Organic Chemistry Klein • 4th Edition •

Ch.1 - A Review of General Chemistry

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 Isomer Constitutional Isomers Resonance Structures Hybridization Molecular Geometry Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond

Ch.2 - Molecular Representations

Intermolecular Forces London Dispersion Force Van Der Waals How To Determine Solubility Functional Groups Carbonyl Amine Amide

Ch.3 - 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 - 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 Naming Amines 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.5 - Stereoisomerism

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 Calculations with Enantiomeric Percentages Non-Carbon Chiral Centers Achiral

Ch.6 - Chemical Reactivity and Mechanisms

Energy Diagram Gibbs Free Energy Enthalpy Entropy Hammond Postulate Hyperconjugation Reaction Mechanism Carbocation Stability Carbocation Intermediate Rearrangements Rank the following carbocations in order of decreasing stability

Ch.7 - Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison Cis vs Trans 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 Alkene Stability Zaitsev Rule Dehydrohalogenation Dehydration Reaction

Ch.8 - Addition Reactions of Alkenes

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

Ch.9 - Alkynes

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

Ch.10 - Radical Reactions

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

Ch.11 - Synthesis

Synthetic Cheatsheet Moving Functionality Alkynide Alkylation Alkane Halogenation Retrosynthesis

Ch.12 - Alcohols and Phenols

Alcohol Nomenclature Hydroxyl Group Phenol Acidity Alcohol Synthesis Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Oxidizing and Reducing Agents Reducing Agent Oxidizing Agent Ozonolysis Nucleophilic Addition Preparation of Organometallics Grignard Reaction Protecting Alcohols from Organometallics Organometallic Cumulative Practice

Ch.13 - Ethers and Epoxides; Thiols 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 Alcohol Protecting Groups t-Butyl Ether Protecting Groups Silyl Ether Protecting Groups Epoxidation Epoxide Reactions Sharpless Epoxidation Thiol Reactions Sulfide Oxidation

Ch. 14 - 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 Degrees of Unsaturation

Ch. 15 - 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 NMR Practice Carbon NMR Structure Determination without Mass Spect

Ch. 16 - Conjugated Pi Systems and Pericyclic Reactions

Diene 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 Thermal Electrocyclic Reactions Photochemical Electrocyclic Reactions Cumulative Electrocyclic Problems Photochemical Cycloaddition Reactions Sigmatropic Rearrangement Cope Rearrangement Claisen Rearrangement

Ch. 17 - Aromatic Compounds

Aromaticity Naming Benzene Rings Huckel's Rule Pi Electrons Aromatic Hydrocarbons Annulene Aromatic Heterocycles Frost Circle Acidity of Aromatic Hydrocarbons Basicity of Aromatic Heterocycles Ionization of Aromatics Side-Chain Halogenation Side-Chain Oxidation Birch Reduction

Ch. 18 - Aromatic Substitution Reactions

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 Blocking Groups - Sulfonic Acid EAS: Synergistic and Competitive Groups EAS: Sequence Groups EAS: Retrosynthesis Nucleophilic Aromatic Substitution Benzyne

Ch. 19 - Aldehydes and Ketones

Naming Aldehydes Naming Ketones Alkyne Hydration Nucleophilic Addition Cyanohydrin Organometallics on Ketones 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 Oxidation of Alcohols Ozonolysis Reducing Agent LiAlH4 DIBAL Wittig Reaction Baeyer-Villiger Oxidation Ketone and Aldehyde Synthesis Reactions

Ch. 20 - Carboxylic Acids and Their Derivatives

Carboxylic Acid Carboxylic Acid Derivatives Diacid Nomenclature Naming Carboxylic Acids Ester Naming Esters Naming Nitriles Acid Chloride Nomenclature Naming Anhydrides Naming Amides Carboxylation Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Fischer Esterification Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Nitrile to Ketone Acid Chloride to Ketone Lactones, Lactams and Cyclization Reactions

Ch. 21 - Alpha Carbon Chemistry: Enols and Enolates

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 Decarboxylation Mechanism 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. 22 - Amines

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

Ch. 23 - Introduction to Organometallic Compounds

Preparation of Organometallics Grignard Reaction Protecting Alcohols from Organometallics Organometallic Cumulative Practice Organometallics on Ketones Nitrile to Ketone Acid Chloride to Ketone Carbene

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 Epimerization Monosaccharides - Alkylation Monosaccharides - Acylation Glycoside Monosaccharides - N-Glycosides Monosaccharides - Reduction (Alditols) Monosaccharides - Weak Oxidation (Aldonic Acid) Reducing Sugars Monosaccharides - Strong Oxidation (Aldaric Acid) Monosaccharides - Kiliani-Fischer Monosaccharides - Wohl Degradation Disaccharide Polysaccharide

Ch. 25 - Amino Acids, Peptides, and 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