Freshman Organic Chemistry

Yale , Prof.J. Michael McBride

Communicating Molecular Structure in Diagrams and Words

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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: http://open.yale.edu/coursesThis 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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