Ch 340, Organic Spectroscopy

Winter, 2004 Class Schedule

O. McDougal: Office: Sc 266; Office Hrs: T 2-4, R 9-11, F 10-11 and by appointment; Phone: 552-6407; e-mail: mcdougao@sou.edu, or by appointment.

Text: D.L. Pavia, G.M. Lampman, G.S. Kriz, Introduction to Spectroscopy , 3 rd edition.

Week 1 Lab: Introduction to ¹H NMR spectra. To access dataset 1: CLICK HERE!

Tue: Introduction; Chapter 3 (3-1 to 3-4)

Thur: Proton Nuclear Magnetic Resonance Spectroscopy; Chapter 3 (3-5 to 3-11)

Week 2 Lab: Proton NMR interpretation, sample preparation, account activation, NMR tutorial. To access Data Set 2, CLICK HERE!

Tue: Coupling constants, nuclei, and experimental methods; Chapter 3 (3-12 to 3-19)

Thur: The chemical shift; Chapter 4

Week 3 Lab: Run ¹H & ¹³C spectra of your unknowns (You are limited to a maximum of one hour for the first week so that everyone can practice!  Use it wisely!)  You are encouraged to sign up with your instructor or a spectroscopy student mentor to prepare and run your first sample. Chemical shift calculations will be covered in lab, so bring your textbook with you. To access Data Set 3, CLICK HERE!

Tue: NMR instrumentation

Thur: The coupling constant; Chapter 5

Week 4 Lab: How to solve ¹H & ¹³C NMR spectral problems. Review for Midterm exam. REVIEW SHEET & SAMPLE MIDTERM

Tue: Compensation for overly optimistic presentation schedule!

Thur: NMR Spectral Problem Solving

Week 5 Lab: Learn how to run an IR.  Questions on NMR problem solving! To access Data Set 4, CLICK HERE! You will be doing chemical shift calculations for the remainder of the term, so please bring your textbook to all lab sessions.

Tue: Midterm Examination 2004

Thur: Infrared Spectroscopy Chapters 2 

Week 6 Lab:  Go over midterm exam. Run IR spectra of unknowns; combined spectral problem solving; Data Sets 1-4 have been updated to include all data (IR, MS, and NMR). To access Dataset 1, Dataset 2, Dataset 3, and Dataset 4, click on the appropriate link.

Tue: Infrared Spectroscopy Analysis Chapter 2; Reports containing the proton and carbon spectra and analysis are due for each of your unknown compounds.

Thur: IR Instrumentation and Spectra Chapter 2 continued

Week 7 Lab: Learn how to run a GC/MS; combined spectral problem solving. Present select compounds from datasets 1-4 to your peers. Overheads of spectra will be provided. Download dataset 5 HERE!

Tue: Mass Spectrometry; Chapter 8

Thur: Mass Spectrometry; Chapter 8

Week 8 Lab: Run spectra of unknowns (DEPT and HETCOR). Present your assigned problem from Dataset 5. Overheads will be provided of spectra. Download dataset 6 HERE!

Tue: Mass Spectrometry continued (Chapters 8).

Thur: MS Problem Solving/combined spectral problem solving (Chapter 9)

Week 9 Lab: Presentation Expectations and Signup!  Practice presentation and evaluation of assigned dataset 6 problems. Overheads of spectra will be provided. HELPFUL HINTS!

Tue:  NMR: 1D advanced topics (NOE difference and DEPT) (Chapter 10)

Thur:  NMR: 2D advanced topics (COSY, NOESY, TOCSY, HETCOR) (Chapter 10)

Week 10 Lab: Student Presentations!  Your PowerPoint presentations must be emailed to your lab instructor two days in advance.  You will lose 5 points per day your presentations are late.  They are worth 10 points!

Tue: Combined spectral problems!  REPORTS ARE DUE AT 1 p.m. AND THEY WILL NOT BE ACCEPTED LATE!

Thur: Final Exam Expectations!

Mar 17 In Class Final EXAM (1:00-3:00 pm)!

Grading: Grades will be based upon the total number of points accumulated, modified as necessary by my perception of the quality of your preparation for and participation in class activities. Points will be assigned for the midterm examination (100 points), the final examination (200 points), the preliminary unknown reports (30 points each), and the final presentation/written report (50 points each).

Unknowns: The laboratory portion of the course requires that you obtain spectra and write reports for two unknown compounds. These represent the purest compounds available to us, but are not guaranteed to be 100% free of impurities. If you believe your unknown is impure, consult with the instructor. We have made an effort to avoid giving out carcinogenic or otherwise hazardous compounds, but most organic compounds are toxic to some degree, so handle your unknowns with care. It is best to keep them in the lab, rather than carry them around with you.

Instrument Operation: Since there is only one of each instrument, it will often be necessary to obtain your spectra at times other than your scheduled laboratory period. Each instrument has a sign-up sheet showing when it is available during each week. You are expected to actually show up for times you have reserved. Points will be deducted for abuse of the system. Each instrument also has a log book which you must sign each time you use it. Points will be deducted for missing logbook entries. If the instrument behaves strangely, or you knowingly break something, let your instructor know immediately. There are no penalties for non-malicious events, and we need to get the instrument up and running again as soon as possible.

It is very much to your advantage to obtain the spectra of your unknowns as early as possible. This allows more time to analyze the results, discover any problems with your sample, and also allows you to avoid the inevitable crush of students desperately (and often unsuccessfully) trying to obtain spectra just before the deadline. You should also note that these instruments occasionally break down, generally during periods of intense student use at the last moment. Students who do not obtain spectra in time are usually afforded little or no sympathy.

This year we will have you sign-up to acquire spectra with your lab instructor or a spectroscopy mentor.  You will be given a review of how to operate the instrumentation and will then do so while supervised.  The NMR, GC-MS, and IR are new and we hope to minimize needless abuse of the instrumentation.  You will have an individual to assist you with any difficulty you may have in acquiring your data.

Unknown Reports/Presentations: You must write one preliminary report analyzing the proton and carbon NMR spectra for each unknown sample.  If overdue, reports will be penalized at the rate of 5 points per day.  See the web site for an example of what is expected in the reports.  The final lab evaluation is based on one written report and one oral presentation.  If you received a lower grade for one preliminary report than the other, you are required to rewrite the worse of the two reports.  The final report will include the proton and carbon NMR data, the IR spectrum, the GC-MS spectrum, and your interpretation of these data including a final structure of your unknown.  If you received grades of equal value on your preliminary reports, you can choose which report to finalize and which compound to discuss orally with your peers.  The final presentation will include the proton and carbon NMR spectra, the mass spectrum, and the infrared spectrum.  You will be given a maximum of ten minutes to convince your classmates that you have obtained the correct structure for your unknown compound.  You will be evaluated on five criteria, each of which is worth 10 points.  1.) Presentation quality overheads turned in two days prior to your presentation 2.) Analysis of proton/carbon NMR data 2.) Analysis of GC/MS and IR data 3.) Correct determination of your structure 4.) Presentation style, organization, and level of preparation (maximum length 10 minutes per unknown)!  Needless to say, it is essential that you rehearse your presentation to keep your total time to at or under 10 minutes. Please note that presentations that are updated will not be loaded from a floppy disc the day of the presentation. If it absolutely must be updated, you will surrender 10 of the 50 points possible.