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Molecular Orbitals and Organic Chemical Reactions

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ISBN-10: 0470746599

ISBN-13: 9780470746592

Edition: 2009 (Student Manual, Study Guide, etc.)

Authors: Ian Fleming

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Description:

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 bondsthe 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 ReactionsMolecular Orbitals and Organic Chemical Reactions: An Introduction is an invaluable first textbook on this important subject for students of organic, physical organic and computational chemistry.
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Book details

Copyright year: 2009
Publisher: John Wiley & Sons, Limited
Publication date: 11/20/2009
Binding: Paperback
Pages: 376
Size: 5.75" wide x 8.75" long x 0.75" tall
Weight: 1.232

Ian Lancaster Fleming was born on May 28, 1908, in London, England. He attended Eton College and then the Royal Military College at Sandhurst. He left there after a year to go study languages in Munich and Geneva. Fleming served as the Moscow correspondent for the Reuters News Agency from 1929 till 1933. he then became a banker and a stockholder in London until the beginning of World War II. When the war began, Fleming became the personal assistant to the Director of British Naval Intelligence, where he learned most of his espionage terms. When the war was over, he worked as the foreign manager of The Sunday Times in London. Fleming wrote twelve James Bond novels, nearly all of which were made into Motion Pictures. His works included: Casino Royale, Live and Let Die, Moonraker, Diamonds Are Forever, Dr. No, Goldfinger, Thunderball, Chitty-Chitty-Bang-Bang, and For Your eyes Only. He of died of a heart attack on August 12, 1964.

Preface
Molecular Orbital Theory
The Atomic Orbitals of a Hydrogen Atom
Molecules made from Hydrogen Atoms
The H<sub>2</sub> Molecule
The H<sub>3</sub> Molecule
The H<sub>4</sub> �Molecule�
C-H and C-C Bonds
The Atomic Orbitals of a Carbon Atom
Methane
Methylene
Hybridisation
C-C � Bonds and � Bonds: Ethane
C=C � Bonds: Ethylene
Conjugation-H�ckel Theory
The Allyl System
Butadiene
Longer Conjugated Systems
Aromaticity
Aromatic Systems
Antiaromatic Systems
The Cyclopentadienyl Anion and Cation
Homoaromaticity
Spiro Conjugation
Strained � Bonds-Cyclopropanes and Cyclobutanes
Cyclopropanes
Cyclobutanes
Heteronuclear Bonds, C-M, C-X and C=O
Atomic orbital energies and electronegativity
C-X � Bonds
C-M � Bonds
C=O � Bonds
Heterocyclic Aromatic Systems
The Tau Bond Model
Spectroscopic Methods
Ultraviolet Spectroscopy
Photoelectron Spectroscopy
Nuclear Magnetic Resonance Spectroscopy
Electron Spin Resonance Spectroscopy
Exercises
The Structures of Organic Molecules
The Effects of � Conjugation
A Notation for Substituents
The Effect of Substituents on the Stability of Alkenes
The Effect of Substituents on the Stability of Carbocations
The Effect of Substituents on the Stability of Carbanions
The Effect of Substituents on the Stability of Radicals
Energy-Raising Conjugation
� Conjugation-Hyperconjugation
C-H and C-C Hyperconjugation
C-M Hyperconjugation
Negative Hyperconjugation
The Configurations and Conformations of Molecules
Restricted Rotation in �-Conjugated Systems
Preferred Conformations from Conjugation in the � Framework
Other Noncovalent Interactions
The Hydrogen Bond
Hypervalency
Polar Interactions, and van der Waals and other Weak Interactions
Exercises
Chemical Reactions-How Far and How Fast
Factors Affecting the Position of an Equilibrium
The Principle of Hard and Soft Acids and Bases (HSAB)
Transition Structures
The Perturbation Theory of Reactivity
The Salem-Klopman Equation
Hard and Soft Nucleophiles and Electrophiles
Other Factors Affecting Chemical Reactivity
Ionic Reactions-Reactivity
Single Electron Transfer (SET) in Ionic Reactions
Nucleophilicity
Heteroatom Nucleophiles
Solvent Effects
Alkene Nucleophiles
The �-Effect
Ambident Nucleophiles
Thiocyanate Ion, Cyanide Ion and Nitrite Ion (and the Nitronium Cation)
Enolate Ions
Allyl Anions
Aromatic Electrophilic Substitution
Electrophilicity
Trigonal Electrophiles
Tetrahedral Electrophiles
Hard and Soft Electrophiles
Ambident Electrophiles
Aromatic Electrophiles
Aliphatic Electrophiles
Carbenes
Nucleophilic Carbenes
Electrophilic Carbenes
Aromatic Carbenes
Exercises
Ionic Reactions-Stereochemistry
The Stereochemistry of the Fundamental Organic Reactions
Substitution at a Saturated Carbon
Elimination Reactions
Nucleophilic and Electrophilic Attack on a � Bond
The Stereochemistry of Substitution at Trigonal Carbon
Diastereoselectivity
Nucleophilic Attack on a Double Bond with Diastereotopic Faces
Nucleophilic and Electrophilic Attack on Cycloalkenes
Electrophilic Attack on Open-Chain Double Bonds with Diastereotopic Faces
Diastereoselective Nucleophilic and Electrophilic Attack on Double Bonds Free of Steric Effects
Exercises
Thermal Pericyclic Reactions
The Four Classes of Pericyclic Reactions
Evidence for the Concertedness of Bond Making and Breaking
Symmetry-Allowed and Symmetry-Forbidden Reactions
The Woodward-Hoffmann Rules-Class by Class
The Generalised Woodward-Hoffmann Rule
Explanations for the Woodward-Hoffmann Rules
The Aromatic Transition Structure
Frontier Orbitals
Correlation Diagrams
Secondary Effects
The Energies and Coefficients of the Frontier Orbitals of Alkenes and Dienes
Diels-Alder Reactions
1,3-Dipolar Cycloadditions
Other Cycloadditions
Other Pericyclic Reactions
Periselectivity
Torquoselectivity
Exercises
Radical Reactions
Nucleophilic and Electrophilic Radicals
The Abstraction of Hydrogen and Halogen Atoms
The Effect of the Structure of the Radical
The Effect of the Structure of the Hydrogen or Halogen Source
The Addition of Radicals to � Bonds
Attack on Substituted Alkenes
Attack on Substituted Aromatic Rings
Synthetic Applications of the Chemoselectivity of Radicals
Stereochemistry in some Radical Reactions
Ambident Radicals
Neutral Ambident Radicals
Charged Ambident Radicals
Radical Coupling
Exercises
Photochemical Reactions
Photochemical Reactions in General
Photochemical Ionic Reactions
Aromatic Nucleophilic Substitution
Aromatic Electrophilic Substitution
Aromatic Side-Chain Reactivity
Photochemical Pericyclic Reactions and Related Stepwise Reactions
The Photochemical Woodward-Hoffmann Rule
Regioselectivity of Photocycloadditions
Other Kinds of Selectivity in Pericyclic and Related Photochemical Reactions
Photochemically Induced Radical Reactions
Chemiluminescence
Exercises
References
Index