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Organic Chemistry Organic Chemistry
Organic Chemistry

Organic Chemistry Smith • 2nd Edition • 978-0073327495

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

Lewis Structure Condensed Structural Formula Degrees of Unsaturation Constitutional Isomers Resonance Structures Hybridization Molecular Geometry Electronegativity

Ch. 2 and 3 - Functional Groups, and Acids and Bases

Intermolecular Forces How To Determine Solubility Functional Groups Reaction Mechanism Acids and Bases Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity

Ch. 4 - Alkanes

IUPAC Naming Alkyl Groups Naming Cycloalkanes Naming Bicyclic Compounds Naming Alkyl Halides Naming Alkenes Naming Alcohols Cis vs Trans 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 Decalin Oxidizing and Reducing Agents

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 Optical Activity Enantiomeric Excess Calculations with Enantiomeric Percentages

Ch. 6 - Understanding Organic Reactions

Organic Chemistry Reactions Reaction Mechanism Energy Diagram Gibbs Free Energy Enthalpy Entropy

Ch. 7 - Alkyl Halides and Nucleophilic Substitution

Nucleophilic Substitution Good Leaving Groups SN2 Reaction SN1 Reaction Carbocation Stability Carbocation Intermediate Rearrangements Hammond Postulate Substitution Comparison

Ch. 8 - Alkyl Halides and Elimination Reactions

E2 Mechanism 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 Alkene Stability Zaitsev Rule Dehydrohalogenation Double Elimination

Ch. 9 - Alcohols, Ethers and Epoxides

Alcohol Nomenclature Naming Ethers Naming Epoxides Dehydration Reaction POCl3 Dehydration Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Alcohol Synthesis Williamson Ether Synthesis Making Ethers - Acid-Catalyzed Alkoxylation Making Ethers - Cumulative Practice Ether Cleavage Thiol Reactions Sulfide Oxidation Epoxidation Epoxide Reactions

Ch. 10 - Alkenes

Addition Reaction Markovnikov Hydrohalogenation Acid-Catalyzed Hydration Oxymercuration Hydroboration Halogenation Halohydrin

Ch. 11 - Alkynes

Double Elimination Alkyne Hydrohalogenation Alkyne Halogenation Alkyne Hydration Alkyne Hydroboration Acetylide Alkynide Synthesis Synthetic Cheatsheet Moving Functionality Alkynide Alkylation Alkane Halogenation Retrosynthesis

Ch. 12 - Oxidation and Reduction

Oxidizing and Reducing Agents Oxidizing Agent Reducing Agent Hydrogenation Hydrogenation of Alkynes Ozonolysis Ozonolysis Full Mechanism Oxidative Cleavage Alkyne Oxidative Cleavage Epoxidation Dihydroxylation Sharpless Epoxidation

Ch. 13 - Mass Spect and Infrared 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

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 - Radical Reactions

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

Ch. 16 - Conjugation, Resonance and Dienes

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

Ch. 17 - Benzene and Aromatic Compounds

Aromaticity Huckel's Rule Pi Electrons Aromatic Hydrocarbons Annulene Aromatic Heterocycles Molecular Orbital Theory Drawing Atomic Orbitals Drawing Molecular Orbitals HOMO LUMO Frost Circle Naming Benzene Rings Acidity of Aromatic Hydrocarbons Basicity of Aromatic Heterocycles Ionization of Aromatics

Ch. 18 - Reactions of Aromatic Compounds: Electrophilic Aromatic Substitution

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 EAS: Synergistic and Competitive Groups Side-Chain Halogenation Side-Chain Oxidation EAS: Sequence Groups EAS: Retrosynthesis

Ch. 19 - Carboxylic Acids and the Acidity of the OH Bond

Naming Carboxylic Acids Diacid Nomenclature Phenol Acidity Oxidation of Alcohols

Ch. 20 - Organometallic Reagents; Oxidation and Reduction

Oxidizing and Reducing Agents Oxidizing Agent Reducing Agent DIBAL Nucleophilic Addition Alcohol Protecting Groups t-Butyl Ether Protecting Groups Silyl Ether Protecting Groups Preparation of Organometallics Grignard Reaction Organometallics on Ketones Acid Chloride to Ketone Protecting Alcohols from Organometallics Organometallic Cumulative Practice Carboxylation

Ch. 21 - Aldehydes and Ketones - Nucleophilic Addition

Naming Aldehydes Naming Ketones Alkyne Hydration Nucleophilic Addition Cyanohydrin Wittig Reaction Overview of Nucleophilic Addition of Solvents Hydrates Hemiacetal Acetal Acetal Protecting Group Thioacetal Imine vs Enamine Addition of Amine Derivatives Ketone and Aldehyde Synthesis Reactions

Ch. 22 - Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

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

Ch. 23 - Substitution Reactions of Carbonyl Alpha-Carbons

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

Ch. 24 - Carbonyl Condensation Reactions

Condensation Reactions Aldol Condensation Directed Condensations Crossed Aldol Condensation Claisen-Schmidt Condensation Claisen Condensation Intramolecular Aldol Condensation Conjugate Addition Michael Addition Robinson Annulation

Ch. 25 - Amines

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

Ch. 26 - Carbon-Carbon Bond-Forming Reactions

Cross-Coupling General Reactions Heck Reaction Stille Reaction Suzuki Reaction Carbene

Ch. 27 - Carbohydrates

Monosaccharide Monosaccharides - D and L Isomerism Monosaccharides - Drawing Fischer Projections Monosaccharides - Common Structures Monosaccharides - Forming Cyclic Hemiacetals Monosaccharides - Cyclization Monosaccharides - Haworth Projections Mutarotation Monosaccharides - Alkylation Monosaccharides - Acylation Glycoside Monosaccharides - N-Glycosides Monosaccharides - Reduction (Alditols) Monosaccharides - Weak Oxidation (Aldonic Acid) Reducing Sugars Monosaccharides - Strong Oxidation (Aldaric Acid) Monosaccharides - Kiliani-Fischer Monosaccharides - Wohl Degradation Disaccharide Polysaccharide

Ch. 28 - Amino Acids and Proteins

Proteins and Amino Acids L and D Amino Acids Polar Amino Acids Amino Acid Chart Acid-Base Properties of Amino Acids Isoelectric Point

Appendix B

Naming Bicyclic Compounds

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