Organic Chemistry Brown • 8th Edition • 978-1305580350

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 - 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 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.3 - Stereoisomerism and Chirality

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.4 - Acids and Bases

Energy Diagram Gibbs Free Energy 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.5 + 6 - Alkenes and Reactions of Alkenes

Naming Alkenes Alkene Stability Hyperconjugation Carbocation Stability Carbocation Intermediate Rearrangements Rank the following carbocations in order of decreasing stability Addition Reaction Markovnikov Hydrohalogenation Acid-Catalyzed Hydration Oxymercuration Hydroboration Hydrogenation Oxidizing and Reducing Agents Halogenation Halohydrin Dihydroxylation Ozonolysis Ozonolysis Full Mechanism Oxidative Cleavage Alkyne Oxidative Cleavage

Ch.7 - Alkynes

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

Ch.8 - Haloalkanes, Halogenation and Radicals

Naming Alkyl Halides Alkyl Halide Radical Reaction Radical Stability Free Radical Halogenation Energy Diagram Gibbs Free Energy Enthalpy Entropy Radical Selectivity Hammond Postulate Calculating Radical Yields Allylic Bromination Anti Markovnikov Addition of Br Radical Synthesis

Ch.9 - Nucleophilic Substitution (Part 1)

Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison

Ch.9 - b-Elimination (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 Alkene Stability Zaitsev Rule

Ch.10 - Alcohols

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 Thiol Reactions

Ch.11 - Ethers, Epoxides and Sulfides

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

Bonus Chapter: Synthesis

Synthetic Cheatsheet Moving Functionality Alkynide Alkylation Alkane Halogenation Intro to Organic Chemistry

Ch. 12 - Infrared Spectroscopy

Purpose of Analytical Techniques Infrared Spectroscopy Infrared Spectroscopy Table IR Spect: Drawing Spectra IR Spect: Extra Practice

Ch. 13 - Nuclear Magnetic Resonance

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. 14 - Mass Spectrometry

Mass Spectrometry Mass Spect: Fragmentation Mass Spect: Isotopes

Ch. 15 - An Introduction to Organometallic Compounds

Nucleophilic Addition Preparation of Organometallics Grignard Reaction Protecting Alcohols from Organometallics Carbene Organometallic Cumulative Practice

Ch. 16 - Aldehydes and Ketones

Naming Aldehydes Naming Ketones Oxidizing and Reducing Agents Nucleophilic Addition Organometallics on Ketones Cyanohydrin 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 Oxidation of Alcohols Ozonolysis DIBAL Reductive Amination Alkyne Hydration Wolff Kishner Reduction Tautomerization Tautomers of Dicarbonyl Compounds Enolate Acid-Catalyzed Alpha-Halogentation Base-Catalyzed Alpha-Halogentation Haloform Reaction Ketone and Aldehyde Synthesis Reactions

Ch. 17 - Carboxylic Acids

Naming Carboxylic Acids Diacid Nomenclature Reducing Agent LiAlH4 Fischer Esterification (Simplified) Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Decarboxylation Mechanism

Ch. 18 - 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 Organometallics on Ketones Acid Chloride to Ketone DIBAL Carboxylation Amines by Reduction

Ch. 19 - Enolate Anions and Enamines

Condensation Reactions Aldol Condensation Crossed Aldol Condensation Claisen-Schmidt Condensation Claisen Condensation Intramolecular Aldol Condensation Overview of Alpha-Alkylations and Acylations Enolate Alkylation and Acylation Enamine Alkylation and Acylation Beta-Dicarbonyl Synthesis Pathway Acetoacetic Ester Synthesis Malonic Ester Synthesis Conjugate Addition Michael Addition Robinson Annulation Directed Condensations Hydrolysis

Ch. 20 - Dienes, Conjugated Systems, and Pericyclic Reactions

Diene Conjugation Chemistry Stability of Conjugated Intermediates 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 Photochemical Cycloaddition Reactions Sigmatropic Rearrangement Cope Rearrangement Claisen Rearrangement

Ch. 21 - Benzene and the Concept of Aromaticity

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 Phenol Acidity Side-Chain Oxidation Side-Chain Halogenation

Ch. 22- Reactions of Benzene and Its Derivatives

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 Phenol Acidity Birch Reduction

Ch. 23 - Amines

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

Ch. 24 - Catalytic Carbon-Carbon Bond Formation

Electron Configuration of Elements Coordination Complexes Ligands Electron Counting The 18 and 16 Electron Rule Cross-Coupling General Reactions Heck Reaction Stille Reaction Suzuki Reaction Sonogashira Coupling Reaction

Ch. 25 - 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. 27 - 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