last updated Sunday, February 16, 2014

Meeting 14 (Acetyl Ferrocene)

Important Announcements:

1. Ferrocene project

a. The proposal for the ferrocene project is due by Friday, February 28, 2014 by 4:30 pm in YH 3077 E (If you have problems please see the instructor asap!). Late proposal will not be accepted and will result in an automatic "F"-grade for the course. 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 18, 2013. The proposal has to be submitted to turnitin.com as well (same course ID as before) by Friday, February 28, 2014 at 10:00 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 4, 2014 and will extend through Friday, March 7, 2014 at 5 pm. All NMR samples have to be submitted by then. There will be no chance to complete the characterization during week 9 or 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 20 and 21 (synthesis and isolation of the crude), February 25 and 26, 2014 (column chromatography). The postlab for the acylation reaction is due together with your notebook at the final exam.

d. Many groups have not picked up their project as of now. 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))

2. Administrative Issues

a. There will be no additional prelab for meeting 15.

b. There will be no lab on February 27, 2014 and February 28, 2014 to provide ample time for the students to work on the presentation. \

c. The instructur will also offer a demo on the GC/MS (1-2 pm) and the HPLC (3-4 pm) on February 27, 2014 for those that are interested (minimum attendance is 7 students).

3. Quizzes

a. Quiz 6 will be administered on February 18, 2014 at 9 am. It will cover the Grignard reaction, the esterification and the drug design. Make sure that you show up on time, which means that you have to be seated by 8:55 am. Otherwise you will not be allowed to take the quiz. Students that provided responses that are exceeding word limit will receive a significant point deduction. The quizzes have asked for short and concise answers and not for random information in form of an essay.

b. Quiz 7 will be administered on February 25, 2014 at 9 am. It will cover nitration, acylation and heterocycle chemistry. Make sure that you show up on time, which means that you have to be seated by 8:55 am. Otherwise you will not be allowed to take the quiz. Students that provided responses that are exceeding word limit will receive a significant point deduction. The quizzes have asked for short and concise answers and not for random information in form of an essay.

Homework assignments (due February and November 13, 2013)

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

a. What is the electrophile in this reaction? How is it obtained in the Chem 30CL lab?

b. Provide the structure of the electrophile. Provide three pieces of evidence that the C-O bond order is very high in the electrophile.

c. What is the proper temperature for the reaction? Why is it important to maintain this temperature?

d. 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?

e. 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?

f. How many signals does the ¹³C-NMR spectrum of acetyl ferrocene exhibit? Rationalize their locations.

g. Why is the melting point of acetylferrocene lower than the one of ferrocene?