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Structure and Bonding
- Lewis Structures in Organic Chemistry
- Valency and Formal Charges in Organic Chemistry
- How to Determine the Number of Lone Pairs
- Bonding Patterns in Organic Chemistry
- sp3, sp2, and sp Hybridization in Organic Chemistry with Practice Problems
- How to Quickly Determine The sp3, sp2, and sp Hybridization
- Bond Lengths and Bond Strengths
- VSEPR Theory - Molecular and Electron Geometry of Organic Molecules
- Dipole-dipole, London Dispersion, and Hydrogen Bonding Interactions
- Dipole Moment and Molecular Polarity
- Boiling Point and Melting Point in Organic Chemistry
- Boiling Point and Melting Point Practice Problems
- Solubility of Organic Compounds
- General Chemistry Overview Quiz
Molecular Representations
- Bond-Line or Skeletal Structures
- Functional Groups in Organic Chemistry with Practice Problems
- Bond-line, Lewis, and Condensed Structures with Practice Problems
- Curved Arrows with Practice Problems
- Resonance Structures in Organic Chemistry with Practice Problems
- Rules for Drawing Resonance Structures
- Bonding Patterns in Organic Chemistry
- Major and Minor Resonance Contributor
- Significant Resonance Structures
- How to Choose the More Stable Resonance Structure
- Drawing Complex Patterns in Resonance Structures
- Localized and Delocalized Lone Pairs with Practice Problems
- Molecular Representations Quiz
Acids and Bases
- Acids and Bases - General Chemistry
- Organic Acids and Bases
- Organic acid-base mechanisms
- Acid Strength and pKa
- How to Determine the Position of Equilibrium for an Acid-Base Reaction
- Inductive and Resonance (Mesomeric) Effects
- Factors That Determine the pKa and Acid Strength
- How Resonance Affects Acidity and Basicity
- How to Choose an Acid or a Base to Protonate or Deprotonate a Given Compound
- Lewis Acids and Bases
- Basicity of Amines
- Organic Acids and Bases Practice Problems
- Organic Acids and Bases Quiz
Alkanes and Cycloalkanes
- Naming Alkanes by IUPAC Nomenclature Rules Practice Problems
- Naming Bicyclic Compounds
- Naming Bicyclic Compounds-Practice Problems
- How to Name a Compound with Multiple Functional Groups
- Primary, Secondary, and Tertiary Carbon Atoms in Organic Chemistry
- Constitutional or Structural Isomers with Practice Problems
- Degrees of Unsaturation or Index of Hydrogen Deficiency
- The Wedge and Dash Representation
- Sawhorse Projections
- Newman Projections with Practice Problems
- Staggered and Eclipsed Conformations
- Conformational Isomers of Propane
- Newman Projection and Conformational Analysis of Butane
- Newman Projection of Chair Conformation
- Gauche Conformation
- Gauche Conformation, Steric, Torsional Strain Energy Practice Problems
- Ring Strain
- Steric vs Torsional Strain
- Conformational Analysis
- Drawing the Chair Conformation of Cyclohexane
- Axial and Equatorial Positions
- Ring Flip: Drawing Both Chair Conformations with Practice Problems
- 1,3-Diaxial Interactions and A value for Cyclohexanes
- Ring-Flip: Comparing the Stability of Chair Conformations with Practice Problems
- Cis and Trans Decalin
- IUPAC Nomenclature Summary Quiz
- Alkanes and Cycloalkanes Practice Quiz
Stereochemistry
- How to Determine the R and S Configuration
- The R and S Configuration Practice Problems
- What is Nonsuperimposable in Organic Chemistry
- Chirality and Enantiomers
- Diastereomers-Introduction and Practice Problems
- Enantiomers vs Diastereomers
- Cis and Trans Isomers
- E and Z Alkene Configuration with Practice Problems
- Enantiomers vs Diastereomers
- Enantiomers, Diastereomers, the Same or Constitutional Isomers with Practice Problems
- Configurational Isomers
- Optical Activity
- Specific Rotation
- Racemic Mixtures
- Enantiomeric Excess (ee): Percentage of Enantiomers from Specific Rotation with Practice Problems
- Symmetry and Chirality. Meso Compounds
- Fischer Projections with Practice Problems
- R and S Configuration in the Fischer Projection
- R and S configuration on Newman projections
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Converting Bond-Line, Newman Projection, and Fischer Projections
- Resolution of Enantiomers: Separate Enantiomers by Converting to Diastereomers
- Stereochemistry Practice Problems
- Stereochemistry Practice Quiz
Energy Changes In Organic Chemistry
- Energy and Organic Chemistry Reactions
- Bond Lengths and Bond Strengths
- Homolytic and Heterolytic Bond Cleavage
- The Heat of Reaction from Bond Dissociation Energies
Nucleophilic Substitution Reactions
- Introduction to Alkyl Halides
- Nomenclature of Alkyl Halides
- Substitution and Elimination Reactions
- Nucleophilic Substitution Reactions – An Introduction
- All You Need to Know About the SN2 Reaction Mechanism
The SN2 Mechanism: Kinetics, Thermodynamics, Curved Arrows, and Stereochemistry with Practice Problems - The Stereochemistry of SN2 Reactions
- Stability of Carbocations
- The SN1 Nucleophilic Substitution Reaction
- Reactions of Alkyl Halides with Water
- The Stereochemistry of the SN1 Reaction Mechanism
- The SN1 Mechanism: Kinetics, Thermodynamics, Curved Arrows, and Stereochemistry with Practice Problems
- Steric Hindrance in SN2 and SN1 Reactions
- Carbocation Rearrangements in SN1 Reactions with Practice Problems
- Ring Expansion Rearrangements
- Ring Contraction Rearrangements
- When Is the Mechanism SN1 or SN2?
- Reactions of Alcohols with HCl, HBr, and HI Acids
- SOCl2 and PBr3 for Conversion of Alcohols to Alkyl Halides
- Alcohols in SN1 and SN2 Reactions
- How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
- Exceptions in SN2 and SN1 Reactions
- Nucleophilic Substitution and Elimination Practice Quiz
- Reactions Map of Alkyl Halides
Alkenes: Structure, Stability, and Nomenclature
- Alkenes: Structure and Stability
- Naming Alkenes by IUPAC Nomenclature Rules
- Cis and Trans Isomers
- E and Z Alkene Configuration with Practice Problems
Elimination Reactions
- Substitution and Elimination Reactions
- The E2 Mechanism
- E2 Elimination Practice Problems
- Zaitsev's Rule - Regioselectivity of E2 Elimination Reactions
- The Hofmann Elimination of Amines and Alkyl Fluorides
- Stereoselectivity of E2 Elimination Reactions
- Stereospecificity of E2 Elimination Reactions
- SN2 and E2 Rates of Cyclohexanes
- Elimination Reactions of Cyclohexanes with Practice Problems
- POCl3 for Dehydration of Alcohols
- The E1 Mechanism with Practice Problems
- Regioselectivity of E1 Reactions
- Stereoselectivity of E1 Reactions
- How to tell if it is E2 or E1 Mechanism
- SN1 vs E1 Reactions
- SN2 vs E2 Reactions
- Dehydration of Alcohols by E1 and E2 Elimination
- Mesylates and Tosylates as Good Leaving Groups
- Mitsunobu Reaction
- SN1 SN2 E1 E2 – How to Choose the Mechanism
- Polar Protic and Polar Aprotic Solvents
- SN1 SN2 E1 or E2 - the Largest Collection of Practice Problems
- The Hammond Postulate
- The E1cB Elimination Mechanism
- Nucleophilic Substitution and Elimination Practice Quiz
- Reactions Map of Alkyl Halides
Addition Reactions of Alkenes
- Electrophilic Addition Reactions to Alkenes
- Markovnikov’s Rule
- Markovnikov’s Rule with Practice Problems
- Addition of Water to Alkenes
- Acid-Catalyzed Hydration of Alkenes with Practice Problems
- Rearrangements in Alkene Addition Reactions
- Oxymercuration-Demercuration
- Addition of Alcohols to Alkenes
- Free-Radical Addition of HBr: Anti-Markovnikov Addition
- Hydroboration-Oxidation: The Mechanism
- Hydroboration-Oxidation of Alkenes: Regiochemistry and Stereochemistry with Practice Problems
- Halogenation of Alkenes and Halohydrin Formation
- The Regiochemistry of Alkene Addition Reactions
- The Stereochemistry of Alkene Addition Reactions
- Cis product in an anti-Addition Reaction of Alkenes
- Ozonolysis of Alkenes with Practice Problems
- Syn Dihydroxylation of Alkenes with KMnO4 and OsO4
- Anti-Dihydroxylation of Alkenes with MCPBA and Other Peroxides with Practice Problems
- Catalytic Hydrogenation
- Oxidative Cleavage of Alkenes with KMno4 and O3
- Alkene Reactions Practice Problems
- Changing the Position of a Double Bond
- Changing the Position of a Leaving Group
- Alkenes Multi-Step Synthesis Practice Problems
- Reactions of Norbornane Derivatives
- Alkene Addition Reactions Practice Quiz
- Reactions Map of Alkenes
- Introduction to Alkynes
- Naming Alkynes by IUPAC Nomenclature Rules - Practice Problems
- Preparation of Alkynes by Elimination Reactions
- Hydrohalogenation of Alkynes
- Addition of Water to Alkynes
- Acid-Catalyzed Hydration of Alkynes with Practice Problems
- Reduction of Alkynes
- Halogenation of Alkynes
- Hydroboration-Oxidation of Alkynes with Practice Problems
- Ozonolysis of Alkynes with Practice Problems
- Alkylation of Terminal Alkynes in Organic Synthesis with Practice Problems
- Reactions of Acetylide Ions
- Alkyne reactions summary practice problems
- Alkyne Synthesis Reactions Practice Problems
- Alkyne Naming and Reactions Practice Quiz
- Reactions Map of Alkynes
Nuclear Magnetic Resonance (NMR) Spectroscopy
- NMR Spectroscopy – An Easy Introduction
- NMR Chemical Shift
- NMR Chemical Shift Range and Value Table
- NMR Number of Signals and Equivalent Protons
- Homotopic, Enantiotopic, Diastereotopic, and Heterotopic
- Homotopic Enantiotopic Diastereotopic Practice Problems
- Integration in NMR Spectroscopy
- Splitting and Multiplicity (N+1 rule) in NMR Spectroscopy
- NMR Signal Splitting N+1 Rule Multiplicity Practice Problems
- 13C Carbon NMR
- DEPT NMR: Signals and Problem Solving
- NMR Spectroscopy-Carbon-Dept-IR Practice Problems
Organic Structure Determination
- NMR Spectroscopy-Carbon-Dept-IR Practice Problems
- Interpreting IR Spectra
- Infrared (IR) Spectroscopy Practice Problems
- Solving Mass Spectrometry Practice Problems
- Mass Spectrometry Practice Problems
Radical Reactions
- Free-Radical Addition of HBr: Anti-Markovnikov Addition
- Initiation, Propagation, Termination in Radical Reactions
- Selectivity in Radical Halogenation
- Stability of Radicals
- Resonance Structures of Radicals
- Stereochemistry of Radical Halogenation with Practice Problems
- Allylic Bromination by NBS with Practice Problems
- Radical Halogenation in Organic Synthesis
Reactions of Alcohols
- Nomenclature of Alcohols: Naming Alcohols based on IUPAC Rules with Practice Problems
- Preparation of Alcohols via Substitution or Addition Reactions
- Reaction of Alcohols with HCl, HBr, and HI Acids
- Mesylates and Tosylates as Good Leaving Groups
- SOCl2 and PBr3 for Conversion of Alcohols to Alkyl Halides
- Alcohols in Substitution Reactions Practice Problems
- POCl3 for Dehydration of Alcohols
- Dehydration of Alcohols by E1 and E2 Elimination
- The Oxidation States of Organic Compounds
- LiAlH4 and NaBH4 Carbonyl Reduction Mechanism
- Alcohols from Carbonyl Reductions - Practice Problems
- Grignard Reaction in Preparing Alcohols with Practice Problems
- Grignard Reaction in Organic Synthesis with Practice Problems
- Protecting Groups For Alcohols in Organic Synthesis
- Oxidation of Alcohols: PCC, PDC, CrO3, DMP, Swern, and All of That
- Diols: Nomenclature, Preparation, and Reactions
- NaIO4 Oxidative Cleavage of Diols
- The Pinacol Rearrangement
- The Williamson Ether Synthesis
- Alcohol Reactions Practice Problems
- Naming Thiols and Sulfides
- Reactions of Thiols
- Alcohols Quiz – Naming, Preparation, and Reactions
- Reactions Map of Alcohols
Organic (Orgo) 1 Synthesis Practice Problems
Ethers and Epoxides
Conjugated Systems
- Resonance and Conjugated Dienes
- Allylic Carbocations
- 1,2 and 1,4 Electrophilic Addition to Dienes
- Kinetic vs Thermodynamic Control of Electrophilic Addition to Dienes
The Diels-Alder Reaction
- Diels-Alder Reaction: Dienes and Dienophiles
- Predict the Products of the Diels-Alder Reaction with Practice Problems
- Diels-Alder Reactions of Cyclic Dienes and Dienophiles
- Endo and Exo Products of Diels-Alder Reaction with Practice Problems
- Regiochemistry of the Diels–Alder Reaction with Practice Problems
- The Retro Diels-Alder Reaction
- Diels-Alder Reaction Practice Problem
- Diels-Alder Reaction in Organic Synthesis Practice Problems
Aromatic Compounds
- Naming Aromatic Compounds
- Introduction to Aromatic Compounds
- Benzene – Aromatic Structure and Stability
Aromaticity and Huckel's Rule - The 4n+2 Rule
- Identify Aromatic, Antiaromatic, or Nonaromatic Compounds
- Frost Circle
- Annulenes
Electrophilic Aromatic Substitution
- Electrophilic Aromatic Substitution – The Mechanism
- The Halogenation of Benzene
- The Nitration of Benzene
- The Sulfonation of Benzene
- Activating and Deactivating Groups
- Friedel-Crafts Alkylation with Practice Problems
- Friedel-Crafts Acylation with Practice Problems
- The Wolff-Kishner and Clemmensen Reductions
- Vilsmeier-Haack Reaction
- The Alkylation of Benzene by Acylation-Reduction
- Ortho, Para, Meta in EAS with Practice Problems
- Ortho, Para, and Meta in Disubstituted Benzenes
- Why Are Halogens Ortho-, Para- Directors yet Deactivators?
- Is Phenyl an Ortho/Para or Meta Director?
- Limitations of Electrophilic Aromatic Substitution Reactions
- Orientation in Benzene Rings With More Than One Substituent
- Synthesis of Aromatic Compounds From Benzene
- Arenediazonium Salts in Electrophilic Aromatic Substitution
- Reactions at the Benzylic Position
- Benzylic Bromination
- Nucleophilic Aromatic Substitution
- Nucleophilic Aromatic Substitution Practice Problems
- Reactions of Phenols
- Reactions of Aniline
- Meta Substitution on Activated Aromatic Ring
- Birch Reduction
- Electrophilic Aromatic Substitution Practice Problems
- Aromatic Compounds Quiz
- Reactions Map of Aromatic Compounds
Aldehydes and Ketones
- Nomenclature of Aldehydes and Ketones
- How to Name a Compound with Multiple Functional Groups
- Preparation of Aldehydes and Ketones
- Nucleophilic Addition to Carbonyl Groups
- Reduction of Aldehydes and Ketones
- Reactions of Aldehydes and Ketones with Water
- Reactions of Aldehydes and Ketones with Alcohols: Acetals and Hemiacetals
- Acetals as Protecting Groups for Aldehydes and Ketones
- Formation and Reactions of Imines and Enamines
- Reductive Amination
- Acetal Hydrolysis Mechanism
- Imine and Enamine Hydrolysis Mechanism
- Hydrolysis of Acetals, Imines, and Enamines: Practice Problems
- Reaction of Aldehydes and Ketones with CN, Cyanohydrin Formation
- The Wittig Reaction: Examples and Mechanism
- The Wittig Reaction: Practice Problems
- Aldehydes and Ketones to Carboxylic Acids
- Reactions of Aldehydes and Ketones - Practice Problems
- Aldehydes and Ketones Reactions Practice Quiz
- Reactions Map of Aldehydes
- Reactions Map of Ketones
Carboxylic Acids and Their Derivatives: Nucleophilic Acyl Substitution
- Preparation of Carboxylic Acids
- Naming Carboxylic Acids
- Naming Nitriles
- Naming Esters
- Naming Carboxylic Acid Derivatives – Practice Problems
- The Addition-Elimination Mechanism
- Fischer Esterification
- Ester Hydrolysis by Acid and Base-Catalyzed Hydrolysis
- What is Transesterification?
- Esters' Reaction with Amines – The Aminolysis Mechanism
- Ester Reactions Summary and Practice Problems
- Preparation of Acyl (Acid) Chlorides (ROCl)
- Reactions of Acid Chlorides (ROCl) with Nucleophiles
- R2CuLi Organocuprates - Gilman Reagent
- Reaction of Acyl Chlorides with Grignard and Gilman (Organocuprate) Reagents
- Reduction of Acyl Chlorides by LiAlH4, NaBH4, and LiAl(OtBu)3H
- Reduction of Carboxylic Acids and Their Derivatives
- Preparation and Reaction Mechanism of Carboxylic Anhydrides
- Amides - Structure and Reactivity
- Naming Amides
- Amide Hydrolysis: Acid and Base-Catalyzed Mechanism
- Amide Dehydration Mechanism by SOCl2, POCl3, and P2O5
- Amide Reduction Mechanism by LiAlH4
- Reduction of Amides to Amines and Aldehydes
- Amides Preparation and Reactions Summary
- Amides from Carboxylic Acids-DCC and EDC Coupling
- The Mechanism of Nitrile Hydrolysis To Carboxylic Acid
- Nitrile Reduction Mechanism with LiAlH4 and DIBAL to Amine or Aldehyde
- The Mechanism of Grignard and Organolithium Reactions with Nitriles
- The Reactions of Nitriles
- Converting Nitriles to Amides
- Carboxylic Acids to Ketones
- Esters to Ketones
- Synthesis and Reactions of Lactones and Lactams
- Carboxylic Acids and Their Derivatives Practice Problems
- Carboxylic Acids and Their Derivatives Quiz
- Reactions Map of Carboxylic Acid Derivatives
Alpha Carbon Chemistry: Enols and Enolates
- Keto-Enol Tautomerization
- Alpha Halogenation of Enols and Enolates
- The Haloform and Iodoform Reactions
- Alpha Halogenation of Carboxylic Acids
- Alpha Halogenation of Enols and Enolates Practice Problems
- The E1cB Elimination Mechanism
- Aldol Reaction – Principles and Mechanism
- Aldol Condensation – Dehydration of Aldol Addition Product
- Intramolecular Aldol Reactions
- Aldol Addition and Condensation Reactions – Practice Problems
- Crossed Aldol And Directed Aldol Reactions
- Crossed Aldol Condensation Practice Problems
- The Cannizzaro reaction
- Alkylation of Enolates at the Alpha Position
- Enolate Alkylation Practice Problems
- Acetoacetic Ester Synthesis
- Acetoacetic Ester Enolates Practice Problems
- Malonic Ester Synthesis
- Decarboxylation
- Michael Reaction: The Conjugate Addition of Enolates
- Robinson Annulation, Shortcut, and Retrosynthesis
- Claisen Condensation
- Dieckmann Condensation – An Intramolecular Claisen Reaction
- Crossed Claisen and Claisen Variation Reactions
- Claisen Condensation Practice Problems
- Stork Enamine Synthesis
- The Reformatsky Reaction
- Mannich Reaction
- The Knoevenagel Condensation
- Enolates in Organic Synthesis - a Comprehensive Practice Problem
Amines
- Naming Amines: Systematic and Common Nomenclature
- Preparation of Amines
- The Gabriel Synthesis of Primary Amines
- Imines from Aldehydes and Ketones with Primary Amines
- Enamines from Aldehydes and Ketones with Secondary Amines
- The Hofmann Elimination of Amines and Alkyl Fluorides
- The Reaction of Amines with Nitrous Acid
- Reactions of Amines Practice Problems
- The Cope elimination
- Basicity of Amines
- Boc Protecting Group for Amines
Organic Synthesis Problems
- Organic Chemistry Multistep Synthesis Practice Problems
- Organic Synthesis Puzzles
- Acetals as Protecting Groups for Aldehydes and Ketones
- How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
- Alkene Reactions Practice Problems
- Changing the Position of a Double Bond
- Changing the Position of a Leaving Group
- Alkenes Multi-Step Synthesis Practice Problems
- Alkyne Synthesis Reactions Practice Problems
- Radical Halogenation in Organic Synthesis
- Grignard Reaction in Organic Synthesis with Practice Problems
- Ortho Para Meta in EAS with Practice Problems
- Orientation in Benzene Rings With More Than One Substituent
Carbohydrates
- Carbohydrates – Structure and Classification
- Erythro and Threo
- R and S Configuration on Fischer Projections
- D and L Sugars
- Aldoses and Ketoses: Classification and Stereochemistry
- Epimers and Anomers
- Converting Fischer, Haworth, and Chair Forms of Carbohydrates
- Mutarotation
- Glycosides
- Isomerization of Carbohydrates
- Ether and Ester Derivatives of Carbohydrates
- Oxidation of Monosaccharides
- Reduction of Monosaccharides
- Kiliani–Fischer Synthesis
- Wohl Degradation
- Carbohydrates Practice Problem Quiz