last updated Tuesday, February 17, 2015

Meeting 14 (Acetyl Ferrocene)

Important Announcements:

1. Ferrocene project

a. The proposal for the ferrocene project is due by Friday, February 20, 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, February 23, 2015. The proposal has to be submitted to turnitin.com as well (same course ID as before) by Friday, February 20, 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 Tuesday, March 3, 2015 and will extend through Friday, March 6, 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 February 24 and 25 (synthesis and isolation of the crude), February 26 and 27, 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 February 24, 2015 at 9 am. It will cover nitration, acylation and heterocyclic chemistry.

Homework assignments (due February 24 and February 25, 2015)

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. Why is this electrophile considered a weak electrophile?

c. How can infrared spectroscopy can be used to establish the C-O bond order? Be specific.

d. What is the proper temperature for the reaction? How is this temperature established in the lab?

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 crude product is purified using column chromatography. What is used as mobile phase here? In which sequence do the compounds elute from the column? Rationalize the sequence.

g. How many signals does the ¹³C-NMR spectrum of acetyl ferrocene exhibit? Indicate the chemical shift and rationalize their locations.

h. Which range should the student measure when acquiring the infrared spectrum of the product?