Course Meeting Times
Lectures: 3 sessions / week, 1 hour / session
Outline and Overview of Topics
The following outline illustrates the major topics covered in the determination of organic structures.
I. Introduction: The tenets of assigning spectral features to molecular features
II. Features of the NMR spectrum
- A. Chemical shift
- B. Signal intensity
- C. Spin-spin coupling
III. NMR spectrum analysis
- A. Chemical shift prediction and interpretation
- B. Quantitation of signal strengths
- C. Deducing bond connectivity
IV. Advanced 1-D methods and concepts
- A. Spin gymnastics: APT and DEPT
- B. Selective decoupling
- C. Gated decoupling
- D. The Nuclear Overhauser Effect
- E. Fundamental limitations of 1-D methods
V. The second dimension
- A. Advantages associated with 2-D methods
- B. Caveats of 2-D
VI. Key 2-D experiments
- A. gCOSY
- B. HMQC/HSQC
- C. HMBC
- D. NOESY and ROESY
- E. TOCSY
- F. INADEQUATE
VII. Assignment strategies for a known compound
- A. Identification of entry points
- B. Good accounting practices
- C. Corroboration
VIII. Assignment strategies for an unknown compound
- A. Determination of molecular formula
- B. Identification of entry points
- C. Good accounting practices
- D. Parallel interpretations and Occam's razor
Prerequisites
5.43 (Advanced Organic Chemistry) or permission of instructor.
Textbooks
None Required
Recommended
Silverstein, R. M., F. X. Webster, and D. J. Kiemle. Spectrometric Identification of Organic Compounds. Hoboken, NJ: Wiley, 2005. ISBN: 9780471393627.
Recommended
Pretsch, E., P. Bühlmann, and C. Affolter. Structure Determination of Organic Compounds: Tables of Spectral Data. Berlin; New York: Springer, 2000. ISBN: 9783540678151.
Problem Sets
Problem sets will be assigned each time the class meets and will be due the following lecture.
Grading and Assignments
Your grade in this subject will be determined by the following:
ACTIVITIES | Percentage |
---|---|
Five problem sets | 15% |
Two in-class exams | 60% |
Final project: Determination of the structure of an unknown | 25% |