Organic Chemistry: Structure and Function Vollhardt • 6th Edition • 978-1429204941

Ch.1 - Structure & Bonding in Organic Molecules (Part 1)

Intro to Organic Chemistry Atomic Structure Wave Function Molecular Orbitals Sigma and Pi Bonds Octet Rule Bonding Preferences Formal Charges Skeletal Structure

Ch.1 - Structure & Bonding in Organic Molecules (Part 2)

Lewis Structure Condensed Structural Formula Degrees of Unsaturation Constitutional Isomers Resonance Structures Hybridization Molecular Geometry Electronegativity

Ch.2 - Structure (Part 1)

Intermolecular Forces How To Determine Solubility Functional Groups IUPAC Naming Alkyl Groups Conformational Isomers Newman Projections Drawing Newman Projections Barrier To Rotation

Ch.2 - Reactivity (Part 2)

Energy Diagram Gibbs Free Energy Enthalpy Entropy Reaction Mechanism Acids and Bases Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity

Ch.3 - Reactions of Alkanes

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

Ch.4 - Cycloalkanes

Naming Cycloalkanes Ring Strain Axial vs Equatorial Cis vs Trans Conformations Chair Flip Equatorial Preference Calculating Energy Difference Between Chair Conformations A-Values Decalin

Ch.5 - Stereoisomers

Constitutional Isomers vs. Stereoisomers Chirality Test 1: Plane of Symmetry Test 2: Stereocenter Test R and S Configuration Enantiomers vs. Diastereomers 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 - Properties and Reactions of Haloalkanes

Naming Alkyl Halides Nucleophilic Substitution Good Leaving Groups SN2 Reaction Solvents Leaving Groups Nucleophiles and Basicity

Ch.7 - Further Reactions of Haloalkanes

Carbocation Stability SN1 Reaction Substitution Comparison E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Cumulative Practice E1 Reaction SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination

Ch.8 - Alcohols

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

Ch.9 - Further Reactions of Alcohols and Ethers

Carbocation Stability Carbocation Intermediate Rearrangements Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Naming Ethers Naming Epoxides Naming Thiols 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 Epoxidation Epoxide Reactions Thiol Reactions Sulfide Oxidation

Ch. 10 - Nuclear Magnetic Resonance

Purpose of Analytical Techniques NMR Spectroscopy 1H NMR: Number of Signals 1H NMR: Q-Test 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

Ch.11 - Alkenes: Infrared Spectroscopy and Mass Spect

Degrees of Unsaturation Naming Alkenes Cis vs Trans Alkene Stability Zaitsev Rule Dehydrohalogenation Dehydration Reaction Infrared Spectroscopy Infrared Spectroscopy Table IR Spect: Drawing Spectra IR Spect: Extra Practice Mass Spectrometry Mass Spect: Fragmentation Mass Spect: Isotopes

Ch.12 - Reactions of Alkenes

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

Ch.13 - Alkynes

Alkynide Alkylation Dehydrohalogenation Double Elimination Hydrogenation of Alkynes Acetylide Alkynide Synthesis Alkyne Hydration Alkyne Hydroboration Alkyne Hydrohalogenation Retrosynthesis Cross-Coupling General Reactions Heck Reaction Stille Reaction Suzuki Reaction Sonogashira Coupling Reaction

Ch. 14 - Delocalized Pi 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 Electrocyclic Reactions Photochemical Electrocyclic Reactions Cumulative Electrocyclic Problems

Ch. 15 - Benzene and Aromaticty

Aromaticity Naming Benzene Rings Huckel's Rule Pi Electrons Aromatic Hydrocarbons Annulene Aromatic Heterocycles Acidity of Aromatic Hydrocarbons Basicity of Aromatic Heterocycles Ionization of Aromatics Frost Circle 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

Ch. 16 - Electrophilic Attack on Derivatives of Benzene

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 EAS: Sequence Groups EAS: Retrosynthesis

Ch. 17 - Aldehydes and Ketones

Naming Aldehydes Naming Ketones Oxidizing and Reducing Agents Oxidation of Alcohols Alkyne Hydration Ozonolysis Reducing Agent DIBAL 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 Baeyer-Villiger Oxidation Ketone and Aldehyde Synthesis Reactions

Ch. 18 - Enols, Enolates, and the Aldol Condensation

Tautomerization Tautomers of Dicarbonyl Compounds Enolate Acid-Catalyzed Alpha-Halogentation Base-Catalyzed Alpha-Halogentation Haloform Reaction Overview of Alpha-Alkylations and Acylations Enolate Alkylation and Acylation Enamine Alkylation and Acylation Condensation Reactions Aldol Condensation Directed Condensations Crossed Aldol Condensation Claisen-Schmidt Condensation Conjugate Addition Michael Addition Robinson Annulation

Ch. 19 - Carboxylic Acids

Naming Carboxylic Acids Carboxylic Acid Derivatives Diacid Nomenclature Carboxylation Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Fischer Esterification (Simplified) Hell-Volhard-Zelinski Reaction

Ch. 20 - Carboxylic Acid Derivatives

Acid Chloride Nomenclature Naming Anhydrides Naming Esters Naming Amides Naming Nitriles Nucleophilic Acyl Substitution Fischer Esterification Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Lactones, Lactams and Cyclization Reactions Nitrile to Ketone DIBAL Decarboxylation Mechanism

Ch. 21 - Amines and Their Derivatives

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

Ch. 22- Chemistry of Benzene Substituents

Side-Chain Halogenation Side-Chain Oxidation Claisen Rearrangement Cope Rearrangement Diazo Replacement Reactions Diazo Sequence Groups Diazo Retrosynthesis Phenol Acidity Nucleophilic Aromatic Substitution Benzyne

Ch. 23- Ester Enolates and the Claisen Condensation

Condensation Reactions Claisen Condensation Intramolecular Aldol Condensation Beta-Dicarbonyl Synthesis Pathway Acetoacetic Ester Synthesis Malonic Ester Synthesis

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 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 - Ruff Degradation Disaccharide Polysaccharide

Ch. 26 - Amino Acids, Peptides, Proteins, and Nucleic Acids

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