Chem 263 - Lecture Outline & Assignment #1

Readings
Problems
Outline
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Readings:

TWG Solomons and CB Fryhle "Organic Chemistry" 8th Edition (2004):

• Functional Group List on pp 70-71
• Periodic Table - one page back from Inside Back Cover
• Relative Strength of Acids and Bases on Inside Front Cover - same table page 105
• Chemical Shift Ranges in NMR – inside back cover facing page 
• Chapter 9 - Nuclear Magnetic Resonance (NMR) Spectroscopy
  • read all for overview
  • study sections 9.1 to 9.11
• Chapter 13 - Conjugated Unsaturated Systems

Problems:

Do Not turn in, answers available in "Study Guide and Solutions Manual for Organic Chemistry" by Solomons and Fryhle.

Chapter 9:
9.1; 9.2; 9.4; 9.5; 9.7; 9.8; 9.11; 9.36

Chapter 13:
13.1 to 13.7; 13.9; 13.12; 13.13; 13.14; 13.29; 13.32

Lecture Outline 1: Nuclear Magnetic Resonance (NMR) Spectroscopy, Conjugated Systems and Ultraviolet Spectroscopy

1. Nuclear Magnetic Resonance (NMR) Spectroscopy
   
   
   1. Electromagnetic Spectrum
      
      
   2. Principle of NMR and Instrumentation
      
      
   3. Proton Chemical Shift: Peak Position and Integration
      
      1. Shielding and Deshielding of Hydrogens – Chemical Shifts
      2. Tetramethylsilane (TMS) standard
      3. Equivalent and Non-equivalent Hydrogens
         
         
   4. Spin-Spin Splitting
      
      
   5. Basics of Carbon-13 NMR Spectroscopy
      
      
   6. Basics of 2D NMR Spectroscopy
      
      
      
2. Conjugated Systems and Resonance
   
   
   1. Nomenclature of Dienes and Allyl vs Vinyl
      
      
   2. Allyl Radical, Cation, and Anion - Stabilization  and Resonance
      
      
   3. Addition Reactions of Dienes
      
      
   4. Allylic Radicals and Allylic Cations - Rubber and Polystyrene
      
      
      
      
3. Energy Characteristics of Allylic Systems
   
   
   1. Stability of Conjugated Dienes
      1. Bond Lengths
      2. Conformation
         
         
   2. Visible and Ultraviolet Spectroscopy
      1. Measurement of spectra
      2. Absorption energies
      3. Biological significance
         
         
         
4. Electrocyclic Reactions of Alkene Systems
   
   
   1. Diels-Alder and Retro Diels-Alder
      1. General Form of reaction
      2. Stereochemistry