Virtual Textbook of Organic Chemistry


Organic chemistry is most commonly and simply defined as the chemistry of carbon compounds. Carbon is not an abundant element in the universe, or even the solar system; but it is an essential element of life. Indeed, four elements: carbon, hydrogen, nitrogen and oxygen make up most of the matter found in living organisms. Trace elements such as sulfur, phosphorous, sodium, potassium and iron, to name a few, also play an important role in the chemistry of life; but it is the unique properties of carbon that permits the immense diversity of compounds associated with life. From simple single-carbon compounds such as methane and carbon dioxide to the more complex structures found in vitamins, hormones and enzymes, and ultimately to very large macromolecules like DNA, carbon is the underlying essential structural component.

Since the birth of organic chemistry over two hundred years ago, chemists have worked to unravel the structural complexities of these compounds. Today, all the facts and principles they have learned are consolidated in our texts and journals. Industrial applications have led to the manufacture of medicinal agents (drugs), synthetic fibers, plastics, dyes, pesticides and a host of other useful materials. Clearly, organic chemistry has touched all our lives. The study of organic chemistry is both fascinating and relevant, due in large part to the widespread distribution of both natural and synthetic organic chemicals.

Table of Contents

I. Getting Started     Advice for the Beginning Student

II. Some Basic Principles
Structure & Bonding
Electron Configurations of Atoms
Chemical Bonding & Valence
Charge Distribution in Molecules
Practice Problems 1
The Shape of Molecules
Analysis of Molecular Formulas
Atomic and Molecular Orbitals
Practice Problems 2
Intermolecular Forces
Boiling & Melting Points
Hydrogen Bonding
Water Solubility
Practice Problems 2b

Chemical Reactivity
Reaction Classification
By Structural Change
By Reaction Type
Acid-Base Reactions
Oxidations & Reductions
By Functional Group
Reaction Characteristics
Product Selectivity
Reaction Rate
Reaction Energetics
Bond Energy
More about Energy
Reaction Mechanisms
Curved Arrow Notation
Reactive Intermediates
Reaction Illustrations
Nucleophilicity & Basicity
Acid-Base Catalysis
Practice Problems 3
Other Aromatic Compounds & The Hückel Rule
Practice Problems 3b
Practice Problems 4
Alkenes & Alkynes
Substituted Benzenes
Other Functional Groups
Practice Problems 5

Stereoisomers Part I
Alkene Configurational Isomers
Cycloalkane Configurational Isomers
Practice Problems 6
Conformational Isomers
Substituted Cycloalkanes
Practice Problems 7
Stereoisomers Part II
Chirality & Symmetry
Structural Analysis by Symmetry Elements
Optical Activity
Configurational Nomenclature
Compounds Having Two or More Stereogenic Centers
Stereogenic Nitrogen
Fischer Projection Formulas
Achiral Diastereomers
Other Configurational Notations
Conformational Enantiomorphism
Practice Problems 8
Summary of Isomerism

III. Functional Group Chemistry     The second part of this text

IV. Spectroscopy     The third part of this text

VI. Molecules of Biological Interest     The fourth part of this text

V. Special Topics
Free Radicals
Pericyclic Reactions
Rearrangements to Cationic Sites

At various points throughout this text, links to supplementary information or special topics will be located in shaded boxes of this kind.

Alphabetical Index for Virtual Textbook of Organic Chemistry

[ A ]    [ B ]    [ C ]    [ D ]    [ E ]    [ F-G ]    [ H ]    [ I-K ]    [ L ]    [ M ]    [ N-O ]    [ P ]    [ Q-R ]    [ S ]    [ T ]    [ U-V ]    [ W-Z ]

These materials may be used in a formal course of organic chemistry in a variety of ways. Because of the modular structure of this text, it is easy to pick and choose the subjects to be treated, as well as the depth of coverage. Numerous anchors on all the pages of this text allow tailoring the material to a suit many ends. An example of a short course table of contents may be examined by Clicking Here.

These pages are the property of William Reusch.
©1999 William Reusch, All rights reserved.
(most recent revision 9/30/2002)
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