Principles and Mechanisms Karty • 2nd Edition • 978-0393630749

Ch. 1: Atomic and Molecular Structure

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 Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond

Interchapter A: Nomenclature: The Basic System for Naming Simple Organic Compounds

IUPAC Naming Alkyl Groups Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Naming Cycloalkanes Naming Bicyclic Compounds Naming Alkyl Halides Naming Ethers

Ch. 2: Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties

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

Ch. 3: Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals

Hybridization Molecular Geometry

Interchapter B: Naming Alkenes, Alkynes, and Benzene Derivatives

Naming Alkenes Naming Benzene Rings

Ch. 4: Isomerism 1: Conformational and Constitutional Isomers

Degrees of Unsaturation Constitutional Isomers 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

Ch. 5: Isomerism 2: Chirality, Enantiomers, and Diastereomers

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 Monosaccharide Monosaccharides - D and L Isomerism Monosaccharides - Drawing Fischer Projections

Interchapter C: Stereochemistry in Nomenclature

Cis vs Trans

Ch. 6: The Proton Transfer Reaction: An Introduction to Mechanisms, Thermodynamics and Charge Stability

Organic Chemistry Reactions Reaction Mechanism Enthalpy Entropy Acids and Bases Give the conjugate acid for each compound below Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity Lewis Acids and Bases Energy Diagram Gibbs Free Energy

Ch. 7: An Overview of the Most Common Elementary Steps

Alkyl Halide Nucleophilic Substitution Hyperconjugation Carbocation Stability Carbocation Intermediate Rearrangements Rank the following carbocations in order of decreasing stability

Interchapter E: Naming Compounds with Functional Groups that calls for a suffix 1: Alcohols, Amines, Ketones and Aldehydes

Hydroxyl Group Naming Alcohols Naming Amines Naming Amides Naming Aldehydes Naming Ketones

Ch. 8: An Introduction to Multistep Mechanisms: SN1 and E1 Reactions

Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement E2 - Cumulative Practice E1 Reaction Solvents Leaving Groups Nucleophiles and Basicity

Ch. 9: Nucleophilic Substitution and Elimination Reactions 1

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination Hammond Postulate Alkene Stability Zaitsev Rule Dehydration Reaction Acetylide Ether Cleavage Monosaccharides - Alkylation Glycoside

Interchapter F: Naming Compounds with a Functional Group that calls for a suffix 2: Carboxylic Acids and Their Derivatives

Naming Carboxylic Acids Diacid Nomenclature Naming Esters Naming Nitriles Acid Chloride Nomenclature Intro to Organic Chemistry

Ch. 10: Nucleophilic Substitution and Elimination Reactions 2

Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Amine Alkylation Hofmann Rearrangement Williamson Ether Synthesis Making Ethers - Alkoxymercuration Making Ethers - Alcohol Condensation Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Epoxidation Epoxide Reactions Dehydrohalogenation Double Elimination Hofmann Elimination

Ch. 11: Electrophilic Addition to Nonpolar Pi-Bonds 1: Addition of a Bronsted Acid

Addition Reaction Oxidizing and Reducing Agents Markovnikov Hydrohalogenation Acid-Catalyzed Hydration Alkyne Hydrohalogenation Alkyne Hydration Diene Conjugation Chemistry Stability of Conjugated Intermediates Conjugated Hydrohalogenation (1,2 vs 1,4 addition)

Ch. 12: Electrophilic Addition to Nonpolar Pi-Bonds 2: Reactions Involving Cyclic Transition States

Oxymercuration Hydroboration Alkyne Hydroboration Halogenation Halohydrin Carbene Epoxidation Hydrogenation of Alkynes

Ch. 13: Organic Synthesis 1

Synthetic Cheatsheet Moving Functionality Alkynide Alkylation Alkynide Synthesis Alkane Halogenation Alcohol Synthesis Retrosynthesis

Ch. 14: Orbital Interactions 2: Extended Pi-Systems, Conjugation, Aromaticity

Drawing Atomic Orbitals Drawing Molecular Orbitals Orbital Diagram: 3-atoms- Allylic Ions Orbital Diagram: 4-atoms- 1,3-butadiene Aromaticity Orbital Diagram: 5-atoms- Allylic Ions Orbital Diagram: 6-atoms- 1,3,5-hexatriene Orbital Diagram: Excited States 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

Ch. 15: Structure Determination 1: UV-Vis and IR Spect

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

Ch. 16: Structure Determination 2: NMR and Mass Spect

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 Mass Spectrometry Mass Spect: Fragmentation Mass Spect: Isotopes

Ch. 17: Nucleophilic Addition to Polar Pi-Bonds 1: Addition of Strong Nucleophiles

Oxidizing and Reducing Agents Oxidizing Agent Reducing Agent LiAlH4 Nucleophilic Addition Preparation of Organometallics Grignard Reaction Organometallics on Ketones Amines by Reduction Protecting Alcohols from Organometallics Organometallic Cumulative Practice Wittig Reaction Conjugate Addition

Ch. 18: Nucleophilic Addition to Polar Pi-Bonds 2: Weak Nucleophiles

Overview of Nucleophilic Addition of Solvents Hydrates Hemiacetal Nucleophilic Addition Acetal Acetal and Hemiacetal Acetal Protecting Group Thioacetal Imine vs Enamine Addition of Amine Derivatives Cyanohydrin Wolff Kishner Reduction Tautomerization Tautomers of Dicarbonyl Compounds Enolate Condensation Reactions Aldol Condensation Directed Condensations Crossed Aldol Condensation Claisen-Schmidt Condensation Michael Addition Robinson Annulation Ketone and Aldehyde Synthesis Reactions Monosaccharides - Forming Cyclic Hemiacetals Monosaccharides - Cyclization Monosaccharides - Haworth Projections Mutarotation

Ch. 19: Organic Synthesis 2

Wolff Kishner Reduction Hydrogenation Alcohol Protecting Groups t-Butyl Ether Protecting Groups Silyl Ether Protecting Groups Oxidizing Agent Oxidation of Alcohols

Ch. 20 and 21: Nucleophilic Addition-Elimination Reactions

Carboxylic Acid Carboxylic Acid Derivatives Ester DIBAL Baeyer-Villiger Oxidation Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Fischer Esterification (Simplified) Fischer Esterification Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Lactones, Lactams and Cyclization Reactions Nitrile to Ketone Acid Chloride to Ketone Carboxylation Decarboxylation Mechanism Gabriel Synthesis 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 Claisen Condensation Intramolecular Aldol Condensation Hydrolysis

Ch. 22: Electrophilic Aromatic Substitution 1

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 Diazo Replacement Reactions Diazo Sequence Groups Diazo Retrosynthesis

Ch. 23: Electrophilic Aromatic Substitution 2

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 Side-Chain Halogenation Side-Chain Oxidation Birch Reduction EAS: Sequence Groups EAS: Retrosynthesis Nucleophilic Aromatic Substitution Benzyne

Ch. 24: The Diels-Alder Reaction and Other Pericyclic Reactions

Diels-Alder Reaction Diels-Alder Forming Bridged Products Diels-Alder Retrosynthesis Molecular Orbital Theory Dihydroxylation Ozonolysis Ozonolysis Full Mechanism Oxidative Cleavage Ozonolysis Alkyne Oxidative Cleavage HOMO LUMO Pericyclic Reaction Thermal Cycloaddition Reactions Photochemical Cycloaddition Reactions Photochemical Electrocyclic Reactions

Ch. 25: Reactions Involving Free Radicals

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

Interchapter G: Fragmentation Pathways in Mass Spectrometry

Ch. 26: Polymers

Peptide Bond Free Radical Polymerization Polysaccharide