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Synthesis and Characterization of Ferrocene, Acetylferrocene and Ferrocenylethanol
Submitted by John Henry Acquaye, Department of Chemistry, University of Redlands (/user/franciskojo1618) on July 16, 2012 -­ 10:57am
Categories
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(/taxonomy/term/38)
Topics Covered: Synthesis and reactivity (/taxonomy/term/35)
Course Level: Upper Division (/taxonomy/term/14)
Subdiscipline: Organometallic Chemistry (/taxonomy/term/10)
Corequisites: Organic Chemistry
Prerequisites: General Chemistry
Description: This project is designed to develop the research skills that are required to tackle projects that are larger and more complex than those encountered in first and second
year chemistry courses. The lab is an integrated project-­oriented laboratory including synthesis and the use of instrumental techniques such as UV-­Visible and
infrared, 1H-­NMR and 13C-­NMR spectrometry, chromatography (HPLC, TLC) and cyclic voltammetry. Attention also will be paid to developing general laboratory skills
such as lab safety, literature searching, experiment design, working with laboratory instruments, keeping a laboratory notebook and oral presentation Usually students will work together in groups. Each student (or group) will undertake three or four projects, of 3-­4 weeks duration, chosen in consultation with the
laboratory instructors. At the beginning of each project students will meet together with the laboratory instructors to generate a detailed plan for laboratory
work. This phase includes literature searching, study and presentation of the framework of the project, experiment design and optimization (if appropriate),
familiarization with instruments, and detailed planning of the experimental procedures. In addition, students will answer all questions in the procedures when
appropriate. Students are required to write appropriate pre-­lab in their laboratory notebooks for each day's activities.
This is one of five projects that students in Advanced Laboratory perform in the spring semester. Students work in groups of two or three. The project is usually three
weeks long involving two three hour periods in a week.
Learning Goals: Students will be able to carry out more extended synthetic procedures.
Students will learn to use various analytical instrumentation to characterize the complexes.
Students will write at least a six page lab report.
Students will incoporate the experimental data into the report and interpret the data in relation to the structural changes observed in the complexes.
Students will learn to communicate their report in an oral presentation.
Equipment needs: UV-­Visible
IR spectrophotometer
NMR
GC
HPLC
Potentiostat
All reagents are provided.
Implementation Notes: Students are required to consult the given references for the necessary procedures.
Day 1: Cracking of dicyclopentadiene and the synthesis of ferrocene (Reference: Woollins, J. D., editor;; Inorganic Experiments;; VCH publisher, Inc., New York, NY.
1994;;)
Day 2: Determine the melting pt. of ferrocene. Record the IR and the UV-­vis (in ethanol) spectra of ferrocene, 1H NMR (in CDCl3) spectra of ferrocene. Record the
cyclic voltammogram of ferrocene (in CH2Cl2 with tetrabutylammoniun hexaflorophosphate as supporting electrolyte).
Day 3: Synthesis of acetylferrocene from ferrocene (Reference: Woollins, J. D., editor;; Inorganic Experiments;; VCH publisher, Inc., New York, NY. 1994;; p60) Day 4: Determine the melting pt. of acetylferrocene. Record the IR and the UV-­vis (in ethanol), 1H NMR (in CDCl3) spectra of acetylferrocene. Record the cyclic
voltammogram of acetylferrocene (in CH2Cl2 with tetrabutylammoniun hexaflorophosphate as supporting electrolyte).).
Day 5: Reduction of acetylferrocene with LiAlH4 (Reference: Hamilton, D. E.;; J. Chem. Educ. 1991, 68, A143)
Day 6: Record the melting point, IR and the UV-­vis (in ethanol), 1Hnmr (in CDCl3) spectra of ferrocenylethanol. Record the cyclic voltammogram of ferrocenylethanol
(in CH2Cl2 / tetrabutylammoniun hexaflorophosphate as supporting electrolyte).). Resolution of enantiomers by HPLC (Reference: Armstrong, D. W.;; DeMond,
W.;; Czech, B. P.;; Anal. Chem. 1985, 57, 481-­484.)
Time Required: Three weeks of two three hour lab per week
Evaluation
Evaluation Methods: A detailed project report is required at the end. The project report should include the following:
1. Title, date, your name and partner's name.
2. A two page introduction of the project, the complexes made, literature description of the complexes you made or of similar complexes.
3. A list of chemicals that you used and the MSDS information.
4. Synthetic procedures written in your own words. (“See reference” is not acceptable). Have a good written procedure describing exactly what we did.
5. Use CHEM DRAW for all appropriate drawings.
6. Methods of characterization (Instrumentation) and information obtained there from.
7. Discussion: synthesis, characterization and resolution of the enantiomers. At least three pages of discussion with relevant references from the literature to
support your reasoning.
8. Answers to all questions.
9. Conclusion;; at least, a one-­page summary of the project. Also include comments and suggestions for future improvement of the project.
10. List of References
11. A rough draft of the report is required. This is graded with comments and suggestions from the instructors and returned to the students. A final report
is required in a week.
12. In addition, the lab notebooks are collected and graded twice during the semester. There is also a final exam with questions based on experimental
procedures, spectroscopy and the interpretation of data.
13. Oral presentation of the project.
Evaluation Results: Generally, students do very well in this course with grades ranging between B+ and A. Grades distribution for the various components of the course are: 50% for
lab reports, 20% for final exam, 20% for lab notebook and 10% two oral presentations.
The first draft is sometimes poorly written by the majority of the students Students forget to tie in and discuss the significance of the spectroscopy data and also
the cyclic voltammetry. Even though students have taken the spectroscopy course in organic chemistry, they forget to interpret the IR and nmr in relation to the
structural changes observed.
I give the students sufficient comments and suggestions to enable them rewrite the report. Almost all students come to discuss the raugh draft with me before
they write the final report. In general the final report tends out to be of much higher quality.
Rating: Creative Commons License: (http://creativecommons.org/licences/by-­nc-­sa/3.0/)
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Julia Metzker, Georgia College (/user/jkmetzker)
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