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Organic Chemistry Concept Videos

Organic Chemistry Video Lessons

Concept, example, and practice videos to guide you through the topics in your specific textbook.

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 Lewis Structure Condensed Structural Formula Degrees of Unsaturation Isomer Constitutional Isomers Resonance Structures Hybridization Molecular Geometry Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond

Ch. 2 - Molecular Representations

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

Ch. 3 - Acids and Bases

Organic Chemistry Reactions Reaction Mechanism Acids and Bases Give the conjugate acid for each compound below Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity Lewis Acids and Bases

Ch. 4 - Alkanes and Cycloalkanes

IUPAC Naming Alkyl Groups Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Naming Cycloalkanes Naming Bicyclic Compounds Naming Alkyl Halides Naming Alkenes Naming Alcohols Naming Amines Cis vs Trans Conformational Isomers Newman Projections Drawing Newman Projections Barrier To Rotation Ring Strain Axial vs Equatorial Cis vs Trans Conformations Equatorial Preference Chair Flip Calculating Energy Difference Between Chair Conformations A-Values Decalin

Ch. 5 - Chirality

Constitutional Isomers vs. Stereoisomers Chirality Test 1: Plane of Symmetry Test 2: Stereocenter Test R and S Configuration Enantiomers vs. Diastereomers Atropisomers Meso Compound Test 3: Disubstituted Cycloalkanes What is the Relationship Between Isomers? Fischer Projection R and S of Fischer Projections Racemic Mixture Optical Activity Enantiomeric Excess Calculations with Enantiomeric Percentages Non-Carbon Chiral Centers Achiral

Ch. 6 - Thermodynamics and Kinetics

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

Ch. 7 - Substitution Reactions

Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison

Ch. 8 - Elimination Reactions

E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Cumulative Practice E1 Reaction Solvents Leaving Groups Nucleophiles and Basicity SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination

Ch. 9 - Alkenes and Alkynes

Alkene Stability Zaitsev Rule Dehydrohalogenation Double Elimination Acetylide Hydrogenation of Alkynes Dehydration Reaction POCl3 Dehydration Alkynide Synthesis

Ch. 10 - Addition Reactions

Addition Reaction Markovnikov Hydrohalogenation Acid-Catalyzed Hydration Oxymercuration Hydroboration Hydrogenation Halogenation Halohydrin Carbene Epoxidation Epoxide Reactions Dihydroxylation Ozonolysis Ozonolysis Full Mechanism Oxidative Cleavage Alkyne Oxidative Cleavage Alkyne Hydrohalogenation Alkyne Halogenation Alkyne Hydration Alkyne Hydroboration

Ch. 11 - Radical Reactions

Radical Reaction Radical Stability Free Radical Halogenation Radical Selectivity Calculating Radical Yields Anti Markovnikov Addition of Br Free Radical Polymerization Allylic Bromination Radical Synthesis

Ch. 12 - Alcohols, Ethers, Epoxides and Thiols

Hydroxyl Group Alcohol Nomenclature Naming Ethers 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 Summary Williamson Ether Synthesis Making Ethers - Alkoxymercuration Making Ethers - Alcohol Condensation Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Ether Cleavage Alcohol Protecting Groups t-Butyl Ether Protecting Groups Silyl Ether Protecting Groups Sharpless Epoxidation Thiol Reactions Sulfide Oxidation

Ch. 13 - Alcohols and Carbonyl Compounds

Oxidizing and Reducing Agents Oxidizing Agent Reducing Agent LiAlH4 Nucleophilic Addition Preparation of Organometallics Grignard Reaction Protecting Alcohols from Organometallics Organometallic Cumulative Practice

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: Drawing Spectra IR Spect: Extra Practice 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 NMR Practice Carbon NMR Structure Determination without Mass Spect Mass Spectrometry Mass Spect: Fragmentation Mass Spect: Isotopes

Ch. 16 - Conjugated Systems

Diene Conjugation Chemistry Stability of Conjugated Intermediates Allylic Halogenation Conjugated Hydrohalogenation (1,2 vs 1,4 addition) Diels-Alder Reaction Diels-Alder Forming Bridged Products Diels-Alder Retrosynthesis Molecular Orbital Theory Drawing Atomic Orbitals Drawing Molecular Orbitals HOMO LUMO Orbital Diagram: 3-atoms- Allylic Ions 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 Pericyclic Reaction Thermal Cycloaddition Reactions Photochemical Cycloaddition Reactions Thermal Electrocyclic Reactions Photochemical Electrocyclic Reactions Cumulative Electrocyclic Problems Sigmatropic Rearrangement Cope Rearrangement Claisen Rearrangement

Ch. 17 - Aromaticity

Aromaticity Huckel's Rule Pi Electrons Aromatic Hydrocarbons Annulene Aromatic Heterocycles Frost Circle Naming Benzene Rings 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: Friedel-Crafts Alkylation Mechanism EAS: Friedel-Crafts Acylation Mechanism EAS: Any Carbocation Mechanism Electron Withdrawing Groups EAS: Ortho vs. Para Positions Acylation of Aniline Limitations of Friedel-Crafts Alkyation Advantages of Friedel-Crafts Acylation Blocking Groups - Sulfonic Acid EAS: Synergistic and Competitive Groups Side-Chain Halogenation Side-Chain Oxidation Birch Reduction EAS: Sequence Groups EAS: Retrosynthesis Diazo Replacement Reactions Diazo Sequence Groups Diazo Retrosynthesis Nucleophilic Aromatic Substitution Benzyne

Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition

Naming Aldehydes Naming Ketones Oxidizing and Reducing Agents Oxidation of Alcohols Ozonolysis DIBAL Alkyne Hydration Nucleophilic Addition Cyanohydrin Organometallics on Ketones Overview of Nucleophilic Addition of Solvents Hydrates Hemiacetal Acetal Acetal and Hemiacetal Acetal Protecting Group Thioacetal Imine vs Enamine Addition of Amine Derivatives Wolff Kishner Reduction Baeyer-Villiger Oxidation Acid Chloride to Ketone Nitrile to Ketone Wittig Reaction Ketone and Aldehyde Synthesis Reactions

Ch. 20 - Carboxylic Acid Derivatives: NAS

Carboxylic Acid Carboxylic Acid Derivatives Naming Carboxylic Acids Diacid Nomenclature Ester Naming Esters Naming Nitriles Acid Chloride Nomenclature Naming Anhydrides Naming Amides Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Fischer Esterification Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Lactones, Lactams and Cyclization Reactions Carboxylation Decarboxylation Mechanism

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

Tautomerization Tautomers of Dicarbonyl Compounds Enolate Acid-Catalyzed Alpha-Halogentation Base-Catalyzed Alpha-Halogentation Haloform Reaction Hell-Volhard-Zelinski Reaction Overview of Alpha-Alkylations and Acylations Enolate Alkylation and Acylation Enamine Alkylation and Acylation Beta-Dicarbonyl Synthesis Pathway Acetoacetic Ester Synthesis Malonic Ester Synthesis

Ch. 22 - Condensation Chemistry

Condensation Reactions Aldol Condensation Directed Condensations Crossed Aldol Condensation Claisen-Schmidt Condensation Claisen Condensation Intramolecular Aldol Condensation Conjugate Addition Michael Addition Robinson Annulation Hydrolysis

Ch. 23 - Amines

Amine Alkylation Gabriel Synthesis Amines by Reduction Nitrogenous Nucleophiles Reductive Amination Curtius Rearrangement Hofmann Rearrangement Hofmann Elimination Cope Elimination

Ch. 24 - Carbohydrates

Monosaccharide Monosaccharides - D and L Isomerism Monosaccharides - Drawing Fischer Projections Monosaccharides - Common Structures Monosaccharides - Forming Cyclic Hemiacetals Monosaccharides - Cyclization Monosaccharides - Haworth Projections Mutarotation Epimerization Monosaccharides - Aldose-Ketose Rearrangement Monosaccharides - Alkylation Monosaccharides - Acylation Glycoside 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 Acidity

Ch. 26 - Amino Acids, Peptides, and Proteins

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

Ch. 26 - Transition Metals

Electron Configuration of Elements Coordination Complexes Ligands Electron Counting The 18 and 16 Electron Rule Cross-Coupling General Reactions Heck Reaction Stille Reaction Suzuki Reaction Sonogashira Coupling Reaction Fukuyama Coupling Reaction Kumada Coupling Reaction Negishi Coupling Reaction Buchwald-Hartwig Amination Reaction Eglinton Reaction

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