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Molecular Orbitals and Organic Chemical Reactions, Student Edition

ISBN: 978-0-470-74660-8
378 pages
December 2009
Molecular Orbitals and Organic Chemical Reactions, Student Edition (0470746602) cover image
Winner of the PROSE Award for Chemistry & Physics 2010

Acknowledging the very best in professional and scholarly publishing, the annual PROSE Awards recognise publishers' and authors' commitment to pioneering works of research and for contributing to the conception, production, and design of landmark works in their fields. Judged by peer publishers, librarians, and medical professionals, Wiley are pleased to congratulate Professor Ian Fleming, winner of the PROSE Award in Chemistry and Physics for Molecular Orbitals and Organic Chemical Reactions.

Molecular orbital theory is used by chemists to describe the arrangement of electrons in chemical structures. It is also a theory capable of giving some insight into the forces involved in the making and breaking of chemical bonds—the chemical reactions that are often the focus of an organic chemist's interest. Organic chemists with a serious interest in understanding and explaining their work usually express their ideas in molecular orbital terms, so much so that it is now an essential component of every organic chemist's skills to have some acquaintance with molecular orbital theory.

Molecular Orbitals and Organic Chemical Reactions is both a simplified account of molecular orbital theory and a review of its applications in organic chemistry; it provides a basic introduction to the subject and a wealth of illustrative examples. In this book molecular orbital theory is presented in a much simplified, and entirely non-mathematical language, accessible to every organic chemist, whether student or research worker, whether mathematically competent or not. Topics covered include:

  • Molecular Orbital Theory
  • Molecular Orbitals and the Structures of Organic Molecules
  • Chemical Reactions — How Far and How Fast
  • Ionic Reactions — Reactivity
  • Ionic Reactions — Stereochemistry
  • Pericyclic Reactions
  • Radical Reactions
  • Photochemical Reactions

Slides for lectures and presentations are available on the supplementary website: www.wiley.com/go/fleming_student

Molecular Orbitals and Organic Chemical Reactions: Student Edition is an invaluable first textbook on this important subject for students of organic, physical organic and computational chemistry.

The Reference Edition edition takes the content and the same non-mathematical approach of the Student Edition, and adds extensive extra subject coverage, detail and over 1500 references. The additional material adds a deeper understanding of the models used, and includes a broader range of applications and case studies. Providing a complete in-depth reference for a more advanced audience, this edition will find a place on the bookshelves of researchers and advanced students of organic, physical organic and computational chemistry. Further information can be viewed here.

"These books are the result of years of work, which began as an attempt to write a second edition of my 1976 book Frontier Orbitals and Organic Chemical Reactions. I wanted to give a rather more thorough introduction to molecular orbitals, while maintaining my focus on the organic chemist who did not want a mathematical account, but still wanted to understand organic chemistry at a physical level. I'm delighted to win this prize, and hope a new generation of chemists will benefit from these books."
-Professor Ian Fleming

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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.

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  • Provides a first course in this important topic
  • Extends the “frontier orbital” approximation of Fleming’s classic “Frontier Orbitals” to encompass the wider field of molecular orbitals.
  • Fully updated with a wealth of recent illustrative examples
  • Includes key references and suggested further reading for students to find out more
  • A greater emphasis is put on chemistry than on quantum mechanics, and the intelligent use of the rules rather than their mathematical derivation.
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"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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February 15, 2010
Molecular Orbitals and Organic Chemical Reactions: Student Edition

The long-awaited sequel to the classic textbook Frontier Orbitals is now published by Wiley-Blackwell. Molecular Orbitals and Organic Chemical Reactions:  Student Edition is presented in a student-friendly first-course edition.

For most practical purposes, chemists need simple methods which allow them to make general predictions about chemical structure and reactivity. Molecular orbital theory is the most valuable of these methods, used by chemists to describe the arrangement of electrons in chemical structures, whilst also giving insight into the forces involved in the making and breaking of chemical bonds—the chemical reactions that are often the focus of an organic chemist's interest.

Molecular Orbitals and Organic Chemical Reactions:  Student Edition is both a simplified account of molecular orbital theory and a review of its applications in organic chemistry. It provides a basic introduction to the subject and a wealth of illustrative examples. Ian Fleming presents molecular   orbital theory in a much simplified and entirely non-mathematical language, accessible to every organic chemist, whether student or research worker, whether mathematically competent or not.

Organic chemists with a serious interest in understanding and explaining their work usually express their ideas in molecular orbital terms, so much so that it is now an essential component of every organic chemist's skills to have some acquaintance with molecular orbital theory. Now a key component of all chemistry degree courses, it is taught as part of the organic and physical chemistry core syllabus in the first two years, and is often offered as an advanced elective course in the final year.

Molecular Orbitals and Organic Chemical Reactions:  Student Edition provides an essential understanding of the subject for all computational chemists, organic chemists and physical chemists.

 

 

Contents

Molecular Orbital Theory
The Structures of Organic Molecules

Chemical Reactions--How Far and How Fast

Ionic Reactions--Reactivity

Ionic Reactions--Stereochemistry

Pericyclic Reactions

Radical Reactions

Photochemical Reactions

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