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Organic Chemistry
Acknowledgements
Lessons
Virtual Textbook of Organic Chemsitry
Explore the Molecules in 3D with MINI
Atomic Orbitals
s - Orbitals
2p - Orbitals
3p - Orbitals
3d - Orbitals
4f - Orbitals
Comparison between s and p Orbitals
Molecular Orbitals
Hydrogen
Ethylene
Acetylene
Methane
Butadiene
Benzene
Aromaticity and molecular Orbitals
Conjugation
Butadiene vs Ethylene Comparison
Linear Polyenes
Introduction to the Color in Organic Molecules
Synthesis of an Azo Dye
Stereochemistry
Introduction to the Stereochemistry
Conformations
Example of Conformations
Conformations of Ethane
Conformations of Butane
Eclipsed and Staggered Conformations of Butane
Conformational Analysis of Butane
Interactive Conformational Analysis of Butane
Conformations of Cyclohexane
Structure and Conformation of Decalin
Cis-Trans Inversion of Decalin
Chirality
Enantiomers - Mirror Images
Enantiomers - R and S Configurations
Example 1
Example 2
Example 3
Chiral or Achiral
Achiral Cyanohydrin
Achiral Cyanohydrin - 2
Chiral Cyanohydrins
Molecules with a Symmetry Plan
Diastereoisomers
Meso Forms
Exercises
Drawing Molecules in 2D and 3D
Visualizing Molecules
Conformational Analysis: Butane
Chirality? Hands-On! A Step-by-Step Guide
Determination of E/Z Isomers : A Step-by-Step Guide
Nomenclature
Nomenclature Rules
Structure → Name Nomenclature
Name Your Molecule (IUPAC)
Stereochemistry
Enantiomers
Configurational Isomers
Exercises... Somewhere on the Web
Exercises at MSU
NMR
1H Spectrum Simulation
13C Spectrum Simulation
1H-1H COSY Spectrum Simulation
1H-13C HMBC Spectrum Simulation
Mechanisms
Alkanes
Chlorination of Alkanes
Alkenes
Electrophilic Addition Reaction to Alkenes
Addition of Bromine to Alkenes
Addition of Bromine to Ethylene
Stereospecific Addition
Addition of HBr
Addition of HBr to a Symmetric Alkene
Addition of HBr to an Unsymmetrical Alkene
Regioselective Addition
Epoxidation Reactions
Hydroboration of Alkenes
Reactions of Carbenes with Alkenes
Carbene Formation
Reactions of Carbenes
Reazione di Simmons - Smith
Cleavage of 1,2-diols with Periodate
Alkyl Halides
Nucleophilic Substitution Reactions
SN2 Nucleophilic Substitution
Comparing SN1 vs SN2
Carbocation Structure and Stability
SN2 Reactions
Elimination Reactions
E1 Mechanism
E1 Reaction
Reazione E1cb
E2 Mechanism
E2 Reaction
Stereoselectivity of the E2 Reaction
Stereospecificity of the E2 reaction
E2 Elimination Regioselectivity - A
E2 Elimination Regioselectivity - B
Aromatic Compounds
Electrophilic Aromatic Substitution
Nitration of Benzene
Sulfonation of Benzene
Friedel - Crafts Alkylation
Friedel - Crafts Acylation
Nucleophilic Aromatic Substitution
Elimination - Addition: Benzyne
Addition - Elimination: Activated Nucleophilic Aromatic Substitution
Dienes
Bromination of Dienes: Addition 1,4
Diels - Alder Reaction
Introduction to the Diels - Alder reaction
Identifying Products in the Diels - Alder reaction
Regioselectivity of the Diels - Alder Reaction
Explanation of the Regioselectivty in the Diels - Alder Reaction
s-cis and s-trans Configurations
Endo vs Exo Products Formation
Alcohols
Esterification with Acyl Chlorides
Oxidation of Alcohols to Carbonyl
Esterification - Acid Catalysis
Aldehydes and Ketones
Nucleophilic Addition to the Carbonyl
Reduction with NaBH4
Addition of Organometallic Reagents - Grignard and Organolithium
Addition of Cyanide - Cyanohydrin Formation
Addition of Alcohols - Formation of Hemiacetals
Addition of Alcohols - Formation of Acetals
Addition of Amines - Formation of Imines
Addition of Amines: Formation of Enamines
Addition of Nitrogen Nucleophiles - Oximes
Addition. of Nitrogen Nucleophiles - Hydrazones
Ylides: Wittig Reaction
Reduction to Alkanes - Wolgf-Kishner Reaction
Conjugate Addition to the Carbonyl
Influence of Conjugation on the Reactivity of Carbonyl
Enolization
Direct Addition to Enol
Conjugate Addition - Examples
Conjugate Addition of Enolates
Robinson Annulation
Enolates and Enols
Aldol Condensation -Basic Catalysis (Lithium Enolates)
Aldol Condensation - Acid Catalysis
Intramolecular Aldol Condensation
Alkylation of Enolates - Claisen Condensation
Knoevenagel Condensation
Bromination of Ketones - Acid Catalysis
Bromination of Ketones - Basic Catalysis
Carboxylic Acids and Derivatives
Esterification - Acid Catalysis
Formation of Acyl Chlorides
Formation of Amides
Pericyclic Reactions
Introduction to Pericyclic Reactions
Cycloaddition Reactions
Diels -Alder Reaction
Formation of 1,2,3-Triazoles - Click Chemistry
Sigmatropic Reactions
Sigmatropic Transposition [1,5]
Sigmatropic Transposition [1,7]
Claisen Transposition - Aromatic
Claisen Transposition - Acyclic
Electrocyclic Reactions
Stereospecifity of Electrocyclic Reactions
Conrotatory Mechanism - Cyclobutene
Disrotatory Mechanism - Hexatriene
Resources
Virtual textbook of organic chemistry - MSU
Exercises of nomenclature "Trivial Names" - Uni-Wien
Exercises of nomenclature - Nomenclature 101 - Univ-Ottawa
OPSIN: Open Parser for Systematic IUPAC nomenclature - Univ-Cambridge
Synthesis exercises (Beginner) - Uni-Wien
Exercises of Nomenclature and Reactivity - UCD Dublin
Chemagic - Illinois State University
Exercises of Stereochemistry (Prof. Bays - Notre Dame Univ, USA)
Chemistry in JSMol (G. Striccoli, in Italian)
ReactionZoo (Prof. Muzika - Centre College, Kentucky - USA)
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Video Tutorial
Videotutorial 1: Drawing Molecules in 2D and 3D
Videotutorial: 2. Assigning Chirality - A Step-by-Step Guide
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