
4. The in-lab work on the research project will be on November 19, November 20, November 24 and November 25, 2009. All work has to be completed by November 25, 2009 at 5 pm. This also includes the submission of the NMR samples.
Homework assignments (due November 12/13, 2009)
1. Referring to the synthesis of acetyl ferrocene, answer the following questions.
a. Identify the electrophile and the nucleophile in this reaction. How is the electrophile generated in the lab? Show pertinent chemical equation(s).
b. Which advantage does the method in a. have?
c. After the reaction is completed, the reaction mixture is poured into a solution of sodium acetate. Explain why. What should the student observe at this point?
d. Why is it important to "neutralize" the organic layer before performing the column chromatography step? Which pH-value is the student looking for here?
e. The crude product has to be purified by flash chromatography. What is used as stationary phase? What is the mobile phase? Which compounds are mainly separated here?
f. In many cases, the student observes a dark blue or dark green color at some point during the work-up. Rationalize this observation.
g. The 13C-NMR spectrum of acetyl ferrocene exhibits four signals at from d = 69-80 ppm. Rationalize this observation.
h. Ferrocene itself only exhibits one signal in the 1H-NMR and the 13C-NMR spectrum. Explain.