Organic Chemistry Video Lessons

Ch. 1 - A Review of General Chemistry

Intro to Organic Chemistry Atomic Structure Wave Function Molecular Orbitals Sigma and Pi Bonds Octet Rule Bonding Preferences Formal Charges Skeletal Structure Drawing Correct Bondline Structures Lewis Structure Condensed Structural Formula Empirical Formulas Degrees of Unsaturation Isomer Constitutional Isomers Intro to Stereoisomers How to Recognize Cis and Trans Isomers Drawing Isomers Resonance Structures Resonance of Radicals Resonance Hybrids Major and Minor Resonance Contributors Hybridization Molecular Geometry Molecular Geometry with Resonance 3D Hybrid Orbital Drawings The CHM 7 Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond Cumulative General Concepts

Ch. 2 - Molecular Representations

Intermolecular Forces London Dispersion Force Van Der Waals How To Determine Solubility Hydrophilicity Functional Groups Carbonyl Amine Amide Drawing Isomers with Functional Groups

Ch. 3 - Acids and Bases

Organic Chemistry Reactions Reaction Mechanism Predicting Chemical Reactivity Nucleophiles and Electrophiles Acids and Bases Acid and Base Conjugates Give the conjugate acid for each compound below Equilibrium Constant Calculating Equilibrium Constants Using pKa pKa Acid Base Equilibrium Ranking Acidity Element Effect Resonance Effect Inductive Effect Hybridization Effect Steric Effects Acid and Base Equilibrium with ARIO Predicting Protonation Sites Lewis Acids and Bases Lewis Acid-Base Reactions Acid and Base Synthesis

Ch. 4 - Alkanes and Cycloalkanes

IUPAC Naming Alkyl Groups Complex Substituent Nomenclature Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Naming Cycloalkanes Naming Bicyclic Compounds Spiro Bicyclic Nomenclature Advanced Bicyclic Nomenclature Naming Alkyl Halides Naming Alkenes Alkene Nomenclature Alkyne Nomenclature Alkyne Substituent Common Nomenclature Naming Alcohols Naming Amines Cis and Trans Nomenclature Cis vs Trans Conformational Isomers Newman Projections Drawing Newman Projections Dihedral Angle Barrier To Rotation Newman Projections to Bondline Structures Newman Projections Explain s-trans Hydrocarbon Bonds Newman Projections of Rings Ring Strain Axial vs Equatorial Cis vs Trans Conformations Equatorial Preference Chair Flip Calculating Energy Difference Between Chair Conformations A-Values Cyclohexane - Newman Projections Decalin Catalytic Hydrogenation of Alkenes Alkane Combustion

Ch. 5 - Chirality

Constitutional Isomers vs. Stereoisomers Chirality Test 1: Plane of Symmetry Test 2: Stereocenter Test R and S Configuration Enantiomers vs. Diastereomers Predicting Chirality Determining Total Number of Stereoisomers Atropisomers Meso Compound Test 3: Disubstituted Cycloalkanes What is the Relationship Between Isomers? Fischer Projection R and S of Fischer Projections R and S of Newman Projections Racemic Mixture Optical Activity Enantiomeric Excess Calculations with Enantiomeric Percentages Non-Carbon Chiral Centers Cumulative Chirality Questions Prochirality Enantiomeric Separation by Diastereoisomeric Salts Enantiomeric Separation by Enzymes Enantiomeric Separation by Chiral Chromatography Achiral

Ch. 6 - Thermodynamics and Kinetics

Energy Diagram Gibbs Free Energy Enthalpy Entropy Chemical Equilibrium Kinetics Hammond Postulate Hyperconjugation Carbocation Stability Rank the following carbocations in order of decreasing stability Carbocation Intermediate Rearrangements Carbanion Stability

Ch. 7 - Substitution Reactions

Alkyl Halide Nucleophilic Substitution Good Leaving Groups Physical Properties of RX SN2 Reaction SN1 reaction Ion Pairing Effects Substitution Comparison

Ch. 8 - Elimination Reactions

E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Anti-Coplanar Requiring Rotation E2 - Cumulative Practice E1 Reaction Solvents Leaving Groups Nucleophiles and Basicity Rate Calculations Rate Calculations of Competitive Mechanisms SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination Substitution/Elimination Retrosynthesis Intramolecular Substitution/Elimination Practice The E1cb Mechanism

Ch. 9 - Alkenes and Alkynes

Alkene Stability Zaitsev Rule Dehydrohalogenation Hofmann Elimination of Alkyl Fluorides Debromination Double Elimination Acetylide Isomerization of Alkynes Hydrogenation of Alkynes Dissolving Metal Reduction Mechanism Hydrogenation Retrosynthesis Dehydration Reaction POCl3 Dehydration Alkynide Synthesis Alkynide Retrosynthesis Bredt's Rule

Ch. 10 - Addition Reactions

Addition Reaction Thermodynamics of Addition-Elimination Equilibria Markovnikov Stereospecificity vs. Stereoselectivity Hydrohalogenation Sulfonation Acid-Catalyzed Hydration Oxymercuration Oxymercuration-Reduction Full Mechanism Hydroboration Hydroboration-Oxidation Full Mechanism Alkoxymercuation Hydrogenation Halogenation Interhalogenation Halohydrin Haloether Formation Carbene Simmons-Smith Addition Mechanism Epoxidation Epoxide Reactions Regiospecificity of Acid-Catalyzed Ring Openings Anti Vicinal Dihydroxylation Dihydroxylation Ozonolysis Ozonolysis Full Mechanism Ozonolysis Retrosynthesis Oxidative Cleavage Alkyne Oxidative Cleavage Alkyne Hydrohalogenation Alkyne Halogenation LiBr and Acetic Acid for Anti Vinyl Dihaldes Alkyne Hydration Alkyne Hydroboration Addition Reagent Facts Predicting Stereoisomers of Addition Reactions Addition Missing Reagent Addition Synthesis Addition Texas Two-Step Addition Multi Step Addition Retrosynthesis Addition to Concave vs. Convex Rings

Ch. 11 - Radical Reactions

Radical Reaction Radical Stability Free Radical Halogenation Radical Selectivity Isomers of Radical Halogenation Calculating Radical Yields Anti Markovnikov Addition of Br Radical Hydrohalogenation of Alkynes Free Radical Polymerization Allylic Bromination Alkyl Halide Radical Reduction Ether Autooxidation Cyclopropane as a Nucleophile Radical Disproportionation Radical Texas Two-Step Radical Synthesis Radical Retrosynthesis

Ch. 12 - Alcohols, Ethers, Epoxides and Thiols

Hydroxyl Group Acidity/Basicity of Alcohols Active Metals as bases on Alcohols Alcohol Nomenclature Naming Ethers Crown Ether Nomenclature Cyclic Ether Nomenclature Naming Epoxides Naming Thiols Alcohol Synthesis Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Retrosynthesis Leaving Group Conversions Summary Physical Properties of Ethers Williamson Ether Synthesis Making Ethers - Alkoxymercuration Making Ethers - Alcohol Condensation Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Williamson Ether Retrosynthesis Synthesis of Phenol Ethers Ether Cleavage Cleavage of Phenyl Ethers Alcohol Protecting Groups t-Butyl Ether Protecting Groups Silyl Ether Protecting Groups Sharpless Epoxidation Acidity of Thiols Thiol Reactions Sulfide Oxidation Disulfide Reduction

Ch. 13 - Alcohols and Carbonyl Compounds

Oxidizing and Reducing Agents Calculating Oxidation States Oxidizing Agent Swern Oxidation Dess–Martin Periodinane (DMP) Oxidation Reducing Agent Reduction Mechanisms LiAlH4 Redox Retrosynthesis Oxidation with Bleach (HOCl) Glycol Cleavage (Periodic Acid - HIO4) Ketone and Aldehyde Hydroboration Alcohol Reduction Reduction of Epoxides with LAH Nucleophilic Addition Preparation of Organometallics Grignard Reaction Gilman Reactions Organometallic Synthesis Organometallic Retrosynthesis Protecting Alcohols from Organometallics Organometallic Cumulative Practice Organometallic Roadmaps

Ch. 14 - Synthetic Techniques

Synthetic Cheatsheet Moving Functionality Alkynide Alkylation Alkane Halogenation Retrosynthesis

Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect

Purpose of Analytical Techniques Infrared Spectroscopy Infrared Spectroscopy Table IR Spect: Frequencies Considering Solution Effects IR Spect: Drawing Spectra IR Spect: Extra Practice IR Spect: Structure Determination NMR Spectroscopy 1H NMR: Number of Signals 1H NMR: Q-Test 1H NMR: E/Z Diastereoisomerism H NMR Table 1H NMR: Spin-Splitting (N + 1) Rule 1H NMR: Spin-Splitting Simple Tree Diagrams 1H NMR: Spin-Splitting Complex Tree Diagrams 1H NMR: Spin-Splitting Patterns NMR Integration 1H NMR: Proton Exchange 1H NMR: Fast Proton Exchange (D2O) NMR Practice Carbon NMR 13C NMR: Cumulative Practice 2D NMR - COSY Structure Determination without Mass Spect Mass Spectrometry Mass Spect: Fragmentation Mass Spect: McLafferty Rearrangement Mass Spect: Isotopes Structure Determination with Mass Spect

Ch. 16 - Conjugated Systems

Diene Conjugation Chemistry Stability of Conjugated Intermediates Allylic Halogenation Conjugated Hydrohalogenation (1,2 vs 1,4 addition) Conjugated Halogenation Diels-Alder Reaction Diels-Alder Inductive Effects Diels-Alder Forming Bridged Products Diels-Alder Regiospecficity Diels-Alder Asymmetric Induction Diels-Alder Synthesis Diels-Alder Retrosynthesis Molecular Orbital Theory Drawing Atomic Orbitals Drawing Molecular Orbitals HOMO LUMO Orbital Diagram: 3-atoms- Allylic Ions Allylic SN1 and SN2 Orbital Diagram: 4-atoms- 1,3-butadiene Orbital Diagram: 5-atoms- Allylic Ions Orbital Diagram: 6-atoms- 1,3,5-hexatriene Orbital Diagram: Excited States Cumulative Orbital Diagram Problems Pericyclic Reaction Thermal Cycloaddition Reactions Photochemical Cycloaddition Reactions Cumulative Cycloaddition Reactions Thermal Electrocyclic Reactions Photochemical Electrocyclic Reactions Cumulative Electrocyclic Problems Sigmatropic Rearrangement Cumulative Sigmatropic Problems Cope Rearrangement Claisen Rearrangement UV-Vis Spect Basics UV-Vis Spect Beer's Law Molecular Electronic Transition Therory Woodward-Fieser Rules

Ch. 17 - Aromaticity

Aromaticity Physical Properties of Arenes Resonance Model of Benzene Huckel's Rule Pi Electrons Aromatic Hydrocarbons Annulene Aromatic Heterocycles Cumulative Aromaticity Problems Frost Circle Naming Benzene Rings Polycyclic Aromatic Hydrocarbon Nomenclature Acidity of Aromatic Hydrocarbons Basicity of Aromatic Heterocycles Ionization of Aromatics

Ch. 18 - Reactions of Aromatics: EAS and Beyond

Electrophilic Aromatic Substitution Benzene Reactions EAS: Halogenation Mechanism EAS: Nitration Mechanism EAS: Sulfonation Mechanism EAS: Friedel-Crafts Alkylation Mechanism EAS: Friedel-Crafts Acylation Mechanism EAS: Gatterman–Koch Reaction EAS: Any Carbocation Mechanism EAS: Total Benzene Isomers EAS: Polycyclic Aromatic Hydrocarbons Electron Withdrawing Groups EAS: Directing Effects Resonance Theory of EAS Directing Effects EAS: Badass Activity Chart EAS: Ortho vs. Para Positions Activated Benzene and Polysubstitutions Acylation of Aniline Limitations of Friedel-Crafts Alkyation Advantages of Friedel-Crafts Acylation Clemmensen Reduction Blocking Groups - Sulfonic Acid EAS: Synergistic and Competitive Groups EAS: Dueling Benzenes Side-Chain Halogenation Side-Chain Oxidation Hydrogenation of Benzene Birch Reduction EAS: Sequence Groups EAS: Missing Reagent EAS: Synthesis EAS: Retrosynthesis Diazonization of Aniline Diazo Replacement Reactions Diazo Coupling Reactions Diazo Sequence Groups Diazo Retrosynthesis Nucleophilic Aromatic Substitution Benzyne SNAr vs. Benzyne Aromatic Missing Reagent Aromatic Synthesis Aromatic Retrosynthesis EAS on 5-membered Heterocycles

Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition

Physical Properties of Ketones and Aldehydes Naming Aldehydes Naming Ketones Multi-Functionalized Carbonyl Nomenclauture Oxidizing and Reducing Agents Oxidation of Alcohols Ozonolysis Catalytic Reduction of Carbonyls DIBAL Tollens’s Test Fehling’s Test  Alkyne Hydration Alkyne Hydroboration to Yield Aldehydes Nucleophilic Addition Nucleophilic Addition Reactivity Cyanohydrin Strecker Synthesis Organometallics on Ketones Overview of Nucleophilic Addition of Solvents Hydrates Hemiacetal Acetal Acetal and Hemiacetal Acetal Protecting Group Synthesis Involving Acetals Thioacetal Imine vs Enamine Addition of Amine Derivatives Wolff Kishner Reduction Reduction of Carbonyls to Alkanes Clemmensen vs Wolff-Kischner Baeyer-Villiger Oxidation Baeyer-Villiger Oxidation Synthesis Acid Chloride to Ketone Weinreb Ketone Synthesis Nitrile to Ketone Wittig Reaction Wittig Retrosynthesis Horner–Wadsworth–Emmons Reaction Ketone and Aldehyde Synthesis Reactions Carbonyl Missing Reagent Carbonyl Hydrolysis Carbonyl Synthesis Carbonyl Retrosynthesis Reactions of Ketenes Ketene Synthesis

Ch. 20 - Carboxylic Acid Derivatives: NAS

Carboxylic Acid Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Mechanism Nucleophilic Acyl Substitution Reactivity Acidity of Carboxylic Acids Chemoselective Carboxylic Acid Reduction Naming Carboxylic Acids Diacid Nomenclature Ester Naming Esters Naming Nitriles Acid Chloride Nomenclature Naming Anhydrides Naming Amides Carboxylic Acid Derivative Nomenclature Multi-Functionalized COOH Nomenclauture Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride DCC Coupling Agent to Promote Amide Formation Dehydration of Amide Hydrolysis of Nitrile Esters via SN2 Reactions Methyl Esters Via Diazomethane Fischer Esterification Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Lactones, Lactams and Cyclization Reactions Organometallics on Esters Organometallics on Carboxylates Carboxylation Decarboxylation Mechanism Carboxylic Acid Missing Reagent Carboxylic Acid Synthesis Carboxylic Acid Retrosynthesis

Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon

Tautomerization Tautomers of Dicarbonyl Compounds Tautomers of Heteroatomic Compounds Enolate Alpha-Carbon Racemization Acid-Catalyzed Alpha-Halogentation Base-Catalyzed Alpha-Halogentation Haloform Reaction Hell-Volhard-Zelinski Reaction Amino-Acids via HVZ Overview of Alpha-Alkylations and Acylations Enolate Alkylation and Acylation Enolate Alkylation Synthesis Carboxylate Alkylation Enamine Alkylation and Acylation Enamine Retrosynthesis Beta-Dicarbonyl Synthesis Pathway Acetoacetic Ester Synthesis Malonic Ester Synthesis Beta-Dicarbonyl Retrosynthesis Activated Methylenes Alpha-Carbon Texas Two-Step Alpha-Carbon Cumulative Retrosynthesis Dithianes

Ch. 22 - Condensation Chemistry

Condensation Reactions Aldol Condensation Directed Condensations Crossed Aldol Condensation Claisen-Schmidt Condensation Aldol Retrosynthesis Claisen Condensation Claisen Retrosynthesis Intramolecular Aldol Condensation Intramolecular Condensation Retrosynthesis Knoevenagel Reaction Mixed Condensations Conjugate Addition Michael Addition Acid-Catalyzed Michael Reaction Michael Addition Retrosynthesis Alpha and Beta Alkylation Robinson Annulation Robinson Annulation Retrosynthesis Mannich Reaction Cannizzaro Reaction Hydrolysis Condensation Texas Two-Step Cumulative Condensation Reactions

Ch. 23 - Amines

Physical Properties of Amines Chirality of Amines Amine Basicity Amine Acidity Amine Alkylation Gabriel Synthesis Amines by Reduction Nitrogenous Nucleophiles Reductive Amination Curtius Rearrangement Hofmann Rearrangement Isocyanate Reactions Hofmann Elimination Cope Elimination Nitrosation of Secondary Amines Amine Synthesis Amine Retrosynthesis

Ch. 24 - Carbohydrates

Monosaccharide Monosaccharides - D and L Isomerism R and S of Sugars Monosaccharides - Drawing Fischer Projections Monosaccharides - Erythro and Threo Isomerism Monosaccharides - Common Structures Monosaccharides - Common Ketoses Monosaccharides - Forming Cyclic Hemiacetals Monosaccharides - Cyclization Monosaccharides - Pyranose-Furanose Isomerization Monosaccharides - Haworth Projections Mutarotation Epimerization Monosaccharides - Aldose-Ketose Rearrangement Monosaccharides - Overview of Reactions Monosaccharides - Alkylation Monosaccharides - Acylation Monosaccharides - Cyclic Acetals Glycoside Monosaccharides - O-Glycoside Hydrolysis Monosaccharides - N-Glycosides Monosaccharides - Reduction (Alditols) Monosaccharides - Weak Oxidation (Aldonic Acid) Reducing Sugars Monosaccharides - Strong Oxidation (Aldaric Acid) Monosaccharides - Oxidative Cleavage Monosaccharides - Osazones Monosaccharides - Kiliani-Fischer Monosaccharides - Wohl Degradation Monosaccharides - Ruff Degradation Disaccharide Polysaccharide

Ch. 25 - Phenols

Phenol Nomenclature Phenol Acidity

Ch. 26 - Amino Acids, Peptides, and Proteins

Proteins and Amino Acids Amino Acid Nomenclature L and D Amino Acids Polar Amino Acids Amino Acid Chart Peptide Bond Acid-Base Properties of Amino Acids Isoelectric Point