last updated Wednesday, November 06, 2013

Meeting 14 (Acetyl Ferrocene)

Important Announcements:

1. Ferrocene project

a. The proposal for the ferrocene project is due by Friday, November 15, 2013 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, November 15, 2013 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, November 19, 2013 and will extend through Friday, November 22, 2013 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 November 12 and 13 (synthesis and isolation of the crude), November 14 and 15, 2013 (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 November 26, 2013 and November 27, 2013 to provide ample time for the students to work on the presentation.

3. Quizzes

a. Quiz 6 will be administered on November 7, 2013 at 12 pm. It will cover the Grignard reaction and the esterification. Make sure that you show up on time, which means that you have to be seated by 11:55 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 November 14, 2013 at 12 pm. 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 11:55 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 November 12 and November 13, 2013)

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

a. What is the electrophile in this reaction?

b. The electrophile is obtained by the reaction of acetic acid anhydride and concentrated phosphoric acid. Which advantages does this approach have?

c. After the reaction is completed, the reaction mixture has to be "neutralized". How is this task accomplished in the lab?

d. Why is it important to dry the combined organic layer throroughly?

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 1H-NMR spectrum of acetyl ferrocene exhibit? Rationalize their locations.

g. Based on the data provided in the lab manual, what would be the proper concentration for the acquisition of the UV-Vis spectrum of acetyl ferrocene?

h. Why did the instructor recommended to measure the range from 450-4000 cm-1 for this compound?