What is 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
Index of Hydrogen Deficiency (Structural)
Constitutional Isomers
Resonance Structures
Hybridization
Molecular Geometry
Electronegativity
Intermolecular Forces
Solubility
Functional Groups
Reaction Mechanism
Acid and Base Definitions
Equilibrium Constant and pKa
pKa Values
Acid Base Equilibrium
Factors Affecting Acidity
Alkane Nomenclature
Common Substituents
Cycloalkanes
Alkyl Halides
Alkenes, Alkynes and Alcohols
Cis vs Trans
Conformations
Newman Projections – Conformational Energy
Newman Projections – Method
Barrier To Rotation
Heat of Combustion
Cyclohexane – Chairs and Positions
Cyclohexane – Determination of Cis and Trans
Equatorial Preference
Chair Flip
Calculating Flip Energy
A-Values
Decalin
Intro to Redox
Types of Isomers
Chirality
Chirality Test 1 - Internal Line of Symmetry
Chirality Test 2 - Stereocenters
Cahn-Ingold-Prelog Nomenclature
Types of Stereoisomers
Meso Compounds
Chirality Test 3 - Disubstituted Cycloalkanes Shortcuts
Isometric Relationships
Fischer Projection
Fischer Configurations
Optical Activity
Enantiomeric Excess
Calculations with Enantiomeric Percentages
Overview of Chemical Reactions
Energy Diagram
Gibbs Free Energy
Enthalpy
Entropy
Introduction to Substitution
Leaving Groups
The SN2 Mechanism
The SN1 Mechanism
Carbocation Intermediates – Stability
Carbocation Intermediate – Rearrangements
Hammond Postulate
Substitution Comparison
E2 Mechanism
Recognizing Different β-Hydrogens
The Anti-Coplanar Requirement
The E1 Mechanism
Solvents
Leaving Groups
Nucleophiles and Basicity
SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
Cumulative Substitution/Elimination
Stability of Alkenes
Elimination and Zaitsev's Rule
Dehydrohalogenation
Alcohol Nomenclature
Acid-Catalyzed Dehydration
Synthesis of Alcohols Overview
General Mechanism – Addition Reaction
Markovnikov's Rule
Hydrohalogenation
Acid-Catalyzed Hydration
Oxymercuration-Reduction
Hydroboration-Oxidation
Halogenation
Halohydrin Formation
Alkyne Hydrohalogenation
Alkyne Halogenation
Alkyne Hydration
Alkyne Hydroboration
Alkynide Synthesis
Alkynide Synthesis and Retrosynthesis
Alkane Halogenation
Retrosynthesis
Intro to Redox
Catalytic Hydrogenation and Wilkinson's Catalyst
Weak Oxidative Cleavage
Oxidative Cleavage
Epoxidation
Syn Vicinal Dihydroxylation
Birch Reduction
Purpose of Analytical Techniques
Mass Spect - Introduction
Infrared Spectroscopy
1H Nuclear Magnetic Resonance - General Features
Radical Initiators
Radical Stability
Radical Chain Reaction
Radical Selectivity
Allylic Halogenation
Radical Hydrohalogenation
Radical Polymerization
Radical Synthesis
Introduction to Conjugation
Stability of Conjugated Intermediates
Allylic Halogenation
Reactions at the Allylic Position
Conjugated Hydrohalogenation
Diels-Alder Reaction - General Features
Aromaticity - Introduction
Four Tests of Aromaticity
Counting Pi Electrons
Aromaticity of Hydrocarbons
Electrophilic Aromatic Substitution – General Mechanism
Electrophilic Aromatic Substitution – Reactions
Generating Electrophiles – EAS Halogenation
Generating Electrophiles – EAS Nitration
Generating Electrophiles – Friedel-Crafts Alkylation
Generating Electrophiles – Friedel-Crafts Acylation
EAS – Monosubstituted Benzene
EAS-o, p-Major Products
Side-Chain Halogenation
Side-Chain Oxidation
Reactions at Benzylic Positions
SNAr Addition-Elimination Mechanism
Oxidation of Phenols to Quinones
Reactions of Pyrrole, Furan, and Thiophene
Directing Effects in Substituted Pyrroles, Furans, and Thiophenes
EAS Reactions of Pyridine
SNAr Reactions of Pyridine
Side-Chain Reactions of Substituted Pyridines
Nucleophilic Addition
Alcohol Protecting Groups
Preparation of Organometallics
Reactions of Organometallics
Organometallics
Use of Protecting Groups
Carbonation of Grignard Reagents
Aldehyde Nomenclature
Ketone Nomenclature
Cyanohydrins
Wittig Reaction
Hydrates
Hemiacetals
Acetals
Acetals as Protecting Groups
Thioacetals and Raney Nickel Reduction
Imines and Enamines
Addition of Ammonia Derivatives
Ketone and Aldehyde Synthesis Reactions
Carboxylic Acid Nomenclature
Diacid Nomenclature
Nitrile Nomenclature
Ketones from Nitriles
Review of Nitriles
Acid Chloride Nomenclature
Anhydride Nomenclature
Ester Nomenclature
Amide Nomenclature
COOH Derivatives and Nucleophilic Acyl Substitution
Nucleophilic Acyl Substitution – The Three Rules
Specific Carboxylic Acid Conversions
Lactones, Lactams and Cyclization Reactions
Fischer Esterification – Mechanism
Acid-Catalyzed Ester Hydrolysis – Mechanism
Base-Catalyzed Ester Hydrolysis – Mechanism
Base-Catalyzed Transesterificaation – Mechanism
Alpha Carbons and Tautomerization
Enolates
Acid-Catalyzed Alpha-Halogenation
Base-Catalyzed Alpha-Halogenation
Haloform Reaction
Hell-Volhard-Zelinski Reaction
Decarboxylation
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 Reaction
Claisen Condensation
Intramolecular Condensation
Conjugate Addition of Enones
The Michael Reaction
Robinson Annulation