Claude E. Wintner
Organic Chemistry Reference Lectures
Video and Related Text
© 2000, 2002 Claude E. Wintner
Brief Biography of Professor Claude E. Wintner
Acknowledgment
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Lecture 1 -Introduction
Lecture 2 - Conformation
Lecture 3 - Constitution
Lecture 4 - Configuration
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4.01 Enantiomerism
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4.02 Introduction to CIP
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4.03 CIP Mechanics
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4.04 Diastereoisomerism: 3,4-Dimethylheptane
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4.05 Achiral Diastereoisomers: 3,4-Dimethylhexane
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4.06 A More Complicated Case: 3,4,5-Trimethylheptane
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Lecture 5 - Hydrocarbon Rings
Lecture 6 - Stereotopism
Lecture 7 - Carbon Bonding
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7.01 Hydrogen Molecule
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7.02 Csp3 Bonding - Methane
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7.03 Csp2 Bonding - Ethylene
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7.04 Csp2 Bonding - Ethylene, continued
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7.05 Csp Bonding - Acetylene
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7.06 Allene (1,2-Propadiene)
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7.07 Tau Bonds ("Bent Bonds")
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7.08 E/Z Nomenclature
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Lecture 8 - Bonding in Carbon Polyene Systems
Lecture 9 - Basic Ideas of Thermodynamics and Kinetics
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9.01 Simple Application of Gibbs' Equation
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9.02 Simple Application of Eyring's Equation
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9.03 Thermodynamic vs. Kinetic Control of a Reaction
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Lecture 10 - Functionality
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10.01 The Concepts Primary, Secondary, Tertiary
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Lecture 11 - Acidity and Basicity
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11.01 Aqueous Acids and Bases - pKA
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11.02 The Lewis Nucleophile-Electrophile Definition
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11.03 Avoiding Error When Invoking Aqueous Acids and Bases
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11.04 Potential Delocalization of an Anion Affects Acidity
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11.05 Kinetic vs. Thermodynamic (Equilibrium) Acidity
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11.06 Nucleophilicity vs. Basicity
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Lecture 12 - Oxidation and Reduction: Forms of Writing Reactions
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12.01 Balancing Redox Reactions
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12.02 Reduction of Alkenes - Forms of Writing Reactions
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12.03 Oxidation of Alkenes to Oxiranes (Epoxides)
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12.04 Oxidation of Alkenes to 1,2-Diols (Cis-Oxidation)
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12.05 Diastereoselectivity in Redox Reactions
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12.06 Enantioselectivity in Redox Reactions
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Lecture 13 - Bimolecular Nucleophilic Substitution and Elimination Reactions
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13.01 Bimolecular Nucleophilic Substitution
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13.02 The SN2 Mechanism
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13.03 The Special Case of Primary Halide Synthesis
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13.04 Steric Effects on the SN2 Mechanism
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13.05 The E2 Mechanism Competes with SN2
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13.06 Stereochemistry of the E2 Reaction
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13.07 Synthesis of Isopropyl Methyl Ether
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Lecture 14 - Unimolecular Nucleophilic Substitution and Elimination Reactions
Lecture 15 - Electrophilic Addition to Alkenes
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15.01 Addition of HX to Alkenes
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15.02 Acid Catalyzed Polymerization of Alkenes
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15.03 Epoxidation of cis-2-Butene
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15.04 Epoxidation of trans-2-Butene
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15.05 Bromination of Alkenes
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15.06 Stereochemistry of Bromine Elimination vs. Addition
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15.07 Electrophilic Aromatic Substitution
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Lecture 16 - Introduction to the Carbonyl Group
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16.01 Introduction to Carbonyl Bonding and Reactivity
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16.02 Introduction to Carbonyl Nomenclature
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16.03 Reaction of the Carbonyl Group with Electrophiles and with Nucleophiles
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16.04 Nucleophilic Addition to the Carbonyl Group vs. Nucleophilic Substitution at Carbonyl
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Lecture 17 - Alcohol Synthesis via Nucleophilic Addition to the Carbonyl Group
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17.01 Oxidation Reactions of Alcohols to Carbonyl Derivatives
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17.02 Reduction of Aldehydes and Ketones to Alcohols with LiAlH4 and NaBH4
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17.03 Grignard Reagents - Nucleophiles for Carbonyl Addition
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17.04 A General Synthesis of Alcohols
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17.05 Synthesis of 3-Hexanol
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17.06 Synthesis of 3-Methyl-3-Hexanol
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17.07 Diastereoselective Alcohol Syntheses and the Possibility of Enantioselective Alcohol Syntheses
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Lecture 18 - Further Nucleophilic Addition Reactions to the Carbonyl Group
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18.01 Hydrates
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18.02 Acetals and Ketals
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18.03 Imines, Oximes, Hydrazones
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18.04 Addition of Cyanide Anion to the Carbonyl and Imine Functionalities - a-Hydroxy Acids and a-Amino Acids
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Lecture 19 - Nucleophilic Substitution at the Carbonyl Group
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19.01 Carboxylic Acids - Formation and Activation
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19.02 Esters - Formation
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19.03 Esters - Hydrolysis and Transesterification
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19.04 Reactions of Esters with Grignard and Hydride Reagents
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19.05 Amides - Formation
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19.06 Amides - Hydrolysis
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19.07 Nitriles and their Hydrolysis to Amides and Carboxylic Acids - Tautomers
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Lecture 20 - Consequences of Hydrogen Acidity at Carbonyl a-Carbon - Aldol and Related Reactions
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20.01 Enolate and Enol
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20.02 Tau Bond Interpretation of Enolate Formation
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20.03 Aldol Condensation
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20.04 Aldol Condensation, Continued
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20.05 Claisen (Ester) Condensation - Dieckmann Condensation
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20.06 Alkylation and Decarboxylation of b-Ketoesters
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20.07 Uses of the Claisen
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20.08 Michael Reaction
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20.09 Robinson Annulation
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Lecture 21 - Brief Introduction to Carbohydrates
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21.01 Glucaric Acid is Chiral
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21.02 Ruff Degradation - Arabaric Acid is Chiral
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21.03 Kiliani Synthesis - Glucose and Mannose are C-2 Epimers
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21.04 Mannaric Acid is Chiral. Osazones
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21.05 Emil Fischer's Solution to the Glucose Problem
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21.06 Glucose Exists Predominantly in a Glucopyranose Ring
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21.07 Proof of Structure of 2,3,4,6-Tetramethylglucose
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21.08 How to Transform the Glucopyranose Structure into itsProper and Conventional Chair Conformational Rendering
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21.09 Furanose Rings
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21.10 Disaccharides - Lactose
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21.11 Polysaccharides - Cellulose and Starch
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Lecture 22 - Important General Subjects for Review
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22.01 The Concept of Retrosynthetic Analysis
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22.02 Writing Mechanisms in Organic Chemistry - The Notational Device of "Curved-Arrow Pushing"
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22.03 A Concluding Word
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All video segments ©2000 Claude E. Wintner