Syllabus

The following outline illustrates the major topics covered in the determination of organic structures.

I. Basics

A. Molecular Formula Determination (EA and MS)

1. Elemental Analysis (EA)
2. Mass Spectrometry (MS - EI)
3. Index of Hydrogen Deficiency (IHD)

B. Functional Groups (IR and NMR)

1. Infrared Spectroscopy (IR)
2. Nuclear Magnetic Resonance Spectroscopy (¹³C NMR)
3. Chemical Equivalence, Symmetry

C. Connectivity – Carbon-Hydrogen Framework (¹H NMR and MS)

1. ¹H NMR
   

   a. Chemical Equivalence and Non-equivalence
   b. Topicity
   c. Spin-spin Splitting (J Coupling)

   1. Signature Patterns
   2. Representative Values
      

   d. The Chemical Shift

   1. Trends, Representative values
   2. Estimation (Tables, Formulas, Computer Programs)
      
      
2. MS Fragmentation patterns
   

II. Advanced Methods and Topics

A. Advanced NMR Methods

1. ³¹P, ¹¹B, and other Nuclei
2. Through-bond Coupling
   
   a. DEPT/APT/INEPT
   b. ¹H–¹H Decoupling (1D) and COSY (2D)
   c. HMQC, HMBC, HSQC, INADEQUATE
   
   
3. Through-space Coupling

a. nOe (1D) and NOESY (2D)
b. ROESY

B. MS Methods

1. EI, CI, FAB, Negative Ion Modes, MALDI
2. GCMS, LCMS (APCI, Electrospray)
3. (MS)ⁿ

C. Stereochemistry

1. Determination of Configuration

   a. X-ray Crystallography
   b. CD-ORD
   c. Derivativization

2. Determination of Enantiomeric Excess
   
   a. [α]_D
   b. Chiral NMR Shift Reagents
   c. Chiral Stationary Phase Chromatography

Prerequisites

5.43 (Advanced Organic Chemistry) or permission of instructor.

Textbooks

Crews, Phillip, Jaime Rodríguez, and Marcel Jaspars. Organic Structure Analysis. New York: Oxford University Press, 1998. ISBN: 0195101022.

Pretsch, E., P. Bühlmann, and C. Affolter. Structure Determination of Organic Compounds: Tables of Spectral Data. Berlin; New York: Springer, 2000. ISBN: 3540678158.

Grading and Assignments

Your grade in this subject will be determined by the following (total of 400 points possible):