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CHEM 125b

Freshman Organic Chemistry II

Undergraduate · Historical course

Spring 2011

Topics

  • 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

Readings

  • Reading assignments, problem sets, PowerPoint presentations, and other resources for this course can be accessed from Professor McBride's on-campus course website, which was developed for his Spring 2011 students: https://webspace.yale.edu/chem125
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  • Optional Text: Organic Chemistry , 4th edition, Maitland Jones, Jr. and Steven A. Fleming, W. W. Norton & Company, New York, 2010.
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Sources