Chem 263 - Lecture Outline & Assignment #1

Readings
Problems
Outline
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Readings:

TWG Solomons and CB Fryhle "Organic Chemistry" 11th Edition (2014):

Functional Group List on page 76
Periodic Table - Inside Front Cover (one page back from Inside Back Cover on earlier editions)
Relative Strength of Acids and Bases on Inside Front Cover
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 9.12
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 to 9.9 (both solved & review problems); 9.16; 9.23; 9.24

Chapter 13:
13.1 to 13.6 (both solved & review problems); 13.20; 13.25; 13.35; 13.40; 13.45

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

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
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
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
Electrocyclic Reactions of Alkene Systems
1. Diels-Alder and Retro Diels-Alder
  1. General Form of reaction
  2. Stereochemistry