Organic Chemistry Organic Chemistry
Organic Chemistry

Organic Chemistry Loudon • 6th Edition • 978-1936221349

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Ch. 1 - Chemical Bonding and Chemical 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 Resonance Structures Hybridization Molecular Geometry Electronegativity Polar Vs. Nonpolar Covalent Bond Polar Bond

Ch. 2 - Alkanes

Degrees of Unsaturation Isomer Constitutional Isomers London Dispersion Force Van Der Waals Functional Groups Carbonyl Amine Amide IUPAC Naming Alkyl Groups Alkyl t-Butyl, sec-Butyl, isobutyl, n-butyl Naming Cycloalkanes Conformational Isomers Newman Projections Drawing Newman Projections Barrier To Rotation

Ch. 3 - Acids and Bases. The Curved-Arrow Notation

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. 4 - Introduction to Alkenes

Naming Alkenes Cis vs Trans Alkene Stability Hyperconjugation Carbocation Stability Carbocation Intermediate Rearrangements Rank the following carbocations in order of decreasing stability Addition Reaction Markovnikov Hydrohalogenation Energy Diagram Gibbs Free Energy Enthalpy Entropy Hammond Postulate

Ch. 5 - Addition Reactions of Alkenes

Addition Reaction Markovnikov Acid-Catalyzed Hydration Oxymercuration Hydroboration Halogenation Halohydrin Ozonolysis Ozonolysis Full Mechanism Oxidative Cleavage Radical Reaction Radical Stability Free Radical Halogenation Radical Selectivity Anti Markovnikov Addition of Br Free Radical Polymerization Radical Synthesis

Ch. 6 - Principles of 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 Achiral Non-Carbon Chiral Centers

Ch. 7 - Cyclic Compounds: Stereochemistry of Reactions

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

Ch. 8 - Introduction to Alkyl Halides, Alcohols, Ethers, Thiols and Sulfides

Naming Alkyl Halides Naming Alcohols Alcohol Nomenclature Naming Ethers Naming Epoxides Naming Thiols Intermolecular Forces How To Determine Solubility Solvents

Ch. 9 - The Chemistry of Alkyl Halides

Alkyl Halide Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 reaction Substitution Comparison E2 Mechanism Beta Hydrogen E2 - Anti-Coplanar Requirement Zaitsev Rule Dehydrohalogenation E2 - Cumulative Practice E1 Reaction Leaving Groups Nucleophiles and Basicity SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination Preparation of Organometallics Grignard Reaction Organometallic Cumulative Practice Carbene Free Radical Halogenation Radical Selectivity

Ch. 10 The Chemistry of Alcohols and Thiols

Hydroxyl Group Dehydration Reaction Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Oxidizing and Reducing Agents Oxidizing Agent Reducing Agent LiAlH4 1H NMR: Q-Test 1H NMR: E/Z Diastereoisomerism Thiol Reactions Alcohol Synthesis

Ch. 11 - The Chemistry of Ethers, Epoxides, Glycols, and Sulfides

Williamson Ether Synthesis Making Ethers - Alcohol Condensation Making Ethers - Alkoxymercuration Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Epoxidation Epoxide Reactions Organometallic Cumulative Practice Ether Cleavage Dihydroxylation Sharpless Epoxidation Synthetic Cheatsheet Moving Functionality Alkynide Alkylation Alkane Halogenation Retrosynthesis Sulfide Oxidation

Ch. 12 - Introduction to Spectroscopy: Infrared Spectroscopy and Mass Spectrometry

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. 13 - Nuclear Magnetic Resonance Spectroscopy

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 Carbon NMR Structure Determination without Mass Spect NMR Practice

Ch. 14 - The Chemistry of Alkynes

Acetylide Alkyne Hydrohalogenation Alkyne Hydration Alkyne Hydroboration Hydrogenation of Alkynes Alkynide Synthesis

Ch. 15 - Dienes, Resonance, and Aromaticity

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 HOMO LUMO Aromaticity Huckel's Rule Pi Electrons Aromatic Hydrocarbons Annulene Aromatic Heterocycles Acidity of Aromatic Hydrocarbons Frost Circle

Ch. 16 - The Chemistry of Benzene and its Derivatives

Naming Benzene Rings 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 EAS: Synergistic and Competitive Groups EAS: Sequence Groups EAS: Retrosynthesis

Ch. 17 - Allylic and Benzylic Reactivity

Allylic Halogenation Side-Chain Halogenation Diazo Replacement Reactions Side-Chain Oxidation

Ch. 18 - The Chemistry of Aryl Halides, Vinylic Halides, and Phenols.

Nucleophilic Aromatic Substitution Phenol Acidity

Ch. 19 - The Chemistry of Aldehydes and Ketones.

Naming Aldehydes Naming Ketones Ozonolysis Alkyne Hydration Nucleophilic Addition Reducing Agent Organometallics on Ketones Protecting Alcohols from Organometallics Cyanohydrin Wittig Reaction Hydrates Hemiacetal Acetal Acetal and Hemiacetal Acetal Protecting Group Imine vs Enamine Addition of Amine Derivatives Wolff Kishner Reduction Ketone and Aldehyde Synthesis Reactions

Ch. 20 - The Chemistry of Carboxylic Acids

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

Ch. 21 - The Chemistry of Carboxylic Acid Derivatives

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

Ch. 22 - The Chemistry of Enolate Ions, Enols, and a,b- Unsaturated Carbonyl Compounds

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 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. 23 - The Chemistry of Amines

Naming Amines Amine Alkylation Gabriel Synthesis Amines by Reduction Nitrogenous Nucleophiles Reductive Amination Curtius Rearrangement Hofmann Rearrangement Hofmann Elimination Acylation of Aniline Diazo Replacement Reactions Diazo Sequence Groups Diazo Retrosynthesis

Ch. 24 - 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 - Reduction (Alditols) Monosaccharides - Weak Oxidation (Aldonic Acid) Reducing Sugars Monosaccharides - Strong Oxidation (Aldaric Acid) Monosaccharides - Oxidative Cleavage Monosaccharides - Kiliani-Fischer Monosaccharides - Ruff Degradation Disaccharide Polysaccharide

Ch. 27 - 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

Ch. 28 - Pericyclic Reactions

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