Preface.
1 Molecular Orbital Theory.
1.1 The Atomic Orbitals of a Hydrogen Atom.
1.2 Molecules made from Hydrogen Atoms.
1.3 C—H and C—C Bonds.
1.4 Conjugation—Hückel Theory.
1.5 Aromaticity.
1.6 Strained σ Bonds—Cyclopropanes and Cyclobutanes.
1.7 Heteronuclear Bonds, C—M, C—X and C=O.
1.8 The Tau Bond Model.
1.9 Spectroscopic Methods.
1.10 Exercises.
2 The Structures of Organic Molecules.
2.1 The Effects of π Conjugation.
2.2 σ Conjugation—Hyperconjugation.
2.3 The Configurations and Conformations of Molecules.
2.4 Other Noncovalent Interactions.
2.5 Exercises.
3 Chemical Reactions—How Far and How Fast.
3.1 Factors Affecting the Position of an Equilibrium.
3.2 The Principle of Hard and Soft Acids and Bases (HSAB).
3.3 Transition Structures.
3.4 The Perturbation Theory of Reactivity.
3.5 The Salem-Klopman Equation.
3.6 Hard and Soft Nucleophiles and Electrophiles.
3.7 Other Factors Affecting Chemical Reactivity.
4 Ionic Reactions—Reactivity.
4.1 Single Electron Transfer (SET) in Ionic Reactions.
4.2 Nucleophilicity.
4.3 Ambident Nucleophiles.
4.4 Electrophilicity.
4.5 Ambident Electrophiles.
4.6 Carbenes.
4.7 Exercises.
5 Ionic Reactions—Stereochemistry.
5.1 The Stereochemistry of the Fundamental Organic Reactions.
5.2 Diastereoselectivity.
5.3 Exercises.
6 Thermal Pericyclic Reactions.
6.1 The Four Classes of Pericyclic Reactions.
6.2 Evidence for the Concertedness of Bond Making and Breaking.
6.3 Symmetry-Allowed and Symmetry-Forbidden Reactions.
6.4 Explanations for the Woodward-Hoffmann Rules.
6.5 Secondary Effects.
6.6 Exercises.
7 Radical Reactions.
7.1 Nucleophilic and Electrophilic Radicals.
7.2 The Abstraction of Hydrogen and Halogen Atoms.
7.3 The Addition of Radicals to π Bonds
7.4 Synthetic Applications of the Chemoselectivity of Radicals.
7.5 Stereochemistry in some Radical Reactions.
7.6 Ambident Radicals.
7.7 Radical Coupling.
7.8 Exercises.
8 Photochemical Reactions.
8.1 Photochemical Reactions in General.
8.2 Photochemical Ionic Reactions.
8.3 Photochemical Pericyclic Reactions and Related Stepwise Reactions.
8.4 Photochemically Induced Radical Reactions.
8.5 Chemiluminescence.
8.6 Exercises.
References.
Index.
Professor Ian Fleming, Department of Chemistry, University of
Cambridge
Ian Fleming is an Emeritus Professor in the Department of Chemistry
in the University of Cambridge, and an Emeritus Fellow of Pembroke
College. He is the author of five textbooks: Spectroscopic Methods
in Organic Chemistry (McGraw Hill, now in its 6th edition),
Spectroscopic Problems in Organic Chemistry (McGraw Hill); Selected
Organic Syntheses (Wiley), Frontier Orbitals and Organic Chemical
Reactions (Wiley) and Pericyclic Reactions (OUP Oxford Chemistry
Primer series).
"Fleming uses nonquantitative molecular orbital theory to explain
many common phenomena in organic chemistry. As such, this is a very
powerful tool for students of advanced organic chemistry. Much of
what is taken simply on faith or with some hand waving in sophomore
organic chemistry can be readily explained with molecular orbital
theory, which is usually considered too advanced for students at
that level. Though this book could be used as theprimary textbook
for a course solely on molecular orbitals in organic chemistry, it
will more likely be used as a reference source for an advanced
organic chemistry course for upper-level undergraduates or graduate
students." (CHOICE, August 2010)
"The new 'Fleming' is a must for every lecturer and every student
of chemistry—a fantastic book. In this new form the textbook will
last for another 30 years and remain as fresh as did its
predecessor!" (Angewandte Chemie International Edition March 2010)
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