This class uses "gapped" lecture notes. The idea is that the tedious part of the note-taking is done for you, so that you spend less time writing in lecture, and more time listening and learning. The gaps represent those parts of the material that I think need to be emphasized, or that you need to learn how to to write and/or draw yourself. The gaps also help to keep you awake at 7:30 AM!

After we have finished each section of the notes in class, I will post my completed version so that you can make sure that you have no gaps or mistakes.

You must buy the "gapped" versions of the notes for this semester from the bookstore, notes from any previous semester of this course will not work for this semester, they have been changed.

On each midterm and final exam there will be one 5 pt. extra credit question that is taken from one of the "Real Life" links associated with each section of the notes.

  Completed Notes Useful Videos Review Videos "Real Life Topics"
1 Bonding I : Organic Molecular Structures •  Isomers (or lack of!)
•  Tetrahedral Geometry
•  Trigonal Planar Geometry
•  Linear Geometry
•  Pi-Bonds and Anti-Bonds
•  Visualizing the sigma- and pi-bonds in ethylene using the HGS model kit
•  Pi-Orbitals in Triple Bonds
•  Electron Energies and Ionization Energies
•  Working with Condensed, Lewis and Line-Angle Structures
•  Working A Problem in Structural Isomers
•  Formal Charges
•  Atomic Orbitals
•  VSEPR and Hybridization
•  VSEPR, Hybridization and Molecular Orbitals
•  Confused about the Whole Molecular Orbital Concept? A very Basic Review
•  Energies of Electrons in Molecules
•  Organic in My Real Life
•  Antibonding Orbitals
2 Bonding II : Organic Molecular Structures •  Rotation and Single Bonds
•  Isomerism and Double Bonds: Breaking the pi-Bond
•  Visualize Isomerization and Single Bonds
•  Visualize Isomerism and Double Bonds
•  Bond Rotation with a Model
•  Cis-/trans- Geometrical Isomers
•  Generating Lewis Structures from Molecular Formulae<
•  Another Short Review Session on Generating Lewis Structures from Molecular Formulae
•  Polar Bonds and their Molecular Orbitals
•  Dipole Moments
•  Very Short Review of Functional Groups
•  Organic in My Real Life
•  Antibonding Orbitals
3 Resonance : Delocalized Electrons   •  Basic, Simple Resonance Contributors
•  A More complete Review of Resonance
•  Confused about how and when to draw Minor resonance contributors?
•  Bond Dissociation Energies
•  A More Detailed Review of Bond Dissociation Energies
•  Quantum Mechanics
•  Resonance in Proteins
4 Alkanes : 3D Structures •  Introduction to Newman Projections
•  How to Use the HGS Model Kit
•  Rotation around a C-C Single bond and Newman Projections for Conformational Analysis
•  Rotation around a C-C Single bond in Propane
•  Steric versus Repulsion Effects in Alkane Conformations
•  Newman Projection to 3-D or Sawhorse Structure
•  Newman Projection to 3-D or Sawhorse Structure using a Model Kit
•  Chair-chair interconversion for cis-1,4-dimethylcyclohexane (with permission:Prof. Stefan Immel, TU Darmstadt)
•  Cyclohexane
•  Substituted Cyclohexane
•  Chair Interconversion Misconceptions
•  Building Cyclohexane Using a Model Kit
•  Chair-to-Chair Interconversion Using an HGS Model Kit
•  Alkane Nomenclature
•  Conformations of Acyclic (Linear) Alkanes
•  Conformations of Cyclic Alkanes
•  Burning
•  Rings
5 Organic Spectroscopy : Molecular Structure Determination •  Understanding the Factors that Control Bond Vibrations
Solving a Spectrum problem starting with molecular formula
Solving Another Spectrum problem starting with molecular formula
•  Understanding IR Spectroscopy
•  Interpreting and Assigning IR Spectra
•  Solving NMR Problems
•  Solving Combined IR/NMR Spectrum Problems
•  NMR and Medicine
•  Mass Spec at the Airport
6 Organic Reactions : How and Why Reactions "Go" •  Drawing Curved Arrows
•  Understanding Reaction Energy Diagrams
•  Bronsted Acid/Bases and acid/base Reactions
•  Lewis acid/base Reactions
An Introduction to Bronsted Acid/Base Reactions and how to learn them
•  Fastest Reactions
•  Acids and Bases
7 Alkenes : Introduction to Electrophilic Addition •  Backside Attack on a Bromonium Ion •  Alkene Properties and Stereochemistry
•  Alkene Nomenclature
•  Alkene Reactions
•  Alkene Mechanisms
•  An Introduction to Alkene Reactions and how to learn them
•  An Introduction to Alkene Mechanisms and how to learn them
•  Unsaturated Fats
•  Synthesis
8 Radical Reactions : Not Lewis acid/base reactions   •  Radical reactions and mechanisms •  Radicals and Health
•  Polymers
9 Chirality : Molecular "Handedness" •  Stereoisomers and the Superimposibility Test
•  The Two Enantiomers of Lactic Acid
•  Assigning Absolute Configuration (R/S) to the Enantiomers of Lactic Acid
•  Understanding Racemic Mixtures in Chemical Reactions
•  Determining configuration R/S using your hand
•  Determining configuration R/S using a model
•  Solving R/S problem #1
•  Solving R/S problem #2
•  Solving R/S problem #3
•  Solving R/S problem #4
•  Solving R/S problem #5
•  Short review of chiral centers, R/S and optical activity
•  Short review of optical activity (only!)
•  Short review on the various isomers, enantiomers, diastereomers, meso etc.
•  Short review on chirality and optical activity as related to chemical reactions
•  Hormones
•  Thalidomide
10 Halides : Substitution and Elimination •  The Walden Inversion
•  Stereochemistry and E2 elimination
•  SN1 versus SN2 reactions
•  E2 reactions
•  SN1 versus E1
•  SN1 vs SN2 vs E1 vs E2
•  Energy Diagrams in Substitutions and Eliminations
•  Ozone Layer
•  Substitution and Energy