Organic Structure Determination >> Content Detail



Amazon logo Help support MIT OpenCourseWare by shopping at! MIT OpenCourseWare offers direct links to to purchase the books cited in this course. Click on the Amazon logo to the left of any citation and purchase the book from, and MIT OpenCourseWare will receive up to 10% of all purchases you make. Your support will enable MIT to continue offering open access to MIT courses.

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
  3. C. HMBC
  4. D. NOESY and ROESY
  5. E. TOCSY

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


5.43 (Advanced Organic Chemistry) or permission of instructor.


None Required


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


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:

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


© 2009-2018, All Rights Reserved.
Higher Ed Space ® is a registered trademark of AmeriCareers LLC.