For all the materials related to Organic Chemistry, visit:
Structure and Bonding
- Lewis Structures in Organic Chemistry
- Valency and Formal Charges in Organic Chemistry
- sp3, sp2, and sp Hybridization in Organic Chemistry with Practice Problems
- How to Quickly Determine The sp3, sp2 and sp Hybridization
- Molecular and Electron Geometry of Organic Molecules with Practice Problems
Molecular Representations
- Bond-Line or Skeletal Structures
- Functional Groups in Organic Chemistry
- Converting between Bond-line, Lewis and Condensed Structures with Practice Problems
- Curved Arrows with Practice Problems
- Resonance Structures in Organic Chemistry
- How to Choose the More Stable Resonance Structure
- Drawing Complex Patterns in Resonance Structures
- Localized and Delocalized Lone Pairs with Practice Problems
Acids and Bases
- Organic Acids and Bases
- Organic acid-base mechanisms
- Acid Strength and pKa
- How to Determine the Position of Equilibrium for an Acid–Base Reaction
- Factors That Determine the pKa and Acid Strength
- How to Choose an Acid or a Base to Protonate or Deprotonate a Given Compound
- Lewis Acids and Bases
Alkanes and Cycloalkanes
- Naming Alkanes by IUPAC nomenclature Rules Practice Problems
- Primary Secondary and Tertiary Carbon Atoms in Organic Chemistry
- Constitutional or Structural Isomers with Practice Problems
- Degrees of Unsaturation or Index of Hydrogen Deficiency
- Newman Projections with Practice Problems
- Gauche Conformation, Steric, Torsional Strain Energy Practice Problems
- Drawing the Chair Conformation of Cyclohexane
- 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
Stereochemistry
- Enantiomers Diastereomers the Same or Constitutional Isomers with Practice Problems
- Chirality and Enantiomers: Determine if Enantiomers or Identical based on R and S Configuration
- Cis and Trans Stereoisomerism in Alkenes
- E and Z Alkene Configuration with Practice Problems
- How to Determine the R and S configuration
- The R and S Configuration Practice Problems
- Determine the Relationship – Enantiomers Diastereomers or Constitutional Isomers
- Optical Activity
- Enantiomeric Excess (ee): Percentage of Enantiomers from Specific Rotation with Practice Problems
- Calculating Enantiomeric Excess from Optical Activity
- Symmetry and Chirality. Meso Compounds
- Fischer Projections with Practice Problems
- Resolution of Enantiomers: Separate Enantiomers by Converting to Diastereomers
Nucleophilic Substitution Reactions
- SN1 SN2 E1 E2 – How to Choose the Mechanism
- Is it SN1 SN2 E1 or E2 Mechanism With the Largest Collection of Practice Problems
- Introduction to Alkyl Halides
- Nomenclature of Alkyl Halides
- Introduction to Substitution Reactions
- All You Need to Know About the SN2 Reaction Mechanism
- The SN2 Mechanism: Kinetcis, Thermodynamics, Curved Arrows and Stereochemistry with Practice Problems
- Mechanism and Stereochemistry of SN2 Reactions with Practice Problems
- Mesylates and Tosylates as Good Leaving Groups
- SOCl2 and PBr3 for Conversion of Alcohols to Alkyl Halides
- The SN1 Nucleophilic Substitution Reaction
- The SN1 Mechanism: Kinetcis, Thermodynamics, Curved Arrows and Stereochemistry with Practice Problems
- The Substrate and Nucleophile in SN2 and SN1 Reactions
- The Role of the Solvent in SN1, SN2, E1 and E2 Reactions
- Carbocation Rearrangements in SN1 Reactions with Practice Problems
- When Is the Mechanism SN1 or SN2?
- How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
- Alcohols in Substitution Reactions with Tons of Practice Problems
Alkenes: Structure, Stability and Nomenclature
- Naming Alkenes by IUPAC Nomenclature Rules
- Cis and Trans Stereoisomerism in Alkenes
- E and Z Alkene Configuration with Practice Problems
Elimination Reactions
- SN1 SN2 E1 E2 – How to Choose the Mechanism
- Is it SN1 SN2 E1 or E2 Mechanism With the Largest Collection of Practice Problems
- General Features of Elimination
- The E2 Mechanism
- 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
- Elimination Reactions of Cyclohexanes with Practice Problems
- POCl3 for Dehydration of Alcohols
- The E1 Mechanism: Kinetcis, Thermodynamics, Curved Arrows and Stereochemistry with Practice Problems
- Dehydration of Alcohols by E1 and E2 Elimination
- Stereoselectivity of E1 Reactions
- Nucleophilic Substitution vs Elimination Reactions
- Regioselectivity of E1 Reactions
- E2 vs. E1 Elimination Mechanism with Practice Problems
Addition Reactions of Alkenes
- Markovnikov’s Rule with Practice Problems
- The Stereochemistry of Alkene Addition Reactions
- Free-Radical Addition of HBr: Anti-Markovnikov Addition
- Acid-Catalyzed Hydration of Alkenes with Practice Problems
- Oxymercuration-Demercuration
- Hydroboration-Oxidation: The Mechanism
- Hydroboration-Oxidation of Alkenes: Regiochemistry and Stereochemistry with Practice Problems
- Halogenation of Alkenes and Halohydrin Formation
- 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
- Oxidative Cleavage of Alkenes with KMno4 and O3
- Cis product in an anti Addition Reaction of Alkenes
- Alkene Reactions Practice Problems
- Changing the Position of a Double Bond
- Changing the Position of a Leaving Group
- Alkenes Multi-Step Synthesis Practice Problems
- Addition of Alcohols to Alkenes
Alkynes
- Introduction to Alkynes
- Naming Alkynes by IUPAC Nomenclature Rules – Practice Problems
- Preparation of Alkynes by Elimination Reactions
- Hydrohalogenation of 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
- Alkyne reactions summary practice problems
- Alkyne Synthesis Reactions Practice Problems
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
- Infrared (IR) Spectroscopy with Lots of Real Spectrum 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
- The Williamson Ether Synthesis
- POCl3 for Dehydration of AlcoholsAlcohols in Substitution Reactions with Tons of Practice Problems
- Dehydration of Alcohols by E1 and E2 Elimination
- 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 and Their Use in Organic Synthesis
- Oxidation of Alcohols: PCC, PDC, CrO3, DMP, Swern and All of That
- NaIO4 Oxidative Cleavage of Diols
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
- Endo and Exo products of Diels-Alder Reaction with Practice Problems
- Regioselectivity of the Diels–Alder Reaction with Practice Problems
- Identify the Diene and Dienophile of the Diels–Alder Reaction with Practice Problems
- 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
- Identify Aromatic, Antiaromatic, or Nonaromatic Compounds
Electrophilic Aromatic Substitution
- Electrophilic Aromatic Substitution – The Mechanism
- Friedel-Crafts Alkylation with Practice Problems
- Friedel-Crafts Acylation with Practice Problems
- The Alkylation of Benzene by Acylation-Reduction
- Ortho Para Meta Directors in Electrophilic Aromatic Substitution with Practice Problems
- Ortho Para and Meta in Disubstituted Benzenes
- Why Are Halogens Ortho-, Para- Directors yet Deactivators ?
- Limitations on Electrophilic Aromatic Substitution Reactions
- Orientation in Benzene Rings With More Than One Substituent
- Synthesis of Aromatic Compounds From Benzene
- Electrophilic Aromatic Substitution with Arenediazonium Salts
- Reactions at the Benzylic Position
- Nucleophilic Aromatic Substitution
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
- The Addition-Elimination Mechanism
- Reduction of Carbonyl Compounds by Hydride Ion
- 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
- Imines from Aldehydes and Ketones with Primary Amines
- Enamines from Aldehydes and Ketones with Secondary Amines
- Reactions of Aldehydes and Ketones with Amines-Practice Problems
- Acetal Hydrolysis Mechanism
- Imine and Enamine Hydrolysis Mechanism
- The reaction of Aldehydes and Ketones with CN Cyanohydrin Formation
- Hydrolysis of Acetals, Imines and Enamines-Practice Problems
- The Wittig Reaction: Examples and Mechanism
- The Wittig Reaction-Practice Problems
Carboxylic Acids and Their Derivatives-Nucleophilic Acyl Substitution
- Preparation of Carboxylic Acids
- 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
- Reaction of Acyl Chlorides with Grignard and Gilman (Organocuprate) Reagents
- Reduction of Acyl Chlorides by LiAlH4, NaBH4, and LiAl(OtBu)3H
- Preparation and Reaction Mechanism of Carboxylic Anhydrides
- Amides – Structure and Reactivity
- Amides Hydrolysis: Acid and Base-Catalyzed Mechanism
- Amide Dehydration Mechanism by SOCl2, POCl3, and P2O5
- Amide Reduction Mechanism by LiAlH4
- 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
- Carboxylic Acids and Their Derivatives Practice Problems
Alpha Carbon Chemistry: Enols and Enolates
- Alpha Halogenation of Enols and Enolates
- The Haloform and Iodoform Reactions
- Alpha Halogenation of Carboxylic Acids
- Alpha Halogenation of Enols and Enolates Practice Problems
- 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
- Alkylation of Enolates Alpha Position
- Enolate Alkylation Practice Problems
- Acetoacetic Ester Synthesis
- Acetoacetic Ester Enolates Practice Problems
- Malonic Ester Synthesis
- 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
- Enolates in Organic Synthesis – a Comprehensive Practice Problem
Amines
- Preparation of Amines
- The Gabriel Synthesis of Primary Amines
- The Hofmann Elimination of Amines and Alkyl Fluorides
- Imines from Aldehydes and Ketones with Primary Amines
- Enamines from Aldehydes and Ketones with Secondary Amines
- The Reaction of Amines with Nitrous Acid
- Reactions of Amines Practice Problems
Organic Synthesis Problems
- Organic Chemistry Multistep Synthesis Practice Problems
- 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 Directors in Electrophilic Aromatic Substitution 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
Quizzes for the Corresponding Chapters
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Quiz: Matter, Chemical and Physical Properties
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Nomenclature and Formulas Quiz
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Atomic Structure, Mass, and Isotopes Quiz
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Significant Figures Quiz
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Dimensional Analysis in Chemistry Quiz
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Mass, Moles, and Number of Particles Quiz
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The Stoichiometry of Chemical Reactions Quiz
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Reactions in Aqueous Solutions Quiz
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Oxidation State and Redox Reactions Quiz
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A Multiple-Choice Quiz on Gases
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Thermochemistry Quiz
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Electronic Structure of Atoms Quiz
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Periodic Table and Periodic Trends
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Chemical Bonding and Lewis Structures Quiz
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Geometry and Hybridization Quiz
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Chemical Kinetics Quiz
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Chemical Equilibrium Quiz
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Acids and Bases Quiz
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Chemical Thermodynamics Quiz
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Electrochemistry Quiz
Tags
#Alcohol Oxidation #Carbonyl reduction #Carbonyls #Diels–Alder #Electrophilic Aromatic Substitution #Grignard Reaction #Isomerism and Stereoisomerism Relationship #IUPAC Nomenclature #Markovnikov #Newman Projections #Organic Synthesis Practice Problems #Protecting Groups #Radical Halogenation #Rand S Configuration #Regioselectivity #Resonance #SN2 and SN1 mechanism #SN2 and SN1 mechanisms