Organic Chemistry Organic Chemistry
Organic Chemistry

Organic Chemistry Wade (Russell) • 9th Edition • 978-0321971371

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Week 1: Functional Groups & Acid-Base Chemistry

Intro to Organic Chemistry Atomic Structure Octet Rule Bonding Preferences Formal Charges Skeletal Structure Lewis Structure Condensed Structural Formula Electronegativity Intermolecular Forces How To Determine Solubility Functional Groups Organic Chemistry Reactions Reaction Mechanism Acids and Bases Equilibrium Constant pKa Acid Base Equilibrium Ranking Acidity IUPAC Naming Alkyl Groups Naming Cycloalkanes Naming Bicyclic Compounds Naming Alkyl Halides Naming Alkenes Cis vs Trans Naming Alcohols Alcohol Nomenclature Naming Thiols Naming Ethers Naming Epoxides Naming Thiols Naming Benzene Rings Acidity of Aromatic Hydrocarbons Basicity of Aromatic Heterocycles Naming Aldehydes Naming Ketones Naming Amines Naming Carboxylic Acids Diacid Nomenclature Carboxylic Acid Derivatives Naming Esters Acid Chloride Nomenclature Naming Anhydrides Naming Nitriles Naming Amides

Week 2: Mass Spectrometry & IR Spectroscopy

Degrees of Unsaturation 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

Week 3: Molecular Structure & Stereochemistry

Wave Function Molecular Orbitals Sigma and Pi Bonds Constitutional Isomers Resonance Structures Hybridization Molecular Geometry 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 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 Non-Carbon Chiral Centers

Week 4: Kinetics & Reaction Mechanisms

Radical Reaction Radical Stability Free Radical Halogenation Energy Diagram Gibbs Free Energy Enthalpy Entropy Radical Selectivity Hammond Postulate Calculating Radical Yields Nucleophilic Substitution Good Leaving Groups Allylic Bromination SN2 Reaction SN1 Reaction Solvents Leaving Groups Nucleophiles and Basicity Carbocation Stability Carbocation Intermediate Rearrangements Substitution Comparison E2 Mechanism Beta Hydrogen E2 - Cumulative Practice E1 Reaction SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) Cumulative Substitution/Elimination

Week 5: Alkanes, Alkenes & Alkynes

Alkene Stability Zaitsev Rule Dehydrohalogenation Dehydration Reaction Radical Synthesis Addition Reaction Markovnikov Hydrohalogenation Anti Markovnikov Addition of Br Acid-Catalyzed Hydration Oxymercuration Hydroboration Hydrogenation Halogenation Halohydrin Carbene Epoxidation Epoxide Reactions Dihydroxylation Ozonolysis Ozonolysis Full Mechanism Oxidative Cleavage Alkyne Halogenation Free Radical Polymerization Dehydrohalogenation Double Elimination Acetylide Nucleophilic Addition Hydrogenation of Alkynes Alkyne Halogenation Alkyne Hydrohalogenation Alkyne Hydration Alkyne Hydroboration Alkyne Oxidative Cleavage Alkynide Synthesis

Week 7: Alcohols

Phenol Acidity Alcohol Synthesis Nucleophilic Addition Preparation of Organometallics Grignard Reaction Organometallic Cumulative Practice Oxidizing and Reducing Agents Reducing Agent Thiol Reactions Sulfide Oxidation Oxidizing and Reducing Agents Oxidation of Alcohols Leaving Group Conversions - Using HX Leaving Group Conversions - SOCl2 and PBr3 Leaving Group Conversions - Sulfonyl Chlorides Leaving Group Conversions Summary Dehydration Reaction POCl3 Dehydration Fischer Esterification