Organic Chemistry Wade • 7th Edition • 978-0321592316

Ch.1 - Introduction and Overview (Part 1)

Intro to Organic Chemistry Atomic Structure Octet Rule Bonding Preferences Formal Charges Skeletal Structure Lewis Structure Condensed Structural Formula Degrees of Unsaturation Constitutional Isomers

Ch.1 - Introduction and Overview (Part 2)

Resonance Structures Electronegativity Organic Chemistry Reactions Reaction Mechanism Acids and Bases Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity

Ch.2 - Structure and Properties of Organic Molecules

Wave Function Molecular Orbitals Sigma and Pi Bonds Hybridization Molecular Geometry Intermolecular Forces How To Determine Solubility Functional Groups

Ch.3 - Structure and Stereochemistry of Alkanes

IUPAC Naming Alkyl Groups Naming Cycloalkanes Naming Bicyclic Compounds Conformational Isomers Newman Projections Drawing Newman Projections Barrier To Rotation Ring Strain Axial vs Equatorial Cis vs Trans Conformations Chair Flip Equatorial Preference Calculating Energy Difference Between Chair Conformations A-Values Decalin

Ch.4 - The Study of Chemical Reactions

Radical Reaction Radical Stability Free Radical Halogenation Energy Diagram Gibbs Free Energy Enthalpy Entropy Radical Selectivity Hammond Postulate Calculating Radical Yields

Ch.5 - Stereochemistry

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 Optical Activity Enantiomeric Excess Calculations with Enantiomeric Percentages Non-Carbon Chiral Centers

Ch.6 - Alkyl Halides: Substitution (Part 1)

Naming Alkyl Halides Nucleophilic Substitution Good Leaving Groups Allylic Bromination SN2 Reaction SN1 Reaction Solvents Leaving Groups Nucleophiles and Basicity Carbocation Stability Carbocation Intermediate Rearrangements Substitution Comparison

Ch.6 - Alkyl Halides: Elimination (Part 2)

E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Cumulative Practice E1 Reaction SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination Alkene Stability Zaitsev Rule Radical Synthesis

Ch.7 - Structure and Synthesis of Alkenes

Naming Alkenes Cis vs Trans Alkene Stability Zaitsev Rule Dehydrohalogenation Dehydration Reaction

Ch.8 - Reactions of Alkenes

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

Ch.9 - Alkynes

Dehydrohalogenation Double Elimination Acetylide Nucleophilic Addition Hydrogenation of Alkynes Alkyne Halogenation Alkyne Hydrohalogenation Alkyne Hydration Alkyne Hydroboration Alkyne Oxidative Cleavage Alkynide Synthesis

Ch.10 - Structure and Synthesis of Alcohols

Naming Alcohols Alcohol Nomenclature Phenol Acidity Alcohol Synthesis Nucleophilic Addition Preparation of Organometallics Grignard Reaction Organometallic Cumulative Practice Oxidizing and Reducing Agents Reducing Agent Naming Thiols Thiol Reactions Sulfide Oxidation

Ch.11 - Reactions of Alcohols

Oxidizing and Reducing Agents Oxidation of Alcohols Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Dehydration Reaction POCl3 Dehydration Fischer Esterification

Ch. 12 - Infrared Spectroscopy and Mass Spect

Purpose of Analytical Techniques Infrared Spectroscopy Infrared Spectroscopy Table IR Spect: Drawing Spectra IR Spect: Extra Practice Mass Spectrometry Mass Spect: Fragmentation Mass Spect: Isotopes

Ch. 13 - Nuclear Magnetic Resonance

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 Structure Determination without Mass Spect NMR Practice Carbon NMR

Ch. 14 - Ethers, Epoxides and Sulfides

Naming Ethers Naming Epoxides Naming Thiols Williamson Ether Synthesis Making Ethers - Alcohol Condensation Making Ethers - Alkoxymercuration Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Ether Cleavage Silyl Ether Protecting Groups Epoxidation Epoxide Reactions

Ch. 15 - Conjugated Systems

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

Ch. 16 - Aromatic Compounds

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. 17 - Reactions of Aromatic Compounds

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 Limitations of Friedel-Crafts Alkyation Advantages of Friedel-Crafts Acylation EAS: Synergistic and Competitive Groups Side-Chain Halogenation Birch Reduction Side-Chain Oxidation EAS: Sequence Groups EAS: Retrosynthesis Nucleophilic Aromatic Substitution Benzyne Cross-Coupling General Reactions Heck Reaction Suzuki Reaction

Ch. 18 - Aldehydes and Ketones

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

Ch. 19 - Amines

Naming Amines Hofmann Elimination Cope Elimination Acylation of Aniline Diazo Replacement Reactions Diazo Sequence Groups Diazo Retrosynthesis Amine Alkylation Gabriel Synthesis Amines by Reduction Nitrogenous Nucleophiles Reductive Amination Curtius Rearrangement

Ch. 20 - Carboxylic Acids

Carboxylation Naming Carboxylic Acids Diacid Nomenclature Carboxylic Acid Derivatives Fischer Esterification (Simplified) DIBAL

Ch. 21 - Carboxylic Acid Derivatives

Naming Esters Acid Chloride Nomenclature Naming Anhydrides Naming Nitriles Naming Amides Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Fischer Esterification Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Lactones, Lactams and Cyclization Reactions Carboxylic Acid to Acid Chloride Grignard Reaction

Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds

Tautomerization Tautomers of Dicarbonyl Compounds Enolate Overview of Alpha-Alkylations and Acylations Enolate Alkylation and Acylation Enamine Alkylation and Acylation Beta-Dicarbonyl Synthesis Pathway Acetoacetic Ester Synthesis Malonic Ester Synthesis Decarboxylation Mechanism Acid-Catalyzed Alpha-Halogentation Base-Catalyzed Alpha-Halogentation Haloform Reaction Hell-Volhard-Zelinski Reaction Condensation Reactions Aldol Condensation Directed Condensations Crossed Aldol Condensation Claisen Condensation Intramolecular Aldol Condensation Conjugate Addition Michael Addition Robinson Annulation

Ch. 23 - Carbohydrates and Nucleic Acids

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. 24 - Amino Acids, Peptides, and Proteins

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