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Organic Chemistry

Introduction to Organic Chemistry

Molecular Representations and Bonding in Organic Molecules

Valence Bond Theory and Lewis Structures

Intro to Bonding

Constitutional Isomers

Molecular Representations

Constitutional (Structural) Isomers Workbook

Constitutional (Structural) Isomers Workbook [Answers]

Drawing Bond-Line (Skeletal) Structures

Bond-Line Structures Workbook

Bond-Line Structures Workbook [Answers]

Formal Charges Practice Questions

Hybridization and VSEPR Theory

Hybridization Practice Questions

VSEPR Theory and 3D Shapes Practice Questions

Sigma and Pi Bonds in Organic Molecules

Drawing Pi Orbitals in 3D

Major vs Minor Resonance Contributors

Resonance Workbook

Resonance Workbook [Answers]

Intermolecular Forces in Organic Chemistry

Nomenclature of Organic Compounds

Nomenclature of Alkanes and Cycloalkanes

Naming Complex Substituents

Bicyclic Compounds

Bicyclic Compounds [Answers]

Nomenclature of Alkenes and Cycloalkenes

Nomenclature of Alkenes and Cycloalkenes

Nomenclature of Alkynes

Nomenclature of Alcohols

Nomenclature of Aldehydes and Ketones

Nomenclature of Carboxylic Acids

Functional Groups in Organic Chemistry

Functional Groups Workbook

Functional Groups Workbook [Answers]

Identify Functional Groups

Find A Missing Functional Group

Conformations and Stereochemistry

Dashes and Wedges

Fischer Projections

Fischer Projections

Newman Projections

How to Draw Chair Conformations

Conformational Analysis

Newman Projections Practice Questions

Newman Projections [Answers]

Chair Conformations Practice Questions

Chair Conformations [Answers]

How to Identify Chiral Atoms, Chiral Molecules, and Meso Compounds

Chirality [Answers]

CIP Rules and R/S Stereodescriptors

R/S Stereodescriptors

Enantiomers and Diastereomers

Stereochemical Relationships

How to Find Stereoisomers

Stereospecific vs Stereoselective Reactions

Reactivity: Kinetics, Thermodynamics, Types of Reactions

Carbocations: Stability and Rearrangements

Carbocations GQ

How to Use Curved Arrows

What is the Difference Between a Transition State and an Intermediate?

Electrophiles and Nucleophiles

Markovnikov’s Rule

HOMO-LUMO Interactions

Oxidation States in Organic Molecules

Oxidation States

Acid-Base Chemistry

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

Ranking Acids According to Their Strength

Typical Acid-Base Exam and Homework Questions

Drawing Curved Arrows in Acid-Base Reactions Workbook

Curved Arrow in ABC Workbook [Answers]

How to Find the Most Acidic Proton in a Molecule

Lewis Acids and Bases

Substitution and Elimination Reactions

SN1 Reactions with Carbocation Rearrangements

SN1, SN2, E1, E2 Predictive Model: How to Decide Which Mechanism We Have

Axial Leaving Group Reactivity

Intro to Substitution and Elimination Reactions

Hydrohalogenation of Alkenes

Hydration of Alkenes

Stereochemistry of Hydration and Hydrohalogenation

Halogenation of Alkenes

Oxyhalogenation of Alkenes

Oxymercuration-Reduction of Alkenes

Hydroboration-Oxidation of Alkenes

Hydrogenation (Reduction) of Alkenes

The Simmon-Smith Reaction and Cyclopropanation of Alkenes

Epoxidation of Alkenes

Ozonolysis of Alkenes

Cyclopropanation of Alkenes and the Simmons-Smith Reaction

How to Convert a Trans Alkene into a Cis Alkene?

Hydrohalogenation of Alkynes

Reduction of Alkynes

Reactions of Alkynide Ions

Hydration of Alkynes

Hydroboration-Oxidation of Alkynes

Halogenation of Alkynes

Ozonolysis of Alkynes

Conjugated Systems and Pericyclic Reactions

Molecular Orbital Description of the π-Bond

Molecular Orbitals of the Conjugated Systems

Finding Conjugated Systems

Counting Electrons in a Conjugated System

Examples of MO’s in Typical Conjugated Systems

Hydrohalogenation of Dienes

Cope Rearrangement

Claisen Rearrangement

Cascading Claisen into Cope Mechanism Challenge

The Diels-Alder Reaction

How To Predict the Diels-Alder Starting Materials

Aromatic Compounds and Aromaticity

What is Aromatic?

Aromatic or Not?

Electrophilic Aromatic Substitution (Halogenation, Nitration, Sulfonation)

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

Reactions of Aromatic Compounds Workbook

Nucleophilic Aromatic Substitution

Benzyne Chemistry

Benzyne Chemistry Challenge Mechanism

Birch Reduction

Oxidation of Alcohols: Overview

Jones Oxidation

Oxidation of Alcohols with PCC

Swern Oxidation

An Unexpected Oxidation Challenge Mechanism

Dehydration of Alcohols

Pinacol Rearrangement

Pinacol Rearrangement Practice Questions

Conversions of Alcohols into Alkyl Halides

Alcohol Protecting Groups

Ethers and Epoxides

Williamson Ether Synthesis

Cleavage of Ethers with Acids

Synthesis of Epoxides

Epoxide Opening

Tricky Epoxidation Mechanism Challenge

Another Tricky Epoxidation Exam Question

Aldehydes and Ketones

Synthesis of Aldehydes and Ketones

Formation of Hydrates from Aldehydes and Ketones

Acetals Formation and Hydrolysis

Acetal Mechanism Challenge

Formation of Imines and Enamines

The Wittig Reaction

Baeyer-Villiger Oxidation

Benzoin Condensation

Reduction of Aldehydes and Ketones with Complex Hydrides

Wolff-Kishner Reduction

Corey-Chaykovsky Epoxidation

Carboxylic Acids and Carboxylic Acid Derivatives

Acidity of Carboxylic Acids

Ranking 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

Mechanism Challenge: Moving Ester

Mechanism Challenge: Epoxide Formation

Hydrolysis of Nitriles

Decarboxylation of Carboxylic Acids

Reduction of Carboxylic Acids and Derivatives with Complex Hydrides

Koch-Haaf Carbonylation

Enols and Enolates

Acidity of Carbonyls

Enolization of Carbonyls

Keto-Enol Tautomerism

Halogenation of Ketones and Haloform Reaction

Alkylation of Enolates

Alkylation of Enolates GQ 1

Alkylation of Enolates GQ 2

Malonic Ester Synthesis

Aldol Condensation

Mixed Aldol Condensation

Intramolecular Aldol Condensation

Aldol Condensation Practice Questions

Retro-Aldol Challenge Mechanism

Claisen Condensation

Dieckmann Condensation

Retro-Dieckmann Challenge Mechanism

Michael Addition

Robinson Annulation

Stobbe Condensation

Mannich Reaction

Stork Enamine Synthesis

Basicity of Amines

Staudinger Reaction

Reductive Amination

Hofmann and Curtius Rearrangements

Gabriel Synthesis

Hofmann Elimination

Cope Elimination

Organometallic Compounds

Grignard Reagent and Grignard Reaction

Grignard Reaction of Nitriles

Grignard Reaction of Epoxides

Synthesis of Alcohols Using the Grignard Reaction

Reaction of Carboxylic Acids with Organometallic Reagents

Gilman Reagent (Organocuprates)

Radical Reactions

Radical Halogenation of Alkanes

Radical Hydrohalogenation of Alkenes (Anti-Markovnikov Addition of HBr to Alkenes)

Nomenclature of Carbohydrates (the Fundamentals)

Converting Between Fischer, Haworth, and Chair Forms of Carbohydrates

Organic Chemistry Review (T/F)

Chirality [Answers]

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