Mechanism: How Energies and Kinetic Order Influence Reaction Rates – Peculiar Rate Laws, Bond Dissociation Energies, and Relative Reactivities – Rate and Selectivity in Radical-Chain Reactions – Electronegativity, Bond Strength, Electrostatics, and Non-Bonded Interactions – Solvation, H-Bonding, and Ionophores – Brønsted Acidity and the Generality of Nucleophilic Substitution – Nucleophilic Substitution Tools – Stereochemistry, Rate Law, Substrate, Nucleophile – Solvent, Leaving Group, Bridgehead Substitution, and Pentavalent Carbon – Pentavalent Carbon? E2, SN1, E1 – Cation Intermediates. Alkenes: Formation, Addition, and Stability – Carbocations and the Mechanism of Electrophilic Addition to Alkenes and Alkynes – Nucleophilic Participation During Electrophilic Addition to Alkenes – Addition to Form Three-Membered Rings: Carbenoids and Epoxidation.
Epoxide Opening, Dipolar Cycloaddition, and Ozonolysis – Metals and Catalysis in Alkene Oxidation, Hydrogenation, Metathesis, and Polymerization – Isoprenoids, Rubber, and Tuning Polymer Properties – Alkynes. Conjugation in Allylic Intermediates and Dienes – Linear and Cyclic Conjugation Theory. 4n+2 Aromaticity – Aromatic Transition States: Cycloaddition and Electrocyclic Reactions – Electronic and Vibrational Spectroscopy – Functional Groups and Fingerprints in IR Spectroscopy. Precession of Magnetic Nuclei – Medical MRI and Chemical NMR – Diamagnetic Anisotropy and Spin-Spin Splitting – Higher-Order Effects, Dynamics, and the NMR Time Scale.
C-13 and 2D NMR. Electrophilic Aromatic Substitution – Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg – Triphenylmethyl and an Introduction to Carbonyl Chemistry – Mechanism and Equilibrium of Carbonyl Reactions – Imines and Enamines. Oxidation and Reduction – Oxidation States and Mechanisms – Periodate Cleavage, Retrosynthesis, and Green Chemistry – Measuring Bond Energies: Guest Lecture by Prof. G. Barney Ellison – Green Chemistry. Acids and Acid Derivatives – Acids and Acid Derivatives – Acyl Insertions and [gr]α-Reactivity – [gr]α-Reactivity and Condensation Reactions – Proving the Configuration of Glucose and Synthesizing Two Unnatural Products – Review: Synthesis of Cortisone.
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