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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 13, 2015 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 16, 2015. The proposal has to be submitted to turnitin.com as well (same course ID as before) by Friday, November 13, 2015 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 Thursday,November 19, 2015 and will extend through Wednesday, November 25, 2015 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 12 and November 13, 2015 (synthesis and isolation of the crude), November 17 and November 18, 2015 (column chromatography). The postlab for the acylation reaction is due together with your notebook at the final exam.
d. "Fc" in the project stands for ferrocenyl (=Fe(C5H5)(C5H4))
f. There will be no additional pre-lab for meeting 15.
2. Quiz 7
Quiz 7 will be administered on November 12, 2015 at 11 am. It will cover nitration, acylation and final project.
Homework assignments (due November 12 and November 13, 2015)
1. Referring to the synthesis of acetyl ferrocene, answer the following questions.
a. What is the electrophile in this reaction?
b. How is the electrophile in the lab?
c. Name three pieces of evidence that show that the C-O has a bond order close to three. Provide details.
d. What is the solvent in this reaction?
e. After the reaction is completed, the reaction mixture has to be "neutralized". What is the student looking for here? Which observations does the student make during this step?
f. The student acquires a TLC for the crude product (silica, petroleum ether:ethyl acetate (9:1)). Sketch the plate showing ferrocene in lane 1, acetyl ferrocene in lane 2 and the crude in lane 3.
g. How many signals does the 1H-NMR spectrum of diacetylferrocene formed as byproduct exhibit? Indicate the chemical shift and rationalize their locations.
h. Which range should the student measure when acquiring the infrared spectrum of the product? Rationalize the choice.