Chemistry 4361/8361

Interpretation of Organic Spectra

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Lecture and Workshop Schedule


Date Lecture Topic Readings
Wed, Sep 5
Introduction

In-Class Exercise: Unsaturation Number

In-Class Exercise Solutions

Required: Lambert 1.1-1.5
Fri, Sep 7 NMR--Nuclear Spin and the NMR Phenomenon Required: Lambert 2.1-2.5
Recommended:
Claridge 1.1-2.3
Mon, Sep 10 NMR--Relaxation and the FID

In-Class Exercise: Using NMR to Analyze a Typical Chemical Reaction

In-Class Exercise Solutions

Required: Lambert 2.6-2.10
Wed, Sep 12 NMR--Chemical Shift, Equivalence, and Basic Splitting Patterns

In-Class Exercise: Basic Splitting Patterns in NMR

In-Class Exercise Solutions

Required: Lambert 3.1-3.6
Thurs, Sep 13
4:15-5:15 pm
Discussion Section, Smith 121

Discussion Section Exercise: Simple NMR Assignments

Discussion Section Exercise Solutions


Fri, Sep 14 NMR--Complex Splitting Patterns; The Karplus Equation; Long-Range Coupling

In-Class Exercise: Resonances with Multiple Coupling Constants

In-Class Exercise Solutions

Required: Lambert 4.1, 4.3-4.10
Mon, Sep 17 Workshop 1: Analyzing 1D NMR Spectra

Workshop 1 Solutions


Tues, Sep 18
4:15-5:15 pm
Discussion Section, Smith 121

Discussion Section Exercise: 1H NMR Multiplets with Different Coupling Constants

Discussion Section Exercise Solutions


Wed, Sep 19 NMR--More Complex Splitting Patterns; Multiplets at Low Dd/J
Problem Set 1 Due

In-Class Exercise: Deciphering Multiplets with Many J's

In-Class Exercise Solutions

Required:
T. Hoye, H. Zhao, J. Org. Chem. 2002, 67, 4014
T. Hoye, P. Hanson, J. Vyvyan, J. Org. Chem. 1994, 59, 4096
Fri, Sep 21 NMR--Chemical vs. Magnetic Inequivalence; Spin Decoupling

In-Class Exercise: 13C NMR Spectroscopy

In-Class Exercise Solutions

Required: Lambert 4.2, 5.3, 5.5
Recommended: Claridge 4.1-4.2
Mon, Sep 24 Workshop 2: Structure Determination w/ Complex 1D NMR

Workshop 2 Solutions


Tues, Sep 25
4:15-5:15 pm
Discussion Section, Smith 121

Discussion Section Exercise: Complex Splitting Patterns in 1H NMR

Discussion Section Exercise Solutions


Wed, Sep 26
NMR--Dynamics; Macromolecules; Chemical Shift Reagents
Problem Set 2 Due
Required: Lambert 5.1-5.2
Fri, Sep 28
NMR--Stereochemistry and Chiral Derivatizing Agents

In-Class Exercise: Resolving Stereochemistry with Mosher Esters

In-Class Exercise Solutions

Required:
J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512.
Recommended:

I. Ohtani et al., J. Am. Chem. Soc. 1991, 113, 4092.
Mon, Oct 1
NMR--Nuclear Overhauser Effect; Multiple Pulse Experiments; Inversion Recovery (Measuring T1)

In-Class Exercise: Spatial Relationships and 1D NOE

In-Class Exercise Solutions

Required: Lambert 5.4
Recommended:
Claridge 8.1-8.6, 2.4-2.5
Tues, Oct 2
4:15-5:15 pm
Discussion Section, Smith 121

Discussion Section Activity: Exam 1, Problem 2 from Fall 2002


Wed, Oct 3
Elliott N119
Exam 1
(Covers Sep 5-Sep 26)


Fri, Oct 5
No class.
(8361 Only: Rescheduled to Oct 26th)
 
Mon, Oct 8 NMR--Spin Echo Techniques (DEPT); 1D TOCSY

In-Class Exercise: DEPT-90 and DEPT-135

In-Class Exercise Solutions

Required: Lambert 5.6-5.8
Recommended: Claridge 4.3-4.5
Tues, Oct 9
4:15-5:15 pm
Discussion Section, Smith 121

No scheduled activity


Wed, Oct 10 NMR--Two-Dimensional NMR: COSY Techniques
Problem Set 3 Due

In-Class Exercise: 1H-1H (Homonuclear) COSY

In-Class Exercise Solutions

Required: Lambert 6.1
Recommended: Claridge 5.1-5.4
Fri, Oct 12 Workshop 3: Interpreting 2D COSY Spectra

Workshop 3 Solutions

8361 Only: Lab 1 Due
 
Mon, Oct 15 NMR--Two-Dimensional NMR: gCOSY, DQF-COSY, HMQC

In-Class Exercise: Heteronuclear Correlations in HMQC

In-Class Exercise Solutions

Required: Lambert 6.2
Recommended: Claridge 5.5-5.6, 6.1-6.3, 7.1-7.4
Tues, Oct 16
4:15-5:15 pm
Discussion Section, Smith 121

Discussion Section Exercise: 2-Dimensional NMR Spectroscopy

Discussion Section Exercise Solutions


Wed, Oct 17 NMR--Two-Dimensional NMR: HMBC, INADEQUATE
Problem Set 4 Due

In-Class Exercise: Multiple-Bond Correlations in HMBC

In-Class Exercise Solutions

Required: Lambert 6.4
Recommended: Claridge 5.7-5.9, 6.4-6.6
Fri, Oct 19 Workshop 4: Heteronuclear Correlations

Workshop 4 Solutions


Mon, Oct 22
NMR—Two-Dimensional NMR: 2D-J, 2D-TOCSY, NOESY

In-Class Exercise: Through-Space Correlations with 2D NOESY

In-Class Exercise Solutions

Required: Lambert 6.3
Recommended:
Claridge 7.1-7.4
Tues, Oct 23
4:15-5:15 pm
Discussion Section, Smith 121

Discussion Section Activity: Exam 2 from Fall 2011


Wed, Oct 24
Elliott N119
Exam 2
(Covers Sep 28-Oct 15)


Fri, Oct 26
8361 Only: NMR Facility Tour, Kolthoff 193 Recommended: Claridge 3.1-3.6
Mon, Oct 29
NMR--Two-Dimensional NMR: ROESY; IR--Techniques and Applications Recommended: Claridge 8.7-8.10
Tues, Oct 30
4:15-5:15 pm
Discussion Section, Smith 121

No scheduled activity


Wed, Oct 31
IR--Functional Groups; Raman Spectroscopy and Microscopy (Handouts from Oct 29)

Problem Set 5 Due

Required: Lambert 11.1-11.10, 12.1-12.19
Fri, Nov 2
UV-vis--Basic Principles, Functional Groups; Fluorescence Spectroscopy
Required: Lambert 13.1-13.5, 14.1-14.11
Mon, Nov 5
MS--Basic Principles
8361 Only: Lab 3 Due
Required: Lambert 7.1-7.2
Recommended: de Hoffmann 1.1-1.17
Tues, Nov 6
4:15-5:15 pm
Discussion Section, Smith 121

No scheduled activity


Wed, Nov 7
MS--Ion Sources
Problem Set 6 Due
 
Fri, Nov 9 MS--Mass Analyzers and Detectors Required: Lambert 7.3-7.4
Recommended: de Hoffmann 2.1-3.2

Mon, Nov 12 MS--Exact Masses, Isotope Patterns

In-Class Exercise: Halogen Isotope Patterns

In-Class Exercise Solutions

Required: Lambert 9.1-9.2
Recommended: de Hoffmann 6.1-6.7

Tues, Nov 13
4:15-5:15 pm
Discussion Section, Smith 121

Discussion Section Activity: Exam 3 from Fall 2011


Wed, Nov 14
Elliott N119
Exam 3
(Covers Oct 17-Nov 9)

Fri, Nov 16
8361 Only: MS Facility Tour, Kolthoff 193
Mon, Nov 19 MS--Radical Ion Fragmentation in Electron-Ionization MS

In-Class Exercise: Radical Cation Fragmentations in EI-MS

In-Class Exercise Solutions

Required: Lambert 8.1-8.10
Recommended: de Hoffmann 7.1-7.7
Reference:
McLafferty 4.1-9.12
Wed, Nov 21 MS--More Radical Ion Fragmentation

In-Class Exercise: Ketone Radical Cation Fragmentation

In-Class Exercise Solutions


Fri, Nov 23 Holiday.
Mon, Nov 25
Workshop 5: Fragmentation in EI-MS

Workshop 5 Solutions

 
Tues, Nov 26
4:15-5:15 pm
Discussion Section, Smith 121

Discussion Section Exercise: EI Fragmentation

Discussion Section Exercise Solutions


Wed, Nov 28
MS--Even-Electron Ion Fragmentation; Tandem Mass Spectrometry

In-Class Exercise: Collision-Induced Dissociation with Even-Electron Ions

In-Class Exercise Solutions

Required: Lambert 8.11
Recommended: de Hoffmann 4.1-5.3
Fri, Nov 30
Workshop 6: MS Analysis with Even-Electron Ions

Workshop 6 Solutions

 
Mon, Dec 3
MS--Mass Spectrometry of Macromolecules and Noncovalent Complexes; Ion Mobility Spectroscopy Required: Lambert 9.4
Recommended: de Hoffmann 8.1-8.6
Tues, Dec 4
4:15-5:15 pm
Discussion Section, Smith 121
Wed, Dec 5
Problem Set 7 Due (Can also be turned in Monday, Dec. 3)
Fri, Dec 7  
Mon, Dec 10
Elliott N119
Exam 4
(Covers Nov 7-Dec 5)

Wed, Dec 12 Return Exam 4, Course Evaluations
Sat, Dec 15
(1:30 pm - 3:30 pm)
Elliott N119

Final Exam
(Comprehensive)