This is a continuation of Freshman Organic Chemistry I (CHEM 125a), the introductory course on current theories of structure and mechanism in organic chemistry for students with excellent preparation in chemistry and physics. This semester treats simple and complex reaction mechanisms, spectroscopy, organic synthesis, and some molecules of nature.
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, Leaving Group
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: Halogen, Carbene, and Borane
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 α-Reactivity
α-Reactivity and Condensation Reactions
Proving the Configuration of Glucose and Synthesizing Two Unnatural Products
Review: Synthesis of Cortisone