Virtual Textbook of Organic Chemistry

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/VirtTxtJml/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


Concerning Practice Problems

The practice problems provided as part of this text are chiefly interactive, and should provide a useful assessment of the reader's understanding at various stages in the development of the subject. Some of these problems make use of a Molecular Editor drawing application created by Peter.Ertl. To practice using this editor Click Here.
Since problem solving is essential to achieving an effective mastery of the subject, it is recommended that many more problems be worked. Most organic chemistry textbooks contain a broad assortment of suitable problems, and paperback collections of practice problems are also available. In addition, a large collection of multiple choice problems may be viewed Here.
The following button will activate a collection of problems concerning the reactivity of common functional groups.
The following web-sites provide nice collections of problems and answers:
Towson University-reaction quizzes and summaries
Ohio State University-electronic flashcards
University of Wisconsin-concept questions
UCLA-practice problems
Notre Dame-spectroscopy problems
For a useful collection of study materials, including links to other sites, visit the Organic chemistry tool-kit. Prepared by Bob Hanson, St. Olaf College

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
Practice Problems



Alphabetical Index

[ A ][ B ][ C ][ D ][ E ][F-G][ H ][I-K][ L ][ M ][N-O][ P ][Q-R][ S ][ T ][U-V][W-Z]These pages are the property of William Reusch.
©1999 William Reusch, All rights reserved (most recent revision 7/16/2007)
Comments, questions and errors should be sent to whreusch@msu.edu.

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