Organic Chemistry Jones • 5th Edition • 978-0393913033

Ch. 1 - Atoms and Molecues; Orbitals and Bonding

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 Resonance Structures Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond

Ch. 2 - Alkanes

Hybridization Molecular Geometry Degrees of Unsaturation Isomer Constitutional Isomers Functional Groups Carbonyl Amine Amide IUPAC Naming Alkyl Groups Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Naming Cycloalkanes Naming Alkyl Halides Conformational Isomers Newman Projections Drawing Newman Projections Barrier To Rotation Intermolecular Forces London Dispersion Force Van Der Waals Acids and Bases Give the conjugate acid for each compound below Lewis Acids and Bases

Ch. 3 - Alkenes and Alkynes

Naming Alkenes Cis vs Trans Alkene Stability Acetylide Degrees of Unsaturation Hyperconjugation Carbocation Stability Rank the following carbocations in order of decreasing stability Addition Reaction Markovnikov Hydrohalogenation Acid-Catalyzed Hydration

Ch. 4 - 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? Racemic Mixture Optical Activity Enantiomeric Excess Calculations with Enantiomeric Percentages Achiral

Ch. 5 - Rings

Naming Bicyclic Compounds Ring Strain Axial vs Equatorial Cis vs Trans Conformations Equatorial Preference Chair Flip Calculating Energy Difference Between Chair Conformations A-Values Decalin

Ch. 6 - Alkyl Halides, Alcohols, Amines, Ethers, and Their Sulfur-Containing Relatives

Naming Alkyl Halides Preparation of Organometallics Naming Alcohols Hydroxyl Group Alcohol Nomenclature Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity Solvents How To Determine Solubility Naming Amines Non-Carbon Chiral Centers Naming Ethers Naming Thiols Thiol Reactions

Ch. 7 - Substitution Reactions: The SN2 and SN1 Reactions

Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction Nucleophiles and Basicity Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary SN1 Reaction Substitution Comparison Cumulative Substitution/Elimination Dehydration Reaction Dehydrohalogenation Double Elimination Amine Alkylation Williamson Ether Synthesis Making Ethers - Cumulative Practice Ether Cleavage

Ch. 8 - Elimination Reactions: The E1 and E2 Reactions

E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Cumulative Practice E1 Reaction Leaving Groups SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination Zaitsev Rule

Ch. 9 - Analytical Chemistry: Spectroscopy

Purpose of Analytical Techniques Mass Spectrometry Mass Spect: Fragmentation Mass Spect: Isotopes 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: 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. 10 - Electrophilic Additions to Alkenes

Addition Reaction Carbocation Stability Carbocation Intermediate Rearrangements Markovnikov Hydrohalogenation Acid-Catalyzed Hydration Hydroboration Conjugation Chemistry Stability of Conjugated Intermediates Conjugated Hydrohalogenation (1,2 vs 1,4 addition)

Ch. 11 - More Additions to Pi Bonds

Hydrogenation Halogenation Halohydrin Oxymercuration Alcohol Synthesis Epoxidation Sharpless Epoxidation Epoxide Reactions Carbene Ozonolysis Ozonolysis Full Mechanism Dihydroxylation Alkyne Hydrohalogenation Alkyne Halogenation Alkyne Hydration Alkyne Hydroboration Hydrogenation of Alkynes

Ch. 12 - Radical Reactions

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

Bonus Chapter: Synthesis

Synthetic Cheatsheet Moving Functionality Alkynide Alkylation Alkane Halogenation Retrosynthesis

Ch. 13 - Dienes and the Allyl System: 2p Orbitals in Conjugation

Diene Conjugation Chemistry Stability of Conjugated Intermediates Conjugated Hydrohalogenation (1,2 vs 1,4 addition) Allylic Halogenation Diels-Alder Reaction Diels-Alder Forming Bridged Products Diels-Alder Retrosynthesis

Ch. 14 - 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 Side-Chain Halogenation Side-Chain Oxidation Birch Reduction

Ch. 15 - Substitution 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 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 Wolff Kishner Reduction EAS: Sequence Groups Diazo Replacement Reactions EAS: Retrosynthesis Diazo Sequence Groups Diazo Retrosynthesis Nucleophilic Aromatic Substitution Benzyne Phenol Acidity

Ch. 16 - Carbonyl Chemistry 1: Addition Reactions

Naming Aldehydes Naming Ketones Nucleophilic Addition Cyanohydrin Organometallics on Ketones Overview of Nucleophilic Addition of Solvents Hydrates Hemiacetal Acetal Acetal and Hemiacetal Acetal Protecting Group Silyl Ether Protecting Groups Thioacetal Imine vs Enamine Addition of Amine Derivatives Wolff Kishner Reduction Acid Chloride to Ketone Nitrile to Ketone Oxidizing Agent Reducing Agent LiAlH4 Grignard Reaction Protecting Alcohols from Organometallics Organometallic Cumulative Practice Wittig Reaction Ketone and Aldehyde Synthesis Reactions Oxidizing and Reducing Agents Oxidation of Alcohols Ozonolysis DIBAL Alkyne Hydration Sulfide Oxidation

Ch. 17 - Carboxylic Acids

Carboxylic Acid Carboxylic Acid Derivatives Naming Carboxylic Acids Diacid Nomenclature Ester Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Fischer Esterification Lactones, Lactams and Cyclization Reactions Carboxylation Decarboxylation Mechanism

Ch. 18 - Derivatives of Carboxylic Acids: Acyl Compounds

Carboxylic Acid Derivatives Naming Esters Naming Nitriles Acid Chloride Nomenclature Naming Anhydrides Naming Amides Fischer Esterification Nucleophilic Acyl Substitution Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Baeyer-Villiger Oxidation Curtius Rearrangement Hofmann Rearrangement Amines by Reduction Nitrogenous Nucleophiles Cope Elimination

Ch. 19 - Carbonyl Chemistry 2: Reactions at the Alpha Position

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 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. 20 - 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. 22 - Special Topic: Amino Acids and Polyamino Acids

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 Gabriel Synthesis

Ch. 23 - Special Topic: Reactions Controlled by Orbital Symmetry

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