CEM 311 handouts

You are expected to be able to construct and interpret Lewis structures, including understanding their geometric implications.
You need to be intimately familiar with these general trends in acidity.
- One reason you need to be familiar with acidity trends is that basicity is inversely correlated with leaving group ability.
- Gas Phase Studies of the Competition between Substitution and Elimination Reactions, S. Gronert, Acc. Chem. Res. 2003, 36, 848-857
  This elegant series of experiments untangles intrinsic nucleophilicity and basicity from medium effects by running reactions in the gas phase. It considers both the nucleophile's strength as a Brønsted base and the structure of the substrate.
Lewis acids in organic chemistry
Values of Hammet constants σ, σ⁺ and σ^- for various groups, taken from J.E. Leffler and E. Grunwald, Rates and Equilibria of Organic Reactions, Wiley 1963 (Dover reprint)

For deep background, read Gimarc, B.M. "Applications of Qualitative Molecular Orbital Theory," Acc. Chem. Res. 1974, 7, 384-392, or his book, Molecular Structure and Bonding: The Qualitative Molecular Orbital Approach, Academic Press (1979).
Article considering various levels of bonding theory to explain Why doesn't carbon form a molecule with four covalent bonds?
Article on antibonding orbitals
Article on hybridization and electronegativity
Article comparing the valence-bond and molecular-orbital theories' descriptions of CO and SO₄
Article explaining Why is carbon the only element to link in long chains?
Article explaining why we call a molecule with two unpaired electrons a "triplet" in terms of the Pauli Exclusion Principle.
Lecture slides on valence-bond vs. molecular orbital bonding theories (PDF).
π molecular orbitals of conjugated poly-enes (useful for thinking about pericyclic reactions)
Pericyclic reactions with molecular models
- Conrotatory ring-opening of cyclobutenes
- Disrotatory ring-closing of conjugated trienes
- Diels-Alder reactions