CEM 845 Fall 2003

Organic Structural Elucidation by Instrumental Methods

Instructor: Greg Baker TA: Mercy Anyika

534 Chemistry 524 Chemistry

355-9715 x160 355-9715 x339

bakerg@msu.edu anyikame@chemistry.msu.edu

Class lecture: M 3:00-4:50 PM, WF 11:30 AM-12:20 PM in room 136, Chemistry

Course Description:

This course explores the relationships between organic functionality and the observed spectroscopic properties of organic molecules. These relationships are then used to rationally deduce the chemical structures of unknown organic molecules. Five methods, mass spectrometry, vibrational spectroscopy, electronic absorption spectroscopy, and chiroptical measurements will be applied in the structural assignment of unknown compounds. This is a practical course that emphasizes acquisition of the spectral data of unknown compounds, as well as the correlation of all available spectroscopic data to assign their structures. The molecular principles behind the measurements are discussed, and a variety of spectroscopic techniques are introduced.

Course Outline:

I. Mass Spectrometry

II. Ultraviolet/visible Spectroscopy

III. Infrared/Raman Spectroscopy

IV. NMR Spectroscopy

V. Chiroptical Methods

Course Texts:

Organic Structural Spectroscopy (J.B. Lambert, H.F. Shurvell, D.A. Lightner, R.G. Cooks; Prentice-Hall; 1998). (required)

Structure Determination of Organic Compounds - Tables of Spectral Data (E. Pretsch, P. Buhlmann, Martin Badertscher); Springer-Verlag; 2009) A compendium of spectral data, a key resource for structure determination. (required)

One-dimensional and Two-dimensional NMR Spectra by Modern Pulse Techniques (K. Nakanishi; University Science Books; 1990) (recommended)

Examinations, Homework, and Grading Scheme.

Grades will be based on the results of 4 homework assignments (20%), a midterm exam (25%), a final exam (35%) and timely completion of NMR training assignments (5%). The remaining 15% of your grade will be based on your determination of the structure of an unknown using the spectroscopic techniques used in the course. Since each unknown is different, the grading for this portion of the course emphasizes your application of logic and problem solving skills rather than simply getting the correct structure.

Exams will not be given during the normal class time. Instead, the exams will be scheduled for an evening or on a weekend to ensure that you will have ample time to finish the exam.

The due date for homework sets will be announced in class. Late homework (turned in after the end of class) will be subject to a 50% penalty for each day it is late.

Class notices / information will be sent by e-mail, via the class mailing feature of the msu e-mail system. If you normally use another account for e-mail, you should have your msu e-mail forwarded to that account. I will maintain “flexible office hours.” Simply e-mail me if you need to meet with me.

Other Resources

A partial list of spectroscopy-related books available in the Biophysical Sciences library:

Call number	Author	Title
QD 96.N8 B43 2000	Becker, E.D.	High resolution NMR : theory and chemical applications 3rd. ed.
QD 96.N8 B68 1988	Bovey, F.; Jelinski, L.; Mirau, P.	Nuclear Magnetic Resonance Spectroscopy
QD 96.N8 B73 1987	Breitmaier, E.; Voelter, W.	^13C NMR Spectroscopy methods and applications in organic chemistry and biochemistry
QD 272.S6 C43 1993	Chapman, J.R.	Practical Organic Mass Spectrometry: a guide for chemical and biochemical analysis
QD 272.S6 C5 1981	Clerc, J.; Pretsch, E.; Seibl, J.	Structural Analysis of Organic Compounds by Combined Application of Spectroscopic Methods
QD 272.S6 C66 1980	Cooper, J.W.	Spectroscopic Techniques for Organic Chemists
QD 481.E525 1994	Eliel, E.L.; Wilen; S.H.	Stereochemistry of Organic Compounds
QP 519.9 N83 E94 1995	Evans. J.N.S.	Biomolecular NMR Spectroscopy
QD 272.S6 S74 1995	Field, L.S.; Sternhell, S.; Kalman J.R.	Organic Structures From Spectra, 2^nd ed.,
QD 96.N8 G8313 1995	Gunther, H.	NMR Spectroscopy
QD 96 .N8 H37 1983	Harris, R.K.	Nuclear Magnetic Resonance Spectroscopy : a physicochemical view
QD 272.S6 K45 1991	Kemp, W.	Organic Spectroscopy, 3^rd ed.,
QD 272.S6 L54 1987	Lambert, J.B.; Shurvell, H.F.; Lightner, D.A.; Cooks, R.G.	Introduction to Organic Spectroscopy
QD 271.L34 1971	Laszlo, G.; Stang, P.	Organic Spectroscopy: Principles and Applications
QD 272.S6 L474 1980	Levy, G.; Lichter, R.; Nelson, G.L	Carbon-13 NMR Spectroscopy, 2^nd ed
QD 272.S6 M37 1983	Marshall, J.L.	Carbon-Carbon and Carbon-Proton NMR couplings: applications to organic stereochemistry and conformational analysis
QC 454.M3 M39 1993	McLafferty, F.W.; František Tureček	Interpretation of Mass Spectra, 4^th ed.
QD 481.M53 1965	Mislow, K.	Introduction to stereochemistry
QD 96.N8 O54 1990	Nakanishi, K.	One and Two-Dimensional NMR Spectra by Modern Pulse Techniques
QD 272.S6 O35 1985	Oki, M.	Applications of Dynamic NMR Spectroscopy to Organic Chemistry
QD 96.N8 R34 1986	Rahman, Atta-ur	Nuclear Magnetic Resonance : basic principles
QD 96.N8 S25 1987	Sanders, J.; Hunter, B.	Modern NMR spectroscopy : a guide for chemists
QP 519.9.M3 W37 1997	Watson, J.T.	Introduction to Mass Spectrometry 3^rd ed.,
QD 96.N8 W47 1987	Whitesell, J.K.; Minton, M.A.	Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy
QD 272.S6 W54 1980	Williams, D.H.; Fleming, I	Spectroscopic Methods in Organic Chemistry