March's Advanced Organic Chemistry Reactions, Mechanisms, and Structure

ISBN-10: 0470462590
ISBN-13: 9780470462591
Edition: 7th 2013
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Description: The definitive resource for students and professionals in organic chemistry, the Seventh Edition of March′s Advanced Organic Chemistry continues to prove to be a must–have resource for planning and execution of synthetic reactions. Each chapter has  More...

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Book details

List price: $83.50
Edition: 7th
Copyright year: 2013
Publisher: John Wiley & Sons, Limited
Publication date: 5/17/2013
Binding: Hardcover
Pages: 2080
Size: 8.00" wide x 10.50" long x 3.00" tall
Weight: 3.718
Language: English

The definitive resource for students and professionals in organic chemistry, the Seventh Edition of March′s Advanced Organic Chemistry continues to prove to be a must–have resource for planning and execution of synthetic reactions. Each chapter has been updated to reflect the most recent reaction information with references to both the primary and review literature. Heavily revised throughout, this seventh edition clearly explains the theories and examples of organic chemistry and guides readers on planning and execution of multi–step synthetic reactions, with detailed descriptions of all the reactions.

Preface
Biographical Statement
Localized Chemical Bonding
Covalent Bonding
Multiple Valence
Hybridization
Multiple Bonds
Photoelectron Spectroscopy
Electronic Structures Of Molecules
Electronegativity
Dipole Moment
Inductive And Field Effects
Bond Distances
Bond Angles
Bond Energies
Delocalized Chemical Bonding
Molecular Orbitals
Bond Energies and Distances in Compounds Containing Delocalized Bonds
Molecules That Have Delocalized Bonds
Cross Conjugation
The Rules Of Resonance
The Resonance Effect
Steric Inhibition Of Resonance And The Influences Of Strain
P�-D� Bonding.Ylids
Aromaticity
Six-Membered Rings
Five, Seven, and Eight-Membered Rings
Other Systems Containing Aromatic Sextets
Alternant And Nonalternant Hydrocarbons
Aromatic Systems With Electron Numbers Other Than Six
Systems of Two Electrons
Systems of Four Electrons: Antiaromaticity
Systems of Eight Electrons
Systems of Ten Electrons
Systems of More than Ten Electrons: 4n + 2 Electrons
Systems of More Than Ten Electrons: 4n Electrons
Other Aromatic Compounds
Hyperconjugation
Tautomerism
Keto-Enol Tautomerism
Other Proton-Shift Tautomerism
Valence Tautomerism
Bonding Weaker than Covalent
Hydrogen Bonding
?-? Interactions
Addition Compounds
Electron Donor-Acceptor (EDA) Complexes
Crown Ether Complexes and Cryptates
Inclusion Compounds
Cyclodextrins
Catenanes and Rotaxanes
Cucurbit[n]uril-Based Gyroscane
Stereochemistry and Conformation
Optical Activity and Chirality
Dependence of Rotation on Conditions of Measurement
What Kinds of Molecules Display Optical Activity?
The Fischer Projection
Absolute Configuration
The Cahn-Ingold-Prelog System
Methods of Determining Configuration
Cis-Trans Isomerism Resulting from Double Bonds
Cis-Trans Isomerism of Monocyclic Compounds
Cis-Trans Isomerism of Fused and Bridged Ring Systems
Out-In Isomerism
Enantiotopic and Diastereotopic Atoms, Groups, and Faces
Stereospecific and Stereoselective Syntheses
Conformational Analysis
Conformation in Open-Chain Systems
Conformation in Six-Membered Rings
Conformation in Six-Membered Rings Containing Heteroatoms
Conformation in Other Rings
Molecular Mechanics
Strain
Strain in Small Rings
Strain in Other Rings
Unsaturated Rings
Strain Due to Unavoidable Crowding
Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes
Carbocations
Nomenclature
Stability and Structure of Carbocations
The Generation and Fate of Carbocations
Carbanions
Stability and Structure
The Structure of Organometallic Compounds
Free Radicals
Stability and Structure
The Generation and Fate of Free Radicals
CARBENES
Stability and Structure
The Generation and Fate of Carbenes
Nitrenes
Mechanisms and Methods of Determining them
Types Of Mechanism
Types Of Reaction
Thermodynamic Requirements for Reaction
Kinetic Requirements for Reaction
The Baldwin Rules for Ring Closure
Kinetic and Thermodynamic Control
The Hammond Postulate
Microscopic Reversibility
Marcus Theory
Methods of Determining Mechanisms
Identification of Products
Determination of the Presence of an Intermediate
The Study of Catalysis
Isotopic Labeling
Stereochemical Evidence
Kinetic Evidence
Isotope Effects
Irradiation Processes in Organic Chemistry
Photochemistry
Excited States and the Ground State
Singlet and Triplet States: "Forbidden" Transitions
Types of Excitation
Nomenclature and Properties of Excited States
Photolytic Cleavage
The Fate of the Excited Molecule: Physical Processes
The Fate of the Excited Molecule: Chemical Processes
The Determination of Photochemical Mechanisms
Sonochemistry
Microwave Chemistry
Acids and Bases
Br?nsted Theory
Bronsted Acids
Bronsted Bases
The Mechanism of Proton Transfer Reactions
Measurements of Solvent Acidity
Acid and Base Catalysis
Lewis Acids and Bases
Hard and Soft Acids and Bases
The Effects of Structure on the Strengths of Acids and Bases
The Effects of the Medium on Acid and Base Strength
Effects of Structure and Medium on Reactivity
Resonance and Field Effects
Steric Effects
Quantitative Treatments of the Effect of Structure on Reactivity
Effect of Medium on Reactivity and Rate
High Pressure
Water and Other Non-Organic Solvents
Ionic Solvents
Solventless Reactions
Iupac Nomenclature for Transformations
Substitutions
Additions
Iupac System for Symbolic Representation of Mechanisms
Organic Syntheses References
Aliphatic Substitution, Nucleophilic and Organometallic
Mechanisms
The SN2 Mechanism
The SN1 Mechanism
Ion Pairs in the SN1 Mechanism
Mixed SN1 and SN2 Mechanisms
SET Mechanisms
The Neighboring-Group Mechanism
Neighboring-Group Participation by � and ? Bonds: Nonclassical Carbocations
The SNi Mechanism
Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements
Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism
Reactivity
The Effect of Substrate Structure
The Effect of the Attacking Nucleophile
The Effect of the Leaving Group
The Effect of the Reaction Medium
Phase-Transfer Catalysis
Influencing Reactivity by External Means
Ambident (Bidentant) Nucleophiles: Regioselectivity
Ambident Substrates
Reactions
Oxygen Nucleophiles
Sulfur Nucleophiles
Nitrogen Nucleophiles
Halogen Nucleophiles
Carbon Nucleophiles
Aromatic Substitution, Electrophilic
Mechanisms
The Arenium Ion Mechanism
The SE1 Mechanism
Orientation and Reactivity
Orientation and Reactivity in Monosubstituted Benzene Rings
The Ortho/Para Ratio
Ipso Attack
Orientation in Benzene Rings With More Than One Substituent
Orientation in Other Ring Systems
Quantitative Treatments of Reactivity in the Substrate
A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship
The Effect of the Leaving Group
Reactions
Hydrogen as the Leaving Group in Simple Substitution Reactions
Hydrogen as the Leaving Group in Rearrangement Reactions
Other Leaving Groups
Aliphatic, Alkenyl, and Alkynyl Substitution, Electrophilic and Organometallic
Mechanisms
Bimolecular Mechanisms. SE2 and SEi
The SE1 Mechanism
Electrophilic Substitution Accompanied by Double-Bond Shifts
Other Mechanisms
Reactivity
REACTIONS
Hydrogen as Leaving Group
Metals as Leaving Groups
Halogen as Leaving Group
Carbon Leaving Groups
Electrophilic Substitution at Nitrogen
Aromatic Substitution, Nucleophilic and Organometallic
Mechanisms
The SNAr Mechanism
The SN1 Mechanism
The Benzyne Mechanism
The SRN1 Mechanism
Other Mechanisms
Reactivity
The Effect of Substrate Structure
The Effect of the Leaving Group
The Effect of the Attacking Nucleophile
Reactions
All Leaving Groups Except Hydrogen and N2+
Hydrogen as Leaving Group
Nitrogen as Leaving Group
Rearrangements
Substitution Reactions, Radical
Mechanisms
Radical Mechanisms in General
Free-Radical Substitution Mechanisms
Mechanisms at an Aromatic Substrate
Neighboring-Group Assistance in Free-Radical Reactions
Reactivity
Reactivity for Aliphatic Substrates
Reactivity at a Bridgehead
Reactivity in Aromatic Substrates
Reactivity in the Attacking Radical
The Effect of Solvent on Reactivity
Reactions
Hydrogen as Leaving Group
N2 as Leaving Group
Metals as Leaving Groups
Halogen as Leaving Group
Sulfur as Leaving Group
Carbon as Leaving Group
Addition to Carbon-Carbon Multiple Bonds
Mechanisms
Electrophilic Addition
Nucleophilic Addition
Free-Radical Addition
Cyclic Mechanisms
Orientation And Reactivity
Reactivity
Orientation
Stereochemical Orientation
Addition to Cyclopropane Rings
Reactions
Isomerization Of Double And Triple Bonds
Reactions In Which Hydrogen Adds To One Side
Reactions In Which Hydrogen Adds To Neither Side
Cycloaddition Reactions
Addition to Carbon-Hetero Multiple Bonds
Mechanism and Reactivity
Nucleophilic Substitution at an Aliphatic Trigonal Carbon. The Tetrahedral Mechanism
Reactions
Reactions In Which Hydrogen Or A Metallic Ion Adds To The Heteroatom
Acyl Substitution Reactions
Reactions In Which Carbon Adds To The Heteroatom
Addition To Isocyanides
Nucleophilic Substitution At A Sulfonyl Sulfur Atom
Eliminations
Mechanisms and Orientation
The E2 Mechanism
The E1 Mechanism
The E1cB Mechanism
The E1-E2-E1cB Spectrum
The E2C Mechanism
Regiochemistry of the Double Bond
Stereochemistry of the Double Bond
Reactivity
Effect of Substrate Structure
Effect of the Attacking Base
Effect of the Leaving Group
Effect of the Medium
Mechanisms and Orientation in Pyrolytic Eliminations
Mechanisms
Orientation in Pyrolytic Eliminations
1,4 Conjugate Eliminations
Reactions
Reactions In Which C=C And C?C Bonds Are Formed
Fragmentations
Reactions In Which C?N Or C=N Bonds Are Formed
Reactions In Which C=O Bonds Are Formed
Reactions In Which N=N Bonds Are Formed
Extrusion Reactions
Rearrangements
Mechanisms
Nucleophilic Rearrangements
The Actual Nature of the Migration
Migratory Aptitudes
Memory Effects
Longer Nucleophilic Rearrangements
Free-Radical Rearrangements
Carbene Rearrangements
Electrophilic Rearrangements
Reactions
1,2-Rearrangements
Non-1,2 Rearrangements
Oxidations and Reductions
Mechanisms
Reactions
Oxidations
Reductions
The Literature of Organic Chemistry
Primary Sources
Journals
Patents
Secondary Sources
Listings of Titles
Abstracts
Beilstein
Tables of Information
Reviews
Annual Reviews
Awareness Services
General Treatises
Monographs and Treatises on Specific Areas
Textbooks
Other Books
Literature Searching
Literature Searching Using Printed Materials
Literature Searching Online
Sci-Finder - the CAS database
Science Citation Index
How to Locate Journal Articles
Reaxys
Classification of Reactions by Type of Compounds Synthesized
Author Index
Index

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