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- Functional Groups in Organic Molecules
- Alkanes and Cycloalkanes
- Naming Complex Substituents
- Bicyclic Compounds
- Alkenes and Cycloalkenes
- Alkynes
- Alcohols
- Aldehydes and Ketones
- Carboxylic Acids
- Aromatic Compounds
- Amines
- Intro to Bonding and Resonance
- Sigma and Pi Bonds in Organic Molecules
- Drawing Pi Orbitals in 3D
- Hybridization and VSEPR Theory
- How to Use Curved Arrows
- Resonance in Organic Molecules
- Major vs Minor Resonance Contributors
- Resonance Workbook
- Bond Length Ranking
- Intermolecular Forces between Organic Molecules
- Hydrogen Bonding
- Bond Dissociation Energy
- Carbocations: Stability and Rearrangements
- How to Use Curved Arrows
- What is the Difference Between a Transition State and an Intermediate?
- Electrophiles and Nucleophiles
- Markovnikov’s Rule
- Oxidation States in Organic Molecules
- Allylic and Benzylic Reactivity
- How to Draw Transition States
- HOMO-LUMO Interactions
- Chemoselective vs Regioselective
- Bronsted-Lowry Acid-Base Equilibrium
- How to Estimate the pKa Values Using the pKa Table
- Ranking Acids According to Their Strength without the pKa Table
- Typical Acid-Base Exam and Homework Questions
- Drawing Curved Arrows in Acid-Base Reactions Workbook
- How to Find the Most Acidic Proton in a Molecule
- Lewis Acids and Bases
- Intro to Substitution and Elimination
- SN2 Reactions
- SN1 Reactions
- SN1 Reactions with Carbocation Rearrangements
- SN1 vs SN2 Reactions
- E1 Reactions
- SN1 vs E1 Reactions
- E2 Reactions
- E1 vs E2 Reactions
- SN2 vs E2 Reactions
- SN1, SN2, E1, E2 Predictive Model: How to Decide Which Mechanism We Have
- Polar Protic vs Polar Aprotic Solvents
- Axial Leaving Group Reactivity
- Nomenclature of Alkenes and Cycloalkenes
- Reactions of Alkenes: Overview
- Hydrohalogenation of Alkenes (Reaction with HX)
- Hydration of Alkenes (Addition of Water in Acidic Conditions)
- Stereochemistry of Hydration and Hydrohalogenation
- Halogenation of Alkenes (Reaction with Halogens)
- Oxyhalogenation of Alkenes (Reaction with X2 in H2O)
- Oxymercuration-Reduction of Alkenes
- Hydroboration-Oxidation of Alkenes
- Hydrogenation (Reduction) of Alkenes
- The Simmons-Smith Reaction and Cyclopropanation of Alkenes
- Epoxidation of Alkenes
- Ozonolysis of Alkenes
- Alkenes Workbook 1
- Nomenclature of Alkynes
- Reactions of Alkynes: Overview
- Hydrohalogenation of Alkynes (Reaction with HX)
- Reduction of Alkynes
- Reactions of Alkynide (Acetylenide) Ions
- Hydration of Alkynes (Reaction with H2O)
- Hydroboration-Oxidation of Alkynes
- Halogenation of Alkynes (Reaction with X2)
- Ozonolysis of Alkynes
- Molecular Orbital Description of the π-Bond
- Molecular Orbitals of the Conjugated Systems
- Examples of MO’s in Typical Conjugated Systems
- Hydrohalogenation of Dienes (1,2- vs 1,4-Addition)
- Cope Rearrangement
- Claisen Rearrangement
- The Diels-Alder Reaction
- How To Predict the Diels-Alder Starting Materials
- Nomenclature of Aromatic Compounds
- Reactions of Aromatic Compounds: Overview
- What is Aromatic?
- Electrophilic Aromatic Substitution (Halogenation, Nitration, Sulfonation)
- Friedel-Crafts Alkylation and Acylation Reaction
- Directing Effects in Electrophilic Aromatic Substitution Reactions
- Multiple Directing Effects and Introduction to Multistep Synthesis
- Electrophilic Aromatic Substitution in Heterocyclic Compounds
- Nucleophilic Aromatic Substitution
- Benzyne Chemistry
- Birch Reduction
- Reactions of Aromatic Compounds Workbook
- Nomenclature of Alcohols
- Structure and Properties of Alcohols
- Reactions of Alcohols: Overview
- Oxidation of Alcohols: Overview
- Jones Oxidation
- Oxidation of Alcohols with PCC
- Swern Oxidation
- Dess-Martin Periodinane and Dess-Martin Oxidation
- Dehydration of Alcohols
- Pinacol Rearrangement
- Pinacol Rearrangement Practice Questions
- Sulfonate Esters of Alcohols
- Conversions of Alcohols into Alkyl Halides
- Alcohol Protecting Groups
- Mitsunobu Reaction
- Nomenclature of Ethers and Epoxides
- Reactions of Ethers and Epoxides: Overview
- Williamson Ether Synthesis
- Cleavage of Ethers with Acids
- Synthesis of Epoxides
- Epoxide Opening
- Sharpless Epoxidation
- Nomenclature of Aldehydes and Ketones
- Reactions of Aldehydes and Ketones: Overview
- Synthesis of Aldehydes and Ketones
- Cyanohydrins
- Formation of Hydrates from Aldehydes and Ketones
- Acetals Formation and Hydrolysis
- Formation of Imines and Enamines
- Imine and Enamine Hydrolysis
- The Wittig Reaction
- Baeyer-Villiger Oxidation
- Benzoin Condensation
- Reduction of Aldehydes and Ketones with Complex Hydrides
- Clemmensen Reduction
- Wolff-Kishner Reduction
- Corey-Chaykovsky Epoxidation
- Benzilic Rearrangement
- Cannizzaro Reaction
- Beckmann Rearrangement
- Aldehydes and Ketones Workbook
- Nomenclature of Carboxylic Acids
- Reactions of Carboxylic Acids: Overview
- Acidity of Carboxylic Acids
- Synthesis of Carboxylic Acids
- Protonating A Carboxylic Acid: Which Atom To Choose?
- Fischer Esterification
- Synthesis and Reactions of Acid Chlorides
- Overview of Acyl Substitution Reactions
- Saponification of Esters
- Hydrolysis of Nitriles
- Decarboxylation of Carboxylic Acids
- Reduction of Carboxylic Acids and Derivatives with Complex Hydrides
- Partial Reduction of Acid Derivatives to Aldehydes
- Koch-Haaf Carbonylation
- Carbodiimide-Mediated Coupling
- Conversion of Amides to Nitriles
- Carboxylic Acids and Derivatives Workbook
- Reactions of Enols and Enolates: Overview
- Acidity of Carbonyls
- Enolization of Carbonyls
- Keto-Enol Tautomerism
- Halogenation of Ketones and Haloform Reaction
- Alkylation of Enolates
- Malonic Ester Synthesis
- Aldol Condensation
- Mixed Aldol Condensation
- Intramolecular Aldol Condensation
- Aldol Condensation Practice Questions
- Claisen Condensation
- Dieckmann Condensation
- Michael Addition
- Robinson Annulation
- Stobbe Condensation
- Mannich Reaction
- Stork Enamine Synthesis
- Darzens Reaction
- Favorskii Rearrangement
- Cascading Claisen into Cope Mechanism Challenge
- Benzyne Chemistry Challenge Mechanism
- An Unexpected Oxidation Challenge Mechanism
- Tricky Epoxidation Mechanism Challenge
- Another Tricky Epoxidation Exam Question
- Acetal Mechanism Challenge
- Mechanism Challenge: Moving Ester
- Mechanism Challenge: Epoxide Formation
- Retro-Aldol Challenge Mechanism
- Even Wolverine’s Claws Would Break From This Adamantane Mechanism
- Retro-Dieckmann Challenge Mechanism
- Introduction to Mass-Spectrometry
- The McLafferty Rearrangemen
- Mass Spectrometry Practice Problems
- UV-Vis Spectroscopy
- How to Read and Interpret IR Spectra
- Typical IR Exam Questions
- Introduction to NMR
- Topicity and Its Applications to NMR
- Introduction to the Splitting Patterns and Multiplicity
- Common HNMR Patterns
- HNMR Practice Questions
- HNMR Without Integrations
- Worked Syntheses Overview
Worked Syntheses
- Synthesis of a Meso Diol
- Making a Ketone from an Alkane
- Synthesis of a Bulky Alkyne
- Synthesis of Allyl Alcohol from Acetylene
- Synthesis of Dioxane from Acetylene
- Synthesis of a Complex Ester from Toluene
- Synthesis of 1,2-Dimethylcyclopentane from Methylcyclopentane
- Synthesis of Phenylacetaldehyde from Benzaldehyde
- Adding a Functional Group to the End of a Chain Problem
- Synthesis of a Complex Molecule from Simple Starting Materials
- Adding a Functional Group Next to a Carbonyl Challenge
- Synthesis of a Complex Ether
- Synthesis of a Complex Alcohol
- Synthesis of 1-Phenylacetone from Ethylbenzene
- Synthesis of 1-Methylcyclohexene from Cyclohexene
- Synthesis of an Alkene with E + Z Double Bonds
- Synthesis of Primary Amines from Carboxylic Acids
- Synthesis of an Amine from Anisole
- Synthesis of a Deuterated Naphthalene
- Synthesis of a Halogenated Alkene from Acetylene and Epoxide
- Synthesis of Hydroquinone
- Synthesis of a Substituted Ketone
- Synthesis of a Complex Aldehyde
- Synthesis of a Cyclopropane Derivative
- Synthesis of an Allylic Alcohol
- Synthesis of Cyclopropanecarboxylic Acid
- Synthesis of a Complex Ketone
- Synthesis of a Dicarbonyl
- Synthesis of Cyclopentanone from Adipic Acid
- Synthesis of a Complex Ketone from an Ester
- Synthesis of a Complex Enone from a Ketoacid
- How to Add an Ethyl Group to an Alkene
- Aromatic Synthesis Challenge
- How to Insert a Nitrogen Into a Ring
- Final Exam Style Synthesis
- Another Final Exam Synthesis
- Tricky Alcohol Synthesis
- Synthesis of a Complex Bicyclic Vinyl Halide
- Synthesis of an Ester from 2-Chlorotoluene
- Synthesis of a Complex Tri-Substituted Aromatic Compound
- Synthesis of an Oxime from an Alcohol
- Synthesis of a Complex Ether from a Simple Alkene