Courses:

Organic Structure Determination >> Content Detail



Syllabus



Syllabus

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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


  1. A. Chemical shift
  2. B. Signal intensity
  3. C. Spin-spin coupling


III. NMR spectrum analysis


  1. A. Chemical shift prediction and interpretation
  2. B. Quantitation of signal strengths
  3. C. Deducing bond connectivity


IV. Advanced 1-D methods and concepts


  1. A. Spin gymnastics: APT and DEPT
  2. B. Selective decoupling
  3. C. Gated decoupling
  4. D. The Nuclear Overhauser Effect
  5. E. Fundamental limitations of 1-D methods


V. The second dimension


  1. A. Advantages associated with 2-D methods
  2. B. Caveats of 2-D


VI. Key 2-D experiments


  1. A. gCOSY
  2. B. HMQC/HSQC
  3. C. HMBC
  4. D. NOESY and ROESY
  5. E. TOCSY
  6. F. INADEQUATE


VII. Assignment strategies for a known compound


  1. A. Identification of entry points
  2. B. Good accounting practices
  3. C. Corroboration


VIII. Assignment strategies for an unknown compound


  1. A. Determination of molecular formula
  2. B. Identification of entry points
  3. C. Good accounting practices
  4. D. Parallel interpretations and Occam's razor


Prerequisites


5.43 (Advanced Organic Chemistry) or permission of instructor.



Textbooks




None Required




Recommended


Amazon logo Silverstein, R. M., F. X. Webster, and D. J. Kiemle. Spectrometric Identification of Organic Compounds. Hoboken, NJ: Wiley, 2005. ISBN: 9780471393627.



Recommended


Amazon logo 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:


ACTIVITIESPercentage
Five problem sets15%
Two in-class exams60%
Final project: Determination of the structure of an unknown25%

 








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