Organic Chemistry Carey • 9th Edition • 978-0073402741

Ch. 1 - Structure Determines Properties (Part 1)

Intro to Organic Chemistry Atomic Structure Octet Rule Bonding Preferences Formal Charges Skeletal Structure Lewis Structure

Ch. 1 - Structure Determines Properties (Part 2)

Condensed Structural Formula Degrees of Unsaturation Isomer Constitutional Isomers Resonance Structures Hybridization Molecular Geometry Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond Functional Groups Carbonyl Amine Amide 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. 2 - Alkanes and Cycloalkanes: Introduction to Hydrocarbons

Wave Function Molecular Orbitals Sigma and Pi Bonds IUPAC Naming Alkyl Groups Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Naming Cycloalkanes Naming Bicyclic Compounds Naming Alkyl Halides Intermolecular Forces London Dispersion Force Van Der Waals How To Determine Solubility Oxidizing and Reducing Agents

Ch. 3 - Alkanes and Cycloalkanes: Introduction to Stereochemistry

Conformational Isomers Newman Projections Drawing Newman Projections Barrier To Rotation Ring Strain Axial vs Equatorial Cis vs Trans Conformations Chair Flip Equatorial Preference Calculating Energy Difference Between Chair Conformations A-Values Calculating Energy Difference Between Chair Conformations A-Values Decalin

Ch. 4 - Alcohols and Alkyl Halides (Part.1)

Functional Groups Naming Alkyl Halides Naming Alcohols Hydroxyl Group Hammond Postulate Hyperconjugation Carbocation Stability Carbocation Intermediate Rearrangements Rank the following carbocations in order of decreasing stability Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary

Ch. 4 - Alcohols and Alkyl Halides (Part.2)

Radical Reaction Radical Stability Free Radical Halogenation Energy Diagram Gibbs Free Energy Enthalpy Entropy Radical Selectivity Calculating Radical Yields Radical Synthesis

Ch. 5 - Structure and Preparation of Alkenes: Elimination Reactions

Naming Alkenes Cis vs Trans E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Cumulative Practice E1 Reaction Alkene Stability Zaitsev Rule Dehydrohalogenation Dehydration Reaction

Ch. 6 - Addition Reactions of Alkenes

Addition Reaction Markovnikov Hydrohalogenation Anti Markovnikov Addition of Br Acid-Catalyzed Hydration Oxymercuration Hydroboration Hydrogenation Halogenation Halohydrin Epoxidation Ozonolysis Ozonolysis Full Mechanism Oxidative Cleavage Free Radical Polymerization

Ch.7 - 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 Non-Carbon Chiral Centers Achiral

Ch. 8 - Nucleophilic Substitution

Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison Solvents Leaving Groups Nucleophiles and Basicity SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination

Ch. 9 - Alkynes

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

Ch. 10 - Conjugation in Alkadienes and Allylic Systems

Diene Conjugation Chemistry Stability of Conjugated Intermediates Molecular Orbital Theory Drawing Atomic Orbitals Drawing Molecular Orbitals HOMO LUMO Orbital Diagram: 3-atoms- Allylic Ions Allylic Halogenation Orbital Diagram: 4-atoms- 1,3-butadiene Pericyclic Reaction Thermal Cycloaddition Reactions Conjugated Hydrohalogenation (1,2 vs 1,4 addition) Diels-Alder Reaction Diels-Alder Forming Bridged Products Diels-Alder Retrosynthesis

Ch. 11 - Arenes and Aromaticity

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

Ch. 12 - 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 Limitations of Friedel-Crafts Alkyation Advantages of Friedel-Crafts Acylation Wolff Kishner Reduction 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. 13 - 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 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. 14 - Organometallic Compounds

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

Ch. 15 - Alcohol, Diols, and Thiols

Alcohol Synthesis Oxidizing and Reducing Agents Reducing Agent LiAlH4 Oxidizing Agent Dihydroxylation Epoxide Reactions Fischer Esterification (Simplified) Naming Thiols Thiol Reactions

Ch. 16 - Ethers, Epoxides, and Sulfides

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

Ch. 17 - Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group

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

Ch. 18 - Carboxylic Acids

Naming Carboxylic Acids Diacid Nomenclature Carboxylation Fischer Esterification (Simplified) Decarboxylation Mechanism

Ch. 19 - Carboxylic Acids Derivatives

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

Ch. 20 - Enols and Enolates

Tautomerization Enolate Overview of Alpha-Alkylations and Acylations Enolate Alkylation and Acylation Enamine Alkylation and Acylation Tautomers of Dicarbonyl Compounds Beta-Dicarbonyl Synthesis Pathway Acetoacetic Ester Synthesis Malonic Ester Synthesis Acid-Catalyzed Alpha-Halogentation Base-Catalyzed Alpha-Halogentation Haloform Reaction Hell-Volhard-Zelinski Reaction 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. 21 - 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. 22 - Phenols

Phenol Acidity Cope Rearrangement Claisen Rearrangement

Ch. 23 - 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 - Acylation Glycoside Monosaccharides - N-Glycosides Monosaccharides - Reduction (Alditols) Monosaccharides - Weak Oxidation (Aldonic Acid) Reducing Sugars Monosaccharides - Strong Oxidation (Aldaric Acid) Monosaccharides - Oxidative Cleavage 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