Freshman Organic Chemistry II

Open Yale


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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.

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Reaction Rates
Bond Dissociation Energies
Relative Reactivities
Radical-Chain Reactions


Lecture 1 Mechanism: How Energies and Kinetic Order Influence Reaction Rates

Lecture 2 Peculiar Rate Laws, Bond Dissociation Energies, and Relative Reactivities

Lecture 3 Rate and Selectivity in Radical-Chain Reactions

Lecture 4 Electronegativity, Bond Strength, Electrostatics, and Non-Bonded Interactions

Lecture 5 Solvation, H-Bonding, and Ionophores

Lecture 6 Brønsted Acidity and the Generality of Nucleophilic Substitution

Lecture 7 Nucleophilic Substitution Tools - Stereochemistry, Rate Law, Substrate, Nucleophile, Leaving Group

Lecture 8 Solvent, Leaving Group, Bridgehead Substitution, and Pentavalent Carbon

Lecture 9 Pentavalent Carbon? E2, SN1, E1

Lecture 10 Cation Intermediates – Alkenes: Formation, Addition, and Stability

Lecture 11 Carbocations and the Mechanism of Electrophilic Addition to Alkenes and Alkynes

Lecture 12 Nucleophilic Participation During Electrophilic Addition to Alkenes: Halogen, Carbene, and Borane

Lecture 13 Addition to Form Three-Membered Rings: Carbenoids and Epoxidation

Lecture 14 Epoxide Opening, Dipolar Cycloaddition, and Ozonolysis

Lecture 15 Metals and Catalysis in Alkene Oxidation, Hydrogenation, Metathesis, and Polymerization

Lecture 16 Isoprenoids, Rubber, and Tuning Polymer Properties

Lecture 17 Alkynes; Conjugation in Allylic Intermediates and Dienes

Lecture 18 Linear and Cyclic Conjugation Theory; 4n+2 Aromaticity

Lecture 19 Aromatic Transition States: Cycloaddition and Electrocyclic Reactions

Lecture 20 Electronic and Vibrational Spectroscopy

Lecture 21 Functional Groups and Fingerprints in IR Spectroscopy; Precession of Magnetic Nuclei

Lecture 22 Medical MRI and Chemical NMR

Lecture 23 Diamagnetic Anisotropy and Spin-Spin Splitting

Lecture 24 Higher-Order Effects, Dynamics, and the NMR Time ScaleLecture 25 C-13 and 2D NMR – Electrophilic Aromatic Substitution

Lecture 26 Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg

Lecture 27 Triphenylmethyl and an Introduction to Carbonyl Chemistry

Lecture 28 Mechanism and Equilibrium of Carbonyl Reactions

Lecture 29 Imines and Enamines; Oxidation and Reduction

Lecture 30 Oxidation States and Mechanisms

Lecture 31 Periodate Cleavage, Retrosynthesis, and Green Chemistry

Lecture 32 Measuring Bond Energies: Guest Lecture by Prof. G. Barney Ellison

Lecture 33 Green Chemistry; Acids and Acid Derivatives

Lecture 34 Acids and Acid Derivatives

Lecture 35 Acyl Insertions and α-Reactivity

Lecture 36 α-Reactivity and Condensation Reactions

Lecture 37 Proving the Configuration of Glucose and Synthesizing Two Unnatural Products

Lecture 38 Review: Synthesis of Cortisone