Organic Chemistry McMurry • 9th Edition • 978-1305080485

Ch.1 - Structure and Bonding (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 and Bonding (Part 2)

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

Ch.2 - Polar Colvalent Bonds: Acids and Bases

Electronegativity Intermolecular Forces How To Determine Solubility Resonance Structures Organic Chemistry Reactions Reaction Mechanism Acids and Bases Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity

Ch. 3 and 4 - Alkanes, Cycloalkanes and Their Stereochemistry

Functional Groups IUPAC Naming Alkyl Groups Naming Cycloalkanes Naming Alkyl Halides 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.5 - Stereochemistry at Tetrahedral Centers

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 R and S Configuration Optical Activity Enantiomeric Excess Non-Carbon Chiral Centers

Ch.6 - An Overview of Organic Synthesis

Reaction Mechanism Energy Diagram Gibbs Free Energy Enthalpy Entropy

Ch.7 - Alkenes: Structure and Reactivity

Alkene Stability Degrees of Unsaturation Naming Alkenes Cis vs Trans Carbocation Stability Carbocation Intermediate Rearrangements Hammond Postulate Addition Reaction Markovnikov Hydrohalogenation

Ch.8 - Alkenes: Reactions and Synthesis

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

Ch.9 - Alkynes: An Introduction to Organic Synthesis

Naming Alcohols Double Elimination Acetylide Hydrogenation of Alkynes Alkyne Hydrohalogenation Alkyne Halogenation Alkyne Hydration Alkyne Hydroboration Alkyne Oxidative Cleavage Oxidation of Alcohols Oxidative Cleavage Alkynide Synthesis

Ch.10 - Organohalides

Radical Reaction Radical Stability Free Radical Halogenation Radical Selectivity Calculating Radical Yields Allylic Bromination Radical Synthesis Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Nucleophilic Addition Grignard Reaction Preparation of Organometallics Oxidizing and Reducing Agents

Ch.11 - Reactions of Alkyl Halides: Nucleophilic Substitution (Part 1)

Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison

Ch.11 - Reactions of Alkyl Halides: Eliminations (Part 2)

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 Naming Alkenes Alkene Stability Zaitsev Rule

Ch. 12 - Structure Determination: Mass Spect and Infrared Spectrometry

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 - Structure Determination: 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 - Conjugated Compounds and UV Spectroscopy

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

Ch. 15 - Benzene and Aromaticity

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

Ch. 16 - Chemistry of Benzene: Electrophilic Aromatic Substitution

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 EAS: Sequence Groups EAS: Retrosynthesis EAS: Retrosynthesis Birch Reduction Nucleophilic Aromatic Substitution Benzyne Phenol Acidity

Ch. 17 - Alcohols and Phenols

Alcohol Nomenclature Oxidizing and Reducing Agents Oxidation of Alcohols Reducing Agent Nucleophilic Addition Preparation of Organometallics Grignard Reaction Protecting Alcohols from Organometallics Organometallic Cumulative Practice Dehydration Reaction POCl3 Dehydration Fischer Esterification Alcohol Protecting Groups t-Butyl Ether Protecting Groups Silyl Ether Protecting Groups

Ch. 18 - Ethers, Epoxides; Thiols, Sulfides

Naming Ethers Williamson Ether Synthesis Making Ethers - Alcohol Condensation Making Ethers - Alkoxymercuration Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Ether Cleavage Claisen Rearrangement Naming Epoxides Epoxidation Epoxide Reactions Naming Thiols Sharpless Epoxidation Thiol Reactions Sulfide Oxidation

Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition

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 Wittig Reaction Ketone and Aldehyde Synthesis Reactions Conjugate Addition

Ch. 20 - Carboxylic Acids and Nitriles

Naming Carboxylic Acids Diacid Nomenclature Naming Nitriles Carboxylation Nitrile to Ketone

Ch. 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution

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

Ch. 22 - Carbonyl Alpha-Substitution Reactions

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 Beta-Dicarbonyl Synthesis Pathway Acetoacetic Ester Synthesis Malonic Ester Synthesis

Ch. 23 - Carbonyl Condensations

Condensation Reactions Aldol Condensation Crossed Aldol Condensation Claisen-Schmidt Condensation Claisen Condensation Intramolecular Aldol Condensation Conjugate Addition Michael Addition Enamine Alkylation and Acylation Robinson Annulation

Ch. 24 - Amines and Heterocycles

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

Ch. 25 - Biomolecules: 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 - Alkylation Monosaccharides - Acylation Glycoside Monosaccharides - Reduction (Alditols) Monosaccharides - Weak Oxidation (Aldonic Acid) Reducing Sugars Monosaccharides - Strong Oxidation (Aldaric Acid) Monosaccharides - Osazones Monosaccharides - Kiliani-Fischer Monosaccharides - Wohl Degradation Disaccharide Polysaccharide

Ch. 26 - Biomolecules: 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

Ch. 30 - Orbitals and Organic Chemistry: Pericyclic Reactions

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 Thermal Cycloaddition Reactions Photochemical Cycloaddition Reactions Sigmatropic Rearrangement Cope Rearrangement Claisen Rearrangement