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Organic Chemistry

Organic Chemistry Bruice • 6th Edition • 978-0321663139

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Ch.1 - Electronic Structure and Bonding (Part 1)

Intro to Organic Chemistry Atomic Structure Wave Function Molecular Orbitals Sigma and Pi Bonds Octet Rule Bonding Preferences Formal Charges Skeletal Structure

Ch.1 -Electronic Structure and Bonding (Part 2)

Lewis Structure Condensed Structural Formula Resonance Structures Hybridization Molecular Geometry Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond 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.2 - An Introduction to Organic Compounds

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 Bicyclic Compounds Naming Alkyl Halides Naming Alcohols Naming Ethers Naming Amines Intermolecular Forces London Dispersion Force Van Der Waals How To Determine Solubility 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 Decalin

Ch.3 - Alkenes

Degrees of Unsaturation Naming Alkenes Cis vs Trans Gibbs Free Energy Energy Diagram Enthalpy Entropy

Ch.4 - Reactions of Alkenes

Hyperconjugation Carbocation Stability Carbocation Intermediate Rearrangements Rank the following carbocations in order of decreasing stability Radical Stability Alkene Stability Addition Reaction Markovnikov Hydrohalogenation Acid-Catalyzed Hydration Oxymercuration Hydroboration Hydrogenation Halogenation Halohydrin Carbene Epoxidation Ozonolysis Ozonolysis Full Mechanism Anti Markovnikov Addition of Br Hammond Postulate

Ch.5 - 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? Fischer Projection R and S of Fischer Projections Racemic Mixture Optical Activity Enantiomeric Excess Calculations with Enantiomeric Percentages Non-Carbon Chiral Centers Achiral

Ch.6 - Reactions of Alkynes

Naming Alkenes Alkyne Hydrohalogenation Alkyne Halogenation Alkyne Hydration Alkyne Hydroboration Acetylide Alkynide Alkylation Hydrogenation of Alkynes Alkynide Synthesis

Ch.7 - Delocalized Electrons and Their Effect

Resonance Structures Diene Conjugation Chemistry Stability of Conjugated Intermediates Allylic Halogenation 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 Electrocyclic Reactions Photochemical Electrocyclic Reactions Cumulative Electrocyclic Problems Thermal Cycloaddition Reactions Photochemical Cycloaddition Reactions Sigmatropic Rearrangement Cope Rearrangement Claisen Rearrangement

Ch.8 - Substitution Reactions of Alkyl Halides

Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Substitution Comparison

Ch.9 - Elimination Reactions of Alkyl Halides

E2 Mechanism Beta Hydrogen 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 Zaitsev Rule Dehydrohalogenation Double Elimination

Ch.10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur

Hydroxyl Group Alcohol Nomenclature Naming Epoxides Naming Thiols Alcohol Synthesis Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Williamson Ether Synthesis Making Ethers - Alcohol Condensation Making Ethers - Alkoxymercuration Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Alcohol Protecting Groups Silyl Ether Protecting Groups Dehydration Reaction POCl3 Dehydration Oxidizing and Reducing Agents Oxidizing Agent Ether Cleavage Epoxidation Epoxide Reactions Thiol Reactions Sulfide Oxidation Hofmann Elimination

Ch.11 - Organometallics

Nucleophilic Addition Preparation of Organometallics Grignard Reaction Organometallic Cumulative Practice Cross-Coupling General Reactions Heck Reaction Suzuki Reaction

Ch.12 - Radicals

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

Ch. 13 - Mass Spect and Infrared Spectroscopy

Purpose of Analytical Techniques Infrared Spectroscopy Infrared Spectroscopy Table IR Spect: Drawing Spectra IR Spect: Extra Practice Mass Spectrometry Mass Spect: Fragmentation Mass Spect: Isotopes

Ch. 14 - Nuclear Magnetic Resonance

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. 15 - Aromaticity: Reactions of Benzene

Aromaticity Huckel's Rule Pi Electrons Aromatic Hydrocarbons Annulene Aromatic Heterocycles Frost Circle Acidity of Aromatic Hydrocarbons Basicity of Aromatic Heterocycles Ionization of Aromatics Naming Benzene Rings Electrophilic Aromatic Substitution Benzene Reactions EAS: Halogenation Mechanism EAS: Nitration Mechanism Blocking Groups - Sulfonic Acid EAS: Friedel-Crafts Alkylation Mechanism EAS: Friedel-Crafts Acylation Mechanism EAS: Any Carbocation Mechanism

Ch. 16 - Reactions of Substituted Benzenes

Side-Chain Halogenation Side-Chain Oxidation Naming Benzene Rings Electron Withdrawing Groups EAS: Ortho vs. Para Positions Phenol Acidity Acylation of Aniline Limitations of Friedel-Crafts Alkyation Advantages of Friedel-Crafts Acylation EAS: Synergistic and Competitive Groups EAS: Sequence Groups EAS: Retrosynthesis Diazo Replacement Reactions Diazo Sequence Groups Diazo Retrosynthesis Nucleophilic Aromatic Substitution Benzyne

Ch. 17 - Carbonyl Compounds I: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Naming Carboxylic Acids Acid Chloride Nomenclature Naming Anhydrides Ester Naming Esters Naming Amides Naming Nitriles Diacid Nomenclature Carboxylic Acid Carboxylic Acid Derivatives Fischer Esterification (Simplified) Fischer Esterification Acid-Catalyzed Ester Hydrolysis Saponification Transesterification Nucleophilic Acyl Substitution Carboxylic Acid to Acid Chloride Lactones, Lactams and Cyclization Reactions Gabriel Synthesis Carboxylation Decarboxylation Mechanism

Ch. 18 - Carbonyl Compounds II: Reactions of Aldehydes and Ketones

Naming Aldehydes Naming Ketones Oxidizing and Reducing Agents Oxidation of Alcohols DIBAL Nucleophilic Addition Cyanohydrin Organometallics on Ketones Acid Chloride to Ketone Nitrile to Ketone Overview of Nucleophilic Addition of Solvents Hydrates Hemiacetal Acetal Acetal and Hemiacetal Acetal Protecting Group Thioacetal Imine vs Enamine Addition of Amine Derivatives Wolff Kishner Reduction Reductive Amination Wittig Reaction Conjugate Addition Ketone and Aldehyde Synthesis Reactions

Ch. 19 - Carbonyl Compounds III: Reactions at the Alpha-Carbon

Tautomerization 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 Tautomers of Dicarbonyl Compounds 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 - More About Oxidation-Reduction Reactions

Oxidizing and Reducing Agents Oxidizing Agent Reducing Agent LiAlH4 Sharpless Epoxidation Baeyer-Villiger Oxidation Dihydroxylation Ozonolysis Ozonolysis Oxidative Cleavage

Ch. 21 - More About Amines

Naming Amines Amine Alkylation Amines by Reduction Nitrogenous Nucleophiles Nucleophilic Aromatic Substitution Cope Elimination

Ch. 22 - The Organic Chemistry of 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 Glycoside Monosaccharides - N-Glycosides Monosaccharides - Reduction (Alditols) Monosaccharides - Weak Oxidation (Aldonic Acid) Reducing Sugars Monosaccharides - Strong Oxidation (Aldaric Acid) Monosaccharides - Osazones Monosaccharides - Kiliani-Fischer Monosaccharides - Wohl Degradation Disaccharide Polysaccharide

Ch. 23 - The Organic Chemistry of 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

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