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Department of Chemistry and Biochemistry
University of Delaware
Five lab periods this semester will be devoted to an Independent Study. Your assignment is to devise a synthesis that you think would fit well in the second semester organic lab. This must be based on one or more articles from the research literature (usually the Journal of Organic Chemistry) , and you must have a plan for purifying and characterizing your intermediates. You can use as many as three steps, but two would be better. By way of illustration, raspberry flavor is 3, a crystalline ketone. There are at least four different ways one might imagine making 3 using reactions learned in first and second semester organic lecture. If your experiment works, you can publish it!
Choosing a project is your Chem 334 assignment for this first week! Please have your idea to me in writing, with a copy of the supporting article(s), by 10 a.m. Wednesday February 18th. That way, we will have time to talk about the projects, and make plans and order supplies. Be sure to keep a copy of your proposal for yourself. Please include your email address on your submission. Please note that each student will have a different project.
Please pay attention to the experimental procedures in the article that you choose. You are limited to a three-hour lab period, so a procedure that calls for heating overnight will not be acceptable. Most air-sensitive reagents (Buli, for instance) also would not be acceptable. Make sure also that the compounds you plan to make are not too volatile (low molecular weight) to isolate! Make sure that there is an Experimental to follow, and that the spectra are recorded in CDCl3.
Lab Work: After you run the first reaction, you will analyze your product mixture by thin layer chromatography, and purify your product by column chromatography. You will then record 1H NMR, 13C NMR and IR spectra for your chromatographed material. You will then use your purified material in the second step of your project. Again, you will analyze your product mixture by thin layer chromatography, and purify your product by column chromatography. Again, you will record 1H NMR, 13C NMR and IR spectra for your chromatographed material. Please include all spectra with each draft of your report.
Report: When you have completed your Independent Study, the last requirement is to create a formal written report. Please submit an initial draft by the end of the fourth day of the Independent Study, even though lab work is still going on. Write it on a word processor, so it is easy to correct. You can download ChemSketch to do the drawings, if you like. This should be a first-person, past tense narrative of what you did, what you observed, and what you concluded. I would also like your opinion as to whether or not the reactions that you did would be suitable to include in the undergraduate organic course. Please give your reasons, for and against, in detail.
Please use all of your writing skills as you draft this report. Use complete sentences, and begin each paragraph with a topic sentence. Please double space. Include copies of all spectra with each draft of the report. The original article(s) should also accompany the report each time. Be sure to put your name and email address on your report.
I will edit each draft and return it to you. You will then make the corrections and return the new version to me, along with the draft that was corrected. We will continue this process until the report is clear and understandable. I can be reached at Douglass F. Taber