Organic Chemistry Solomons • 12th Edition • 978-1118875766

Ch.1 - The Basics

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 Constitutional Isomers Resonance Structures Hybridization Molecular Geometry

Ch.2 - Families of Carbon Compounds

Electronegativity Intermolecular Forces How To Determine Solubility Functional Groups Purpose of Analytical Techniques Infrared Spectroscopy Infrared Spectroscopy Table IR Spect: Drawing Spectra IR Spect: Extra Practice

Ch.3 - An Introduction to Organic Reactions and Their Mechanisms

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

Ch.4 - Nomenclature and Conformations of Alkanes and Cycloalkanes

IUPAC Naming Alkyl Groups 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 Degrees of Unsaturation

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 - Nucleophilic Reactions Properties and Substitution Reactions of Alkyl Halides (Pt. 1)

Energy Diagram Gibbs Free Energy Enthalpy Entropy Hammond Postulate Carbocation Stability Carbocation Intermediate Rearrangements

Ch.6 - Nucleophilic Reactions Properties and Substitution Reactions of Alkyl Halides (Pt. 2)

Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison

Ch.7 - Alkenes and Alkynes I

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 Dehydrohalogenation Double Elimination Acetylide Hydrogenation of Alkynes Dehydration Reaction Alkynide Synthesis

Ch.8 - Alkenes and Alkynes II

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

Ch. 9 - Nuclear Magnetic Resonance and Mass Spect

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.10 - Radical Reactions

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

Ch.11 - Alcohols and Ethers

Alcohol Nomenclature Naming Ethers Naming Epoxides 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 - Alkoxymercuration 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 Sharpless Epoxidation

Ch.12 - Alcohols from Carbonyl Compounds

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

(Extra) Improving Your Synthetic Techniques

Synthetic Cheatsheet Moving Functionality Alkynide Alkylation Alkane Halogenation Retrosynthesis

Ch. 13- Conjugated Unsaturated 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: Excited States Pericyclic Reaction Thermal Cycloaddition Reactions Photochemical Cycloaddition Reactions

Ch. 14 - 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 15. - 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 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 Nucleophilic Aromatic Substitution Benzyne

Ch. 16 - Aldehydes and Ketones

Naming Aldehydes Naming Ketones Oxidizing and Reducing Agents Oxidation of Alcohols 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 Baeyer-Villiger Oxidation Ketone and Aldehyde Synthesis Reactions

Ch. 17 - Carboxylic Acids and Their Derivatives

Carboxylic Acid Derivatives Naming Carboxylic Acids Diacid Nomenclature 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 Ketone and Aldehyde Synthesis Reactions

Ch. 18 - Reactions at the Alpha-Carbon of Carbonyls

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. 19 - Condensation and Conjugate Addition

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

Ch. 20 - 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

Ch. 21 - Phenols

Phenol Acidity Claisen Rearrangement Cope Rearrangement

Ch. 22 - 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 - Ruff Degradation Disaccharide Polysaccharide

Ch. 23 - Lipids

Ch. 24 - Amino Acids 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