Virtual Textbook of Organic Chemistry

abu-omar

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http://www.cem.msu.edu/~reusch/VirtualText/intro1.htm#info

General Principles


Structure & Bonding Electron Configurations of Atoms
Chemical Bonding & Valence
Charge Distribution in Molecules
Practice Problems
The Shape of Molecules
Isomers
Analysis of Molecular Formulas
Resonance
Atomic and Molecular Orbitals
Practice Problems


Intermolecular Forces Boiling & Melting Points
Hydrogen Bonding
Crystalline Solids
Water Solubility
Practice Problems


Chemical Reactivity Reaction Classification
By Structural Change
By Reaction Type
Acid-Base Reactions
Oxidations & Reductions
By Functional Group
Reaction Variables
Reactants & Reagents
Product Selectivity
Other Variables
Reaction Rate
Intermediates
Reaction Energetics
Bond Energy
Electronic Effects
Steric Effects
Solvent Effects
Reaction Mechanisms
Curved Arrow Notation
Reactive Intermediates
Reaction Illustrations
Nucleophilicity & Basicity
Acid-Base Catalysis
Practice Problems


Aromaticity Benzene
Fused Ring Compounds
<A href="http://www.cem.msu.edu/~reusch/VirtualText/react3.htm#rx9">Other Aromatic Compounds
The Hückel Rule
Practice Problems


Nomenclature Alkanes
Cycloalkanes
Practice Problems
Alkenes & Alkynes
Substituted Benzenes
Other Functional Groups
Practice Problems


Stereoisomers Part I Alkene Configurational Isomers
Cycloalkane Configurational Isomers
Practice Problems
Conformational Isomers
Ethane
Butane
Cycloalkanes
Substituted Cyclohexanes
Practice Problems


Stereoisomers Part II Chirality & Symmetry
Symmetry Elements
Enantiomorphism
Optical Activity
Configurational Nomenclature
Compounds with Several Stereogenic Centers
Stereogenic Nitrogen
Fischer Projection Formulas
Achiral Diastereomers
Other Configurational Notations
Resolution
Conformational Enantiomorphism
Practice Problems

Summary of Isomerism


Other Topics

Spectroscopy

Mass Spectrometry
Ultraviolet-Visible Spectroscopy
Infrared Spectroscopy
Nuclear Magnetic Resonance Spectroscopy
Biochemicals

Carbohydrates
Lipids
Proteins and Amino Acids
Nucleic Acids
Free Radicals

Heterocycles

Macromolecules

Organometallic Chemistry

Pericyclic Reactions

Photochemistry

Anionic Rearrangements

Cationic Rearrangements

Introduction to Synthesis

Principles of Modern Synthesis
Stereoselective Synthesis


Functional Group Reactions


Alkanes Combustion
Substitution (of H by halogen)
Practice Problems


Alkenes Electrophilic Additions
Strong Brønsted Acids
Lewis Acids (non-Proton Electrophiles)
Electrophilic Halogen Reagents
Other Electrophilic Reagents
Reduction
Oxidation
Radical Additions
Allylic Substitution
Practice Problems
Dienes
Addition Reactions
Diels-Alder Cycloaddition
Practice Problems


Alkynes Addition Reactions
Hydrogenation
Electrophiles
Hydration & Tautomerism
Hydroboration
Nucleophilile Addition & Reduction
Acidity of Terminal Alkynes (Substitution of H)
Practice Problems


Alkyl Halides General Reactivity
Substitution(of X)
SN2 Mechanism
SN1 Mechanism
Elimination (of HX)
Summary of Substiution vs. Elimination
Substitution by Metals
Elimination Reactions of Dihalides
Practice Problems


Alcohols Nomenclature
Reactions of Alcohols
Substitution of the Hydroxyl H
Substitution of the Hydroxyl Group
Elimination of Water
Oxidation of Alcohols
Reactions of Phenols
Acidity of Phenols
Ring Substitution of Phenols
Oxidation to Quinones
Practice Problems


Ethers Nomenclature
Preparation of Ethers
Reactions of Ethers
Acid Cleavage
Peroxide Formation
Epoxide Reactions
Practice Problems


Thiols & Sulfides Sulfur Analogs of Alcohols & Ethers


Benzene & Derivatives Electrophilic Substitution
A Substitution Mechanism
Reactions of Substituted Benzenes
Reaction Characteristics
Reactions of Disubstituted Rings
Reactions of Substituent Groups
Nucleophilic Substitution, Elimination & Addition Reactions
Practice Problems


Amines Nomenclature & Structure
Properties of Amines
Boiling Point & Solubility
Basicity of Nitrogen Compounds
Acidity of Nitrogen Compounds
Important Reagent Bases
Reactions of Amines
Electrophilic Substitution at Nitrogen
Preparation of 1º-Amines
Preparation of 2º & 3º-Amines
Practice Problems
Reactions with Nitrous Acid
Reactions of Aryl Diazonium Intermediates
Elimination Reactions of Amines
Oxidation States of Nitrogen
Practice Problems


Phosphines Phosphorus Analogs of Amines


Aldehydes & Ketones Nomenclature of Aldehydes & Ketones
Occurrence of Aldehydes & Ketones
Natural Products
Synthetic Preparation
Properties of Aldehydes & Ketones
Reversible Addition Reactions
Hydration & Hemiacetal Formation
Acetal Formation
Imine Formation
Enamine Formation
Cyanohydrin Formation
Irreversible Addition Reactions
Complex Metal Hydrides
Organometallic Reagents
Carbonyl Group Modification
Wolff-Kishner Reduction
Clemmensen Reduction
Hydrogenolysis of Thioacetals
Oxidations
Reactions at the α-Carbon
Mechanism of Electrophilic α-Substitution
The Aldol Reaction
Ambident Enolate Anions
Alkylation of Enolate Anions
Practice Problems


Carboxylic Acids Nomenclature of Carboxylic Acids
Natural Products
Related Derivatives
Physical Properties
Acidity
Preparation of Carboxylic Acids
Reactions of Carboxylic Acids
Salt Formation
Substitution of Hydroxyl Hydrogen
Substitution of the Hydroxyl Group
Reduction & Oxidation
Practice Problems


Carboxylic Derivatives Physical Properties
Nomenclature
Reactions of Carboxylic Acid Derivatives
Acyl Group Substitution
Mechanism
Reduction
Catalytic Reduction
Metal Hydride Reduction
Diborane Reduction
Reaction with Organometallic Reagents
Practice Problems
Reactions at the α Carbon
Acidity of α C–H
The Claisen Condensation
Synthesis Applications
 
A-values of cyclohexyl substituents
abietic acid
absolute configuration
acetals
acetoacetic ester alkylation
acceptor reactant in the aldol reaction
achirality
achiral diastereomers
aci-anions from nitroalkanes
acid-base catalysis
acid-base equilibria
acidic and basic resolving agents
acidity constant Ka
acidity
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equilibrium acidity
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solvent effects on pKa s
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carbon acids
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α hydrogens
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stereoelectronic factors in enolization
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carboxylic acids
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kinetic acidity
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base catalyzed isotope exchange
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of nitroalkanes
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structural reorganization factor
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hybridization
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inductive effects
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resonance stabilization of carboxylate anion
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super acid
activating substituents
activation energy
activation enthalpy
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and transition state
acyl anion equivalent
acylation reactions
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specialized acylation reagents
acyl carbene rearrangements
acyl nitrene rearrangements
acyloin condensation
acyloins from thiazolium catalyzed aldehyde condensations
addition reaction defined
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addition reactions of allenes
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1,2 & 1,4-addition to dienes
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addition reaction example
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addition reactions of alkenes
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addition reactions of benzene
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addition reactions of alkynes
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addition to cyclopropane
alcohols
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nomenclature
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reactions
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dehydration
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oxidation
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substitution of hydroxyl hydrogen
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nucleophilic substitution of OH
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by hypervalent phosphorous reagents
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by way of sulfonate esters
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Williamson ether synthesis
alcoholysis
aldehydes see carbonyl compounds
the aldol reaction
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diastereoselectivity
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directed aldol reactions
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enantioselectivity
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enolborinate intermediates
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enamine aldol
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interacting substituent effects
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Mukaiyama aldol
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stereoselective synthesis
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transition state
aldoses see carbohydrates
aliphatic
alkali metals
alkaloids
alkane nomenclature
alkene configurational isomers
alkene/alkyne nomenclature
alkene reactions
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addition of Brønsted acids
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allylic substitution
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halogen additions
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hydration
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hydrogen addition
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hydroboration
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hypohalous acid additions
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Lewis acid additions
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oxidative additions
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oxymercuration
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ozonolysis
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radical additions
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radical polymerization
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stereoselectivity of addition
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hydroboration stereoselectivity
alkyl groups
alkyl halide reactions
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reaction variables
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nucleophilic substitution
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alkyl group influence
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cation effects
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molecularity
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nucleophilicity
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SN2 mechanism
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SN1 mechanism solvolysis
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solvent effects
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steric hindrance (animation)
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beta-elimination
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anti-stereospecificity
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beta-hydrogen requirement
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Bredt's rule
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E1 mechanism
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E2 mechanism
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the Zaitsev rule
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summary comparison of halide reactions
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formation of organometallic compounds
alkyl lithium reagents
alkylation of stabilized enolate anions
alkyne reactions
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acidity of terminal alkynes
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addition of nucleophiles
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hydration
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hydroboration
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hydrogen addition
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oxidation
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preparation from dihalides
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reduction by sodium in ammonia
allenes
allotropes of carbon
allyl group
allyl radical
allylic Grignard addition
allylic halogenation
allylic strain 1,2 & 1,3
alpha effect
ambident anions
amide basicity
amines
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natural compounds
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nomenclature
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primary, secondary & tertiary
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amine oxides
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nitroxide radicals
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preparation of 1º-amines
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preparation of 2º & 3º-amines
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properties
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acidity
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basicity
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boiling points & solubility
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reactions
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amine oxide elimination
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aryl amines & nitrous acid
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Cope elimination
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the Hinsberg test
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Hofmann elimination
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reaction with nitrous acid
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substitution at nitrogen
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substitution & elimination of nitrogen
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structure-formula relationship
amino acids see proteins
aminolysis
amphiphilic & amphipathic
amphoterism
amylose
anandamide
anchimeric assistance
angle strain
anion solvation
anion stability order
anionic rearrangements
anisotropy
annulenes
anomers see carbohydrates
anomeric effect
antarafacial & suprafaciaL
anthracene
anti conformer
anti-syn stereo nomenclature
anti-syn addition
antiaromaticity
aromatic stabilization
aromaticity
aromaticity principles
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aromatic 5-membered heterocycles
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aromatic 6-membered heterocycles
arrows, use of different kinds
aryl diazonium salts
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substitution reactions
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coupling reactions
Arndt-Eistert synthesis
asymmetric carbon
asymmetric induction
asymmetry
atomic orbitals
atomization energy
atropine
atropisomers
aufbau principle
axial
azacations
aziridine inversion
 
Baldwin rules
Barton reaction
base pairing
basicity, Brønsted defined
basicity of amines
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of pyridines and related heterocycles
basicity of amides
basic reagents
basicity & nucleophilicity
basicity & solvent effects
Baeyer-Villiger rearrangement
Beckmann rearrangement
Benedict's test
benzene derivative nomenclature
benzene molecular orbitals (animation)
benzene
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electrophilic substitution reactions
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mechanism of electrophilic substitution (animation)
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halogenation, nitration, sulfonation, Friedel-Crafts
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addition reactions
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elimination reactions
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nucleophilic substitution reactions
benzene derivatives-substituent effects
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substitution orientation
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correlation of reactivity and orientation
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disubstituted benzenes
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halobenzene conversion to organometallic compounds
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hydrolysis of aryl sulfonic acids
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modifying substituent influence
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oxidation of alkyl side-chains
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Birch reduction
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reduction of nitro groups & aryl ketones
benzenonium ion
benzoin condensation
benzyl group
benzyl radical
benzylic acid rearrangement
benzyne
beta-elimination
betaine
bicyclic compounds
bilirubin photochemistry
biosynthetic pathways
biotin
biphenyl stereoisomers
Birch reduction
boat conformer
boiling point
bond dipole
bond dipoles and molecular dipole
bond energy
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average bond energy
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bond dissociation energy of C-H
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bond energy and radical stability
bond-breaking
bond-making
borane (diborane)
Bredt's rule
bridged ring compounds
bromination
bromonium ion intermediate
Brønsted theory
Brook rearrangement
buckminsterfullerene
Bürgi-Dunitz trajectory
butane conformers
 
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