Organic Chemistry: Structure and Reactivity Ege • 5th Edition • 978-0618318094

Ch. 1 - An Introduction to Structure and Bonding

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 Resonance Structures Degrees of Unsaturation Isomer Constitutional Isomers

Ch. 2 - Covalent Bonding and Chemical Reactivity

Hybridization Molecular Geometry Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond Intermolecular Forces London Dispersion Force Van Der Waals How To Determine Solubility Functional Groups Carbonyl Amine Amide

Ch. 3 - Reactions of Organic Compounds as 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 - Reaction Pathways

Nucleophilic Substitution Addition Reaction Energy Diagram Gibbs Free Energy Enthalpy Entropy Hammond Postulate

Ch. 5 - 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 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. 6 - 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 Racemic Mixture Optical Activity Enantiomeric Excess Non-Carbon Chiral Centers Achiral

Ch. 7 - Nucleophilic Substitution and Elimination Reactions

Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E1 Reaction Solvents Leaving Groups Nucleophiles and Basicity SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination Hyperconjugation Carbocation Stability Rank the following carbocations in order of decreasing stability Dehydration Reaction

Ch. 8 - Alkenes

Alkene Stability Zaitsev Rule Dehydrohalogenation Dehydration Reaction 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

Ch. 9 - Alkynes

Dehydrohalogenation Double Elimination Acetylide Hydrogenation of Alkynes Alkyne Hydrohalogenation Alkynide Synthesis

Ch. 10 - The Chemistry of Aromatic Compounds

Aromaticity Huckel's Rule Pi Electrons Aromatic Hydrocarbons Annulene Aromatic Heterocycles Frost Circle Naming Benzene Rings Acidity of Aromatic Hydrocarbons Electrophilic Aromatic Substitution Benzene Reactions 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 EAS: Synergistic and Competitive Groups

Ch. 11 - Nuclear Magnetic Resonance Spectroscopy

Purpose of Analytical Techniques NMR Spectroscopy 1H NMR: Number of Signals H NMR Table NMR Integration Carbon NMR NMR Practice

Ch. 12 - UV and Infrared Mass Spectrometry

Infrared Spectroscopy Table IR Spect: Drawing Spectra IR Spect: Extra Practice Structure Determination without Mass Spect Mass Spectrometry Mass Spect: Fragmentation Mass Spect: Isotopes

Ch. 13 - Alcohols, Diols and Ethers

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 - Alcohol Condensation Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Ether Cleavage Alcohol Protecting Groups Thiol Reactions Sulfide Oxidation Oxidizing and Reducing Agents Oxidizing Agent Reducing Agent LiAlH4

Ch. 14 - Aldehydes and Ketones. Addition Reactions at Electrophilic Carbon Atoms

Naming Aldehydes Naming Ketones Oxidizing and Reducing Agents Oxidation of Alcohols Ozonolysis DIBAL Alkyne Hydration Nucleophilic Addition Reducing Agent Cyanohydrin Preparation of Organometallics Grignard Reaction Wittig Reaction 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 Nitrile to Ketone Ketone and Aldehyde Synthesis Reactions

Ch. 15 - Carboxylic Acids and Their Derivatives

Carboxylic Acid Carboxylic Acid Derivatives Naming Carboxylic Acids 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. 16 - Structural Effects of Acidity and Basicity: Enolization

Tautomerization Tautomers of Dicarbonyl Compounds Enolate

Ch. 17 - Enols and Enolate Anions: Alkylation and Condensation

Acid-Catalyzed Alpha-Halogentation Base-Catalyzed Alpha-Halogentation Haloform 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 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. 18 - Polyenes

Diene Conjugation Chemistry Stability of Conjugated Intermediates Allylic Halogenation Conjugated Hydrohalogenation (1,2 vs 1,4 addition) Diels-Alder Reaction Diels-Alder Retrosynthesis

Ch. 19 - Free Radicals

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. 20 - The Chemistry of Amines

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

Extra: Carbohydrates

Monosaccharide Monosaccharides - D and L Isomerism Monosaccharides - Drawing Fischer Projections Monosaccharides - Common Structures Monosaccharides - Forming Cyclic Hemiacetals Monosaccharides - Cyclization Monosaccharides - Haworth Projections Mutarotation

Extra: 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