Freshman Organic Chemistry

Yale , Prof.J. Michael McBride

Communicating Molecular Structure in Diagrams and Words


Lecture Description

Freshman Organic Chemistry (CHEM 125)It is important that chemists agree on notation and nomenclature in order to communicate molecular constitution and configuration. It is best when a diagram is as faithful as possible to the 3-dimensional shape of a molecule, but the conventional Fischer projection, which has been indispensable in understanding sugar configurations for over a century, involves highly distorted bonds. Ambiguity in diagrams or words has led to multibillion-dollar patent disputes involving popular drugs. International agreements provide descriptive, unambiguous, unique, systematic "IUPAC" names that are reasonably convenient for most organic molecules of modest molecular weight.00:00 - Chapter 1. The Development of the Fischer Projections 16:27 - Chapter 2. Diastereomers and Enantiomers in van't Hoff's Brochure 23:14 - Chapter 3. Notation Ambiguities and Multibillion Dollar Pharmaceutical Disputes 39:26 - Chapter 4. The IUPAC and the Standardization of Molecular NomenclatureComplete course materials are available at the Open Yale Courses website: course was recorded in Fall 2008.

Course Description

How Do You Know – Force Laws, Lewis Structures and Resonance – Double Minima, Earnshaws Theorem and Plum – Puddings – Coping with Smallness and Scanning Probe Microscopy – X-Ray Diffraction-Seeing Bonds by Electron Difference Density – Quantum Mechanical Kinetic Energy – One-Dimensional Wave Functions – Chladni Figures and One – Electron Atoms – Reality and the Orbital Approximation – Orbital Correction and Plum – Pudding Molecules – Overlap and Atom – Pair Bonds – Overlap and Energy – Match – Checking Hybridization Theory with XH_3-Chemical Reactivity: SOMO, HOMO, and LUMO – Recognizing Functional Groups – Reaction Analogies and Carbonyl Reactivity – Amide, Carboxylic Acid and Alkyl Lithium-Oxygen and the Chemical Revolution – Rise of the Atomic Theory – Berzelius to Liebig and W�hler – Radical and Type Theories (1832-1850)-Valence Theory and Constitutional Structure (1858) – Determining Chemical Structure by Isomer Counting (1869)

Models in 3D Space (1869-1877); Optical Isomers – Vant Hoffs Tetrahedral Carbon and ChiralityCommunicating Molecular Structure in Diagrams and Words – Stereochemical Nomenclature; Racemization and Resolution – Preparing Single Enantiomers and the Mechanism of Optical Rotation – Esomeprazole as an Example of Drug Testing and Usage – Preparing Single Enantiomers and Conformational Energy – Stereotopicity and Baeyer Strain Theory -Conformational Energy and Molecular Mechanics – Sharpless Oxidation Catalysts and the Conformation of Cycloalkanes – Understanding Molecular Structure and Energy through Standard Bonds – Bond Energies, the Boltzmann Factor and Entropy – Potential Energy Surfaces, Transition State Theory and Reaction Mechanism

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