last updated Friday, February 12, 2016

Meeting 14 (Acetyl Ferrocene)

Important Announcements:

1. Administrative Issues

a. There will be no in-lab meeting on February 25 and February 26, 2016. This will allow you to finish the proposal and/or have an early start on the weekend.

b. There will be no separate prelab for meeting 15 (column chromatofraphy part of the acetyl ferrocene experiment).

2. Ferrocene project

a. The proposal for the ferrocene project is due by Friday, February 26, 2016 by 12:00 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 7 (!) pages and be submitted in a report cover together with the important synthetic and spectroscopy references correctly labeled and organized. Do not forget to include the safety information. The entire folder will be returned starting on Monday, February 29, 2016. The proposal has to be submitted to turnitin.com as well (same course ID as before) by Friday, February 26, 2016 at 12:00 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 2, 2016 and will extend through Friday, March 6, 2016 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 18 and February 19, 2016  (synthesis and isolation of the crude), February 23 and February 24, 2016  (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.

3. Quizzes

a. Quiz 6 will be administered on February 16, 2016 at 9 am. It will cover the Suzuki reaction and the esterification.

b. Quiz 7 will be administered on February 23, 2016 at 9 am.  It will cover nitration, acylation and final project.

Homework assignments (due February 18 and February 19, 2016)

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

a. What is the electrophile in this reaction?

b. What is used as the catalyst in the reaction? Rationalize the choice.

c. Name three pieces of evidence that establishes the C-O bond order in the electrophile. Provide details.

d. Upon completion, the reaction mixture is poured into water. Which purpose does this serve?

e. The mixture obtained in d. is extracted with ethyl acetate. The combined organic layer are extracted with saturated sodium bicarbonate solution. Which purpose does this serve?

f. The student acquires a TLC for the crude product (silica, petroleum ether:ethyl acetate (9:1)). Sketch the plate showing the crude in lane 1, acetyl ferrocene in lane 2 and ferrocene in lane 3.

g. How many signals does the ¹³C-NMR spectrum of diacetylferrocene formed as byproduct exhibit? Indicate the chemical shift and rationalize their locations.

h. Which range does the student have to measure when acquiring the infrared spectrum of the product? Rationalize the choice.