Introduction to Organic Chemistry Brown & Poon • 6th Edition • 9781119106968

Ch. 1 - Covalent Bonding and Shapes of Molecules

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 Isomer Resonance Structures Molecular Geometry Hybridization Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond Functional Groups

Ch. 2 - Acids and Bases

Acids and Bases Give the conjugate acid for each compound below Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity Lewis Acids and Bases

Ch. 3 - Alkanes and Cycloalkanes

IUPAC Naming Alkyl Groups Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Naming Cycloalkanes Naming Bicyclic Compounds Naming Alkyl Halides Naming Alcohols Cis vs Trans Degrees of Unsaturation Constitutional Isomers Intermolecular Forces London Dispersion Force Van Der Waals How To Determine Solubility Carbonyl Amine Amide 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. 4 - Alkenes and Alkynes

Naming Alkenes Alkene Stability Hyperconjugation Dehydrohalogenation Double Elimination Acetylide

Ch. 5 - Reactions of Alkenes and Alkynes

Organic Chemistry Reactions Reaction Mechanism Energy Diagram Gibbs Free Energy Enthalpy Entropy Carbocation Stability Carbocation Intermediate Rearrangements Addition Reaction Markovnikov Hydrohalogenation Acid-Catalyzed Hydration Oxymercuration Hydroboration Halogenation Halohydrin Dihydroxylation Ozonolysis Ozonolysis Full Mechanism Oxidative Cleavage Hydrogenation Alkyne Hydrohalogenation Alkyne Halogenation Alkyne Hydration Alkyne Hydroboration Alkyne Oxidative Cleavage Hydrogenation of Alkynes Alkynide Synthesis

Ch. 6 - Chirality: The Handedness of Molecules

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 Achiral

Ch. 7 - Haloalkanes

Naming Alkyl Halides Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Cumulative Practice E1 Reaction Zaitsev Rule Solvents Leaving Groups Nucleophiles and Basicity SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination

Ch.8 - Alcohols, Ethers, Thiols

Hydroxyl Group Alcohol Nomenclature Alcohol Synthesis Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Dehydration Reaction Oxidizing Agent Naming Ethers Williamson Ether Synthesis Making Ethers - Alcohol Condensation Making Ethers - Alkoxymercuration Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Ether Cleavage Naming Epoxides Epoxidation Epoxide Reactions Naming Thiols Thiol Reactions Sulfide Oxidation

Ch. 9 - Benzene and Its Derivatives

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 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 EAS: Synergistic and Competitive Groups Side-Chain Oxidation Side-Chain Halogenation EAS: Sequence Groups EAS: Retrosynthesis Nucleophilic Aromatic Substitution Benzyne Phenol Acidity EAS: Halogenation Mechanism

Ch. 10 - Amines

Naming Amines Amine Alkylation Diazo Replacement Reactions Diazo Sequence Groups Diazo Retrosynthesis Hofmann Elimination Cope Elimination

Ch. 11 - Spectroscopy

Purpose of Analytical Techniques Infrared Spectroscopy Infrared Spectroscopy Table IR Spect: Drawing Spectra IR Spect: Extra Practice NMR Spectroscopy 1H NMR: Number of Signals 1H NMR: Q-Test H NMR Table 1H NMR: E/Z Diastereoisomerism 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. 12 - Aldehydes and Ketones

Naming Aldehydes Naming Ketones Nucleophilic Addition Preparation of Organometallics Grignard Reaction Organometallics on Ketones Cyanohydrin Overview of Nucleophilic Addition of Solvents Hydrates Hemiacetal Acetal Acetal and Hemiacetal Acetal Protecting Group Thioacetal Imine vs Enamine Addition of Amine Derivatives Oxidizing and Reducing Agents Tautomerization Oxidation of Alcohols Ozonolysis DIBAL Reducing Agent Reductive Amination Wolff Kishner Reduction

Ch. 13 - Carboxylic Acids

Naming Carboxylic Acids Diacid Nomenclature Fischer Esterification (Simplified) Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Decarboxylation Mechanism

Ch. 14 - Functional Derivatives of Carboxylic Acids

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

Ch. 15 - Enolate Anions

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

Ch. 17 - 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 - Oxidative Cleavage Disaccharide Polysaccharide

Ch. 18 - Amino Acids 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