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Meeting 14 (Acetyl Ferrocene)
Important Announcements:
1. Ferrocene project
a. The proposal for the ferrocene project is due by Friday, November 21, 2014 by 4:30 pm in YH 3077 E (If you have problems please see the instructor asap!). Late proposal will not be accepted. The proposal should not be longer than 6 (!) pages and be submitted in a report cover together with the important synthetic and spectroscopy references. The entire folder will be returned starting on Monday, November 24, 2014. The proposal has to be submitted to turnitin.com as well (same course ID as before) by Friday, November 21, 2014 at 5:00 pm (only one per group)! Make sure to include the email address of both students on the front cover.
b. The research project starts on Tuesday, December 2, 2014 and will extend through Friday, December 5, 2014 at 5 pm. All NMR samples have to be submitted by then. There will be no chance to complete the characterization during week 10. Generally, students will only be allowed to attend their own sections, which means that the work has to be coordinated between the students in the group. Any exceptions have to be approved by the instructor.
c. 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 acylation lab will be on November 20 and 21 (synthesis and isolation of the crude), November 25 and 26, 2014 (column chromatography). The postlab for the acylation reaction is due together with your notebook at the final exam.
d. Several students have not picked up their project at this point. Note that you will have to show up in person to do so. The project will not be emailed to you.
e. "Fc" in the project stands for ferrocenyl (=Fe(C5H5)(C5H4))
f. There will be no additional prelab for meeting 15.
2. Quiz 7
Quiz 7 will be administered on November 20, 2014 at 11 am. It will cover nitration, acylation and heterocyclic chemistry.
Homework assignments (due November 20 and November 21, 2014)
1. Referring to the synthesis of acetyl ferrocene, answer the following questions.
a. What is the electrophile in this reaction? Provide the structure of the electrophile.
b. How is it obtained in the Chem 30CL lab?
c. The carbonyl carbon in the electrophile displays a very unusal chemical shift in the 13C-NMR spectrum. Where does the signal appear? Rationalize this observation.
d. What is the proper temperature for the reaction? Why is it important to maintain this temperature?
e. After the reaction is completed, the reaction mixture has to be "neutralized". How is this task accomplished in the lab? What is the student looking for here?
f. The crude product is purified using column chromatography. What is used as mobile phase here? In which sequence do the compounds elute from the column?
g. Why is the column not pretreated with a 1% triethylamine solution?
h. How many signals does the 1H-NMR spectrum of acetyl ferrocene exhibit? Indicate the multiplet structure, the chemical shift and the integration. Rationalize their locations.