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Michael Evans
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003 Acidity and Basicity of Alcohols
003 Localized Molecular Orbitals and NBO Theory
003 Mechanisms of Catalysis
003 Oxidation Reactions of Thiols
003 Shorthand in Organic Structures
003 The Particular Building Blocks
004 Brønsted Acid Catalysis
004 Functional Groups
004 Hydroxide is a Poor Nucleofuge!
004 NBO Analysis of Methane
004 Three-dimensional Structures
005 Brønsted Base Catalysis
005 Electron Sources and Sinks
005 Electrostatic Potential Maps, Dipole Moments, and Partial Charges
005 Reactivity of Neutral Alcohols
005 Shapes of Natural Bond Orbitals
006 Molecular Geometry
006 Nucleophilic Catalysis: Michael Evans
006 Polarization and Relative Energies
006 Reactivity of Alkoxides
006 The Structural Determinants of Resonance
007 Classifying Atoms and Groups by Substitution Pattern
007 Insights Gained from Resonance Structures
007 Lewis Acid Catalysis
007 Orbital Interactions
007 Reactivity of Protonated Alcohols
008 Ester Hydrolysis and Specific Acid Catalysis
008 Introduction to Curved Arrows
008 Synthesis of Alcohols
009 Curved Arrows as Electronic Bookkeeping
009 General Acid Catalysis
009 Substitution Reactions of Alcohols
010 Base Catalysis and Summary
010 Sulfonate Esters: Electrophilic Derivatives of Alcohols
011 Enantioselective Catalysis
011 Formation of Sulfonate Esters from Alcohols
04.01 Structure and Nomenclature of Ethers
04.01 What Is Stability?
04.02 Reaction Coordinate Diagrams and Stability Trends
04.02 Reactivity of Ethers and Protonated Ethers
04.03 Stability Factors: Charge and Electronegativity
04.03 Syntheses of Ethers
04.04 Introduction to Epoxides
04.04 Stability Factors: Resonance Delocalization
04.05 Stability Factors: Hybridization
04.05 Syntheses of Epoxides
04.06 Stability Factors: Inductive Effects
04.06 Substitution Reactions of Epoxides
04.07 Stability Factors: Steric Effects
04.07 Thioethers
04.08 Relative Importance of Resonance Structures
05.01 Introduction to Conformation
05.01 Structure and Nomenclature of Amines
05.02 Basicity of Amines
05.02 Representing Conformation
05.03 General Reactivity of Amines
05.03 Potential Energy and Conformation
05.04 Conformational Analysis of Ethane and Bromoethane
05.04 Syntheses of Amines: Substitution Reactions
05.05 Conformational Analysis of 1,2-Dibromoethane
05.05 Syntheses of Amines: Reductions and Rearrangements
06.01 Conformations of Cycloalkanes: General Ideas
06.01 Structure of the Carbonyl Group
06.02 Exploring the Conformations of Cycloalkanes
06.02 Nomenclature of Carbonyl Compounds
06.03 Acidity and Basicity of Carbonyl Compounds
06.03 Conformations of Cyclohexane
06.04 General Reactivity of the Carbonyl Group
06.04 The Cyclohexane Ring Flip Process
06.05 Carboxylic Acid Derivatives
06.05 Monosubstituted Cyclohexanes
06.06 Disubstituted Cyclohexanes and Beyond
06.06 Nucleophilic Acyl Substitution
06.07 Two Classes of Carbonyl Compounds
07.01 Oxidation and Reduction in Organic Chemistry
07.01 Why is Chirality Important?
07.02 A Formal Definition of Chirality
07.02 Oxidation Numbers
07.03 Determining Whether a Molecule is Chiral
07.03 Oxidation Ladders
07.04 Configuration: Structure in Three Dimensions
07.04 Lithium Aluminum Hydride
07.05 Other Reductions by Lithium Aluminum Hydride
07.05 The Stereocenter
07.06 Naming Configurations
07.06 Sodium Borohydride
07.07 DIBAL-H, Di(isobutyl)aluminum hydride
07.08 Overview of Carbonyl Reductions
07.09 Oxidations in General
07.10 Strong Oxidations of Alcohols
07.11 Weak Oxidations and Pyridinium Chlorochromate
07.12 Swern Oxidation
07.13 Dess-Martin Periodinane
08.01 Acylation of Nucleophiles: Introduction and Biochemical Example
08.01 Isomerism: The Same and Not the Same
08.02 Diastereomerism
08.02 Nucleophilic Acyl Substitution Revisited
08.03 Addition-Elimination Equilibria
08.03 Enantiomerism
08.04 Catalysis in Acylation Reactions
08.04 Determining Isomeric Relationships
08.05 Energetics of Stereoisomerism
08.05 Overview of Acylation Reactions and Acyl Chlorides
08.06 Acylation by Anhydrides and Esters
08.07 Hydrolysis and Dehydration of Amides
08.08 Esterification of Carboxylic Acids
08.09 Activation Substitution of Carboxylic Acids
08.10 A Reactivity Map of Carboxylic Acid Derivatives
09.01 Additions of Heteroatomic Nucleophiles to Ketones and Aldehydes
09.01 Stereochemical Environments within a Molecule
09.02 Hydration of Ketones and Aldehydes
09.02 The Substitution Test for Stereotopic Relationships
09.03 Addition of Alcohols to Ketones and Aldehydes (Hemiacetal Formation)
09.03 Symmetry Elements
09.04 Acetal Formation
09.04 The Symmetry Elements Test
09.05 Acetals as Protecting Groups and Thioacetals
09.05 Energy and Heterotopic Group Selection
09.06 Addition of Amines to Ketohydes
09.06 How Chiral Objects Distinguish Between Enantiotopic Groups
09.07 Imine Formation
09.08 Enamine Formation
09.09 Nitrogen Analogues of Carbonyls and Derivatives
09.10 Reductive Amination
10.01 Organometallic Compounds
10.01 What Is Spectroscopy?
10.02 Introduction to Infrared Spectroscopy
10.02 Ligands in Organometallic Complexes
10.03 Fundamental Principles of IR: Bonds as Springs
10.03 Synthesis of Organometallic Compounds
10.04 General Reactivity of Organometallics
10.04 The Wavenumber Scale
10.05 Additions of Organolithiums and Grignard Reagents to Ketohydes
10.05 Regions of the Infrared Spectrum
10.06 Other Reactions of Organolithiums and Grignard Reagents with Carbonyl Compounds
10.07 Structure and Reactivity of Ylides
10.08 The Wittig Reaction
10.09 Stereochemistry of the Wittig Reaction
101 Acidity of Carbonyl alpha-Carbons
101 Fundamentals of Mass Spectrometry
101 Introduction to Aldol Additions
101 Nuclear Spin in a Magnetic Field
101 Nucleophilic Acyl Substitution by Enolates
101 Stereotopic Relationships, Chemical Shift, and Coupling
102 Aldol Condensations
102 Carbon-13 NMR Spectroscopy
102 Introducing the Claisen Condensation
102 Nuclear Magnetic Resonance
102 Structures of Molecular Ions
102 Trends in Carbonyl Acidity
103 Carbon-13 DEPT NMR Spectroscopy
103 Fragmentation Reactions
103 Introduction to Tautomerization; Stability of Keto and Enol Tautomers
103 Mechanism of the Claisen Condensation
103 The Pulsed NMR Method
103 Thermodynamics and Synthetic Utility of Aldol Reactions
104 Acid-catalyzed Aldol Condensations
104 Chemical Shift
104 Dieckmann Condensations and Crossed Claisen Condensations
104 Isotopic Abundance in Mass Spectrometry
104 Mechanisms of Tautomerization
104 Two-dimensional NMR Spectroscopy
105 Crossed and Directed Aldol Reactions
105 Fatty Acid Biosynthesis: Introduction and Condensation
105 General Reactivity of Enols and Enolates
105 Integration
105 Putting It All Together: Structure Determination
106 Bases for Enolate Formation
106 Coupling: Introduction and Coupling Constants
106 Fatty Acid Biosynthesis: Reduction and Fundamental Principles
106 Intramolecular Aldol Reactions
107 Coupling: Splitting Patterns and Spin Statistics
107 Halogenation of Enols and Enolates
108 Ester Enolates
108 Structure Determination from Proton NMR
108 The Mannich Reaction
109 Alkylation of Enolates
109 Carbonyl Reactions in Synthesis
110 Acetoacetic Ester Synthesis
111 Malonic Ester Synthesis
14.01 A Molecular Model of Chemical Equilibrium
14.01 alpha,beta-Unsaturated Carbonyl Compounds
14.02 1,2-Addition versus Conjugate Addition to Unsaturated Carbonyls
14.02 The Proton Transfer Elementary Step
14.03 Acidity and Basicity Constants
14.03 Examples of Conjugate Addition Reactions
14.04 Comparisons of Acidity: Quantitative Approach
14.04 The Michael Reaction
14.05 Comparisons of Acidity: Structural Approach
14.05 The Robinson Annulation
15.01 Foundational Skills for Working with Curved Arrows
15.01 Nitrogen Analogues of Carbonyls and Enols
15.02 The Mannich and Michael Reactions Revisited
15.03 Stork Enamine Reactions
15.04 Anilines, Pyrroles, and Pyridines: Heterocyclic Analogues of Enamines and Imines
15.05 Lewis Theory: Nucleophiles and Electrophiles
15.06 Elementary Steps as Orbital Interactions
15.07 Classes of Organic Reactions
16.01 The Elementary Steps: Introduction and Overview
16.02 Association of a Nucleophile
16.03 Dissociation of a Nucleofuge
16.04 Association of an Electrophile
16.05 Dissociation of an Electrofuge
16.06 1,2-Rearrangement
16.07 Nucleophilic Addition to a Polarized Pi Bond
16.08 Beta-elimination
16.09 Bimolecular Elimination
16.10 Bimolecular Nucleophilic Substitution
17.01 Thermodynamics and Kinetics
17.02 Drawing Transition States
17.04 Molecular Roles in Organic Reactions
17.05 The Most Reactive Starting Material Principle
17.06 Drawing Byproducts
17.07 Identifying Bonds Made and Broken
18.01 Definitions for Nucleophilic Substitution Reactions
18.02 Identifying the Nucleophile, Leaving Group, and Electrophile
18.03 What Makes a Good Leaving Group?
18.04 Predicting Products of Nucleophilic Substitution Reactions
18.05 Two Mechanisms of Nucleophilic Substitution
18.06 Bimolecular Nucleophilic Substitution: Mechanism and Stereochemistry
18.07 Unimolecular Nucleophilic Substitution: Mechanism and Stereochemistry
19.01 Predicting Mechanisms of Nucleophilic Substitution Reactions
19.02 Intramolecular Nucleophilic Substitutions
19.03 Proton-mediated Nucleophilic Substitution Reactions
19.04 Nucleophilic Substitution Reactions of Epoxides
19.05 Carbocation Rearrangements in Unimolecular Substitution Reactions
20.01 General Aspects of Elimination Reactions
20.02 Predicting Products of Elimination Reactions
20.03 Two Mechanisms of Elimination
20.04 Bimolecular Elimination: Mechanism and Stereochemistry
20.05 Unimolecular Elimination
20.06 Predicting Mechanisms of Elimination Reactions
201 Additions of Hydrohalic Acids
201 The Structures of Alkenes
202 General Aspects of Electrophilic Additions
202 Stereochemistry of Hydrohalogenation
203 Acid-catalyzed Hydration
203 Nucleophile
203 Site Selectivity and Stereoselectivity in Electrophilic Additions
204 Additions of Elemental Halogens
204 Nucleophile
204 Two General Mechanisms of Electrophilic Addition
205 Nucleophile
205 Stereochemistry of Halogenation
24.01 Hydroboration-oxidation
24.02 Oxymercuration
24.03 Electrophilic Epoxidation
25.01 General Aspects of Oxidation and Reduction
25.01 Introduction to Organic Synthesis
25.02 Hydrogenation of Alkenes
25.02 Retrosynthetic Analysis
25.03 Retrosynthesis of Demerol
25.03 syn-1,2-Dihydroxylation
25.04 Oxidative Cleavage
25.04 Synthesis of Demerol
25.05 Ozonolysis
25.05 Synthons
26.01 Introduction to Protecting Groups
26.02 Silyl Ethers as Protecting Groups
26.02 Stability Trends, Bond Dissociation Enthalpies, and Initiation
26.03 Acetals as Protecting Groups
26.03 Radical Chain Mechanisms: Overview and Initiation
26.04 Protecting Groups for Amines: Sulfonamides
26.04 Radical Chain Mechanisms: Propagation
26.05 Protecting Groups for Amines: Carbamates
26.05 Termination and Summary
26.06 Examples of Radical Reactions
27.01 Electron Donation and Withdrawal Revisited
27.01 Structure and Acidity of Alkynes
27.02 Electrophilic Additions to Alkynes
27.02 Resonance and Inductive Effects
27.03 Hammett Substituent Constants Defined
27.03 Hydrohalogenation of Alkynes
27.04 A Survey of Hammett Substituent Constants
27.04 Halogenation of Alkynes
27.05 Acid-catalyzed Hydration of Alkynes and Tautomerization
27.05 Linear Free-energy Relations: Applying Hammett Constants
27.06 Hydroboration and Oxymercuration of Alkynes
27.06 Mechanistic Insight from Hammett Studies
28.01 Radical Hydrohalogenation of Alkynes
28.02 Syn Hydrogenation of Alkynes
28.03 Anti Hydrogenation of Alkynes
28.04 Ozonolysis of Alkynes
28.05 Summary of Reactions of Alkynes
30.01 Structural Elements of Delocalized Pi Systems
30.02 Conjugation and Thermodynamic Stability
30.03 Molecular Orbitals of Delocalized Pi Systems
30.04 Electron-donating and -withdrawing Groups
30.05 Practice with Donating and Withdrawing Groups
30.06 Allylic Systems
30.07 Optical Properties of Conjugated Systems
301 Introduction to Aromatic Heterocycles
301 Nomenclature of Substituted Benzenes
301 The Structure of Benzene
302 Benzylic Systems
302 Molecular Orbitals and Resonance Structures of Benzene
302 Pyridine versus Pyrrole
303 Electron-rich and Electron-poor Heterocycles
303 Inductive Effects in Substituted Benzenes
303 Resonance Stabilization Energy of Benzene
304 A Survey of Heterocycles
304 Criteria for Aromaticity
304 Resonance Effects in Substituted Benzenes
305 Relative Strengths of Donating and Withdrawing Groups
305 Using Aromaticity and Antiaromaticity
306 Molecular Orbitals of Electronically Activated Benzenes
306 The Frost Circle
307 Polycyclic Aromatic Hydrocarbons and Annulenes
34.01 Introduction to Aromatic Reactions
34.02 Electrophilic Aromatic Substitution
34.03 Reaction Rates in Electrophilic Aromatic Substitution
34.04 Site Selectivity in Electrophilic Aromatic Substitution
34.05 Nucleophilic Aromatic Substitution
35.01 Halogenation of Benzene
35.02 Sulfonation of Benzene
35.03 Nitration of Benzene
35.04 Friedel-Crafts Alkylation
35.05 Friedel-Crafts Acylation
35.06 Benzylic Reduction Reactions
35.07 Reactions of Benzene Carbon Side Chains
36.01 Synthesis and Reactions of Arenediazonium Ions
36.02 Electrophilic Aromatic Substitutions of Substituted Benzenes
36.03 Directing Effects in Disubstituted Benzenes
36.04 Electrophilic Aromatic Substitutions of Heteroaromatics
36.05 Functional Group Interchange Reactions in Aromatic Synthesis
36.06 Practice with Multi-step Synthesis of Substituted Benzenes
37.01 Sandmeyer Reactions
37.02 Nucleophilic Aromatic Substitution of Electron-poor Benzenes
37.03 Nucleophilic Aromatic Substitution of Heteroarenes
37.04 Formation and Reactions of Benzynes
37.05 Birch Reduction
38.01 Introduction to Pericyclic Reactions
38.02 Selectivity Issues in the Diels-Alder Reaction
38.03 Diastereomers from the Diels-Alder Reaction: Endo versus Exo
38.04 Rate and Regioselectivity in Diels-Alder Reactions
38.05 Stereochemistry in Diels-Alder Reactions
38.06 The Endo Rule: Diastereoselectivity in the Diels-Alder Reaction
Acid-base Titration: Michael Evans
Aldolase Enzymes and the Nitro-aldol Reaction
Bomb Calorimetry: Michael Evans
cis-trans Isomerism: Michael Evans
Designing Buffer Solutions: Michael Evans
Diels-Alder Stereochemistry: Michael Evans
Draw the electron-pushing arrows of a reaction - YouTube
Draw the products of a reaction (inter- and intramolecular, and sigma bond migrations) - YouTube
Drawing Cyclohexane Chairs: Michael Evans
Drawing Lewis Structures: Michael Evans
Electron Configurations of Atoms: Michael Evans
Elements of Organic Chemistry and Periodic Trends
Entropy and Probability: Michael Evans
Factors Affecting Reaction Rate: Michael Evans
Fundamentals of Catalysis
Integrated Rate Laws: Michael Evans
Introduction to Aromatic Compounds: Michael Evans
Introduction to Buffers: Michael Evans
Introduction to Chemical Kinetics: Michael Evans
Introduction to Electrolysis: Michael Evans
Introduction to Hybridization: Michael Evans
Ionization Energy and Electron Affinity: Michael Evans
Kinetic Molecular Theory of Gases: Michael Evans
Learning Objectives: Michael Evans
M4
Nucleophilic Catalysis: Michael Evans
Organic Is Not Introductory Chemistry
Overview of reaction mechanisms - M1
Physical Properties and Intermolecular Forces
Problem Solving in Organic Chemistry
Proteins: Michael Evans
Radical Structures and "Fishhook" Curved Arrows
Reducing and Oxidizing Agents in Nature
Resonance: Michael Evans
Self-ionization of Water: Michael Evans
Sigma and Pi Bonding: Michael Evans
Structural Analogies: Michael Evans
Structure and Nomenclature of Alcohols
Structure and Nomenclature of Thiols
The Orbital Concept: Michael Evans
x 002 Atomic Orbitals and Hybridization
x 002 Hydrogen Bonding in Alcohols
x 002 Reactivity of Thiols and Thiolates
x 002 The Generalized Building Blocks
x 002 Transition States Revisited
Jumps
Chemical Principle 2: Michael Evans
Introductory Chemistry: Michael Evans
Organic Chemistry 2: Michael Evans
Organic Chemsistry 1: Michael Evans
Videos: Michael Evans