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March's advanced organic chemistry : reactions, mechanisms, and structure / Michael B. Smith.

Smith, Michael B.
Material type: materialTypeLabelBook; Format: print Publisher: Hoboken : Wiley, 2013Edition: 7th ed.Description: XXV, 2047 p. ; 27 cm.ISBN: 9780470462591.Other title: Advanced organic chemistry.Subject(s): Química orgánica
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QUÍMICA ORGÁNICA AVANZADA GRADO EN QUÍMICA Asignatura actualizada 2017-2018

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Enhanced descriptions from Syndetics:

The new, revised and updated 7th edition of March's Advanced Organic Chemistry clearly explainsthe theories and examples of organic chemistry, providing the mostcomprehensive resource about organic chemistry available.

Readers are guided on planning and execution of multi-stepsynthetic reactions, with detailed descriptions of all thereactions. The first five chapters deal with the structure oforganic compounds and discuss important organic chemistrybonds, fundamental principles of conformation, and stereochemistryof organic molecules, and reactive intermediates in organicchemistry. Chapters 6 to 9 are concerned with generalprinciples of mechanism in organic chemistry, including acids andbases, photochemistry, sonochemistry and microwave irradiation, andfinally the relationship between structure and reactivity. Thelast 10 chapters cover the nature and the scope of organicreactions and their mechanisms.

The 7th edition proves again it is a must-havedesktop reference and textbook for every student and professionalworking in organic chemistry or related fields.

Key features of the 7th edition:

Every chapter has been updated with the most recent reactioninformation with references to both the primary and reviewliterature New to the 7th edition: 5,500 references since the lastedition, updates / rewrites of the retained sections, and anupdated index in Appendix B Contains more than 1650 reactions and 20,000 valuablereferences to the primary literature Includes appendices on the literature of organic chemistry andthe classification of reactions according to the compoundssynthesized Guides the reader on planning and execution of multi-stepsynthetic reactions, with detailed descriptions of all thereactions.

Reviews of the previous edition:

"...a favorite general organic chemistry text and an easy-to-useone-volume reference. We are confident that this book will remain adominant reference and that it will reside on many chemists'personal bookshelves." - Journal of MedicinalChemistry

"Who can hope to be seriously accepted as a member of theorganic chemistry community without being in possession of at leastone edition of 'March'?" - Chemistry and Industry

Table of contents provided by Syndetics

  • Preface
  • Biographical Statement
  • Part 1
  • Chapter 1 Localized Chemical Bonding
  • 1.A Covalent Bonding
  • 1.B Multiple Valence
  • 1.C Hybridization
  • 1.D Multiple Bonds
  • 1.E Photoelectron Spectroscopy
  • 1.F Electronic Structures Of Molecules
  • 1.G Electronegativity
  • 1.H Dipole Moment
  • 1.I Inductive And Field Effects
  • 1.J Bond Distances
  • 1 K Bond Angles
  • 1.L Bond Energies
  • Chapter 2 Delocalized Chemical Bonding
  • 2.A Molecular Orbitals
  • 2.B Bond Energies and Distances in Compounds Containing Delocalized Bonds
  • 2.C Molecules That Have Delocalized Bonds
  • 2.D Cross Conjugation
  • 2.E The Rules Of Resonance
  • 2.F The Resonance Effect
  • 2.G Steric Inhibition Of Resonance And The Influences Of Strain
  • 2.H P¿-D¿ Bonding.Ylids
  • 2.I Aromaticity
  • 2.I.i Six-Membered Rings
  • 2.I.ii Five, Seven, and Eight-Membered Rings
  • 2.I.iii Other Systems Containing Aromatic Sextets
  • 2.J Alternant And Nonalternant Hydrocarbons
  • 2.K Aromatic Systems With Electron Numbers Other Than Six
  • 2.K.i Systems of Two Electrons
  • 2.K.ii Systems of Four Electrons: Antiaromaticity
  • 2.K.iii Systems of Eight Electrons
  • 2.K.iv Systems of Ten Electrons
  • 2.K.v Systems of More than Ten Electrons: 4n + 2 Electrons
  • 2.K.vi Systems of More Than Ten Electrons: 4n Electrons
  • 2.L Other Aromatic Compounds
  • 2.M Hyperconjugation
  • 2.N Tautomerism
  • 2.N.i Keto-Enol Tautomerism
  • 2.N.ii Other Proton-Shift Tautomerism
  • 2.N.iii Valence Tautomerism
  • 3 Bonding Weaker than Covalent
  • 3.A Hydrogen Bonding
  • 3.B ?-? Interactions
  • 3.C Addition Compounds
  • 3.C.i Electron Donor-Acceptor (EDA) Complexes
  • 3.C.ii Crown Ether Complexes and Cryptates
  • 3.C.iii Inclusion Compounds
  • 3.C.iv Cyclodextrins
  • 3.D Catenanes and Rotaxanes
  • 3.E Cucurbit[n]uril-Based Gyroscane
  • 4 Stereochemistry and Conformation
  • 4.A Optical Activity and Chirality
  • 4.B Dependence of Rotation on Conditions of Measurement
  • 4.C What Kinds of Molecules Display Optical Activity?
  • 4.D The Fischer Projection
  • 4.E Absolute Configuration
  • 4.E.i The Cahn-Ingold-Prelog System
  • 4.E.ii Methods of Determining Configuration
  • 4.F.The Cause of Optical Activity
  • 4.G.Molecules With More Than One Stereogenic Center
  • 4.H.Asymmetric Synthesis
  • 4.I.Methods of Resolution
  • 4.J.Optical Purity
  • 4.K.Cis-Trans Isomerism
  • 4.K.i Cis-Trans Isomerism Resulting from Double Bonds
  • 4.K.ii Cis-Trans Isomerism of Monocyclic Compounds
  • 4.K.iii Cis-Trans Isomerism of Fused and Bridged Ring Systems
  • 4.L Out-In Isomerism
  • 4.M Enantiotopic and Diastereotopic Atoms, Groups, and Faces
  • 4.N Stereospecific and Stereoselective Syntheses
  • 4.O Conformational Analysis
  • 4.O.i Conformation in Open-Chain Systems
  • 4.O.ii Conformation in Six-Membered Rings
  • 4.O.iii Conformation in Six-Membered Rings Containing Heteroatoms
  • 4.O.iv Conformation in Other Rings
  • 4.P Molecular Mechanics
  • 4.Q Strain
  • 4.Q.i Strain in Small Rings
  • 4.Q.ii Strain in Other Rings
  • 4.Q.iii Unsaturated Rings
  • 4.Q.iv Strain Due to Unavoidable Crowding
  • 5 Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes
  • 5.A Carbocations
  • 5.A.i Nomenclature
  • 5.A.ii Stability and Structure of Carbocations
  • 5.A.iii The Generation and Fate of Carbocations
  • 5.B Carbanions
  • 5.B.i Stability and Structure
  • 5.B.ii The Structure of Organometallic Compounds
  • 5.B.iii|Tthe Generation and Fate Of Carbanions
  • 5.C Free Radicals
  • 5.C.i Stability and Structure
  • 5.C.ii The Generation and Fate of Free Radicals
  • 5.C.iii|Tradical Ions
  • 5.D CARBENES
  • 5.D.i Stability and Structure
  • 5.D.ii The Generation and Fate of Carbenes
  • 5.E Nitrenes
  • 6 Mechanisms and Methods of Determining them
  • 6.A Types Of Mechanism
  • 6.B Types Of Reaction
  • 6.C Thermodynamic Requirements for Reaction
  • 6.D Kinetic Requirements for Reaction
  • 6.E The Baldwin Rules for Ring Closure
  • 6.F Kinetic and Thermodynamic Control
  • 6.G The Hammond Postulate
  • 6.H Microscopic Reversibility
  • 6.I Marcus Theory
  • 6.J Methods of Determining Mechanisms
  • 6.J.i Identification of Products
  • 6.J.ii Determination of the Presence of an Intermediate
  • 6.J.iii The Study of Catalysis
  • 6.J.iv Isotopic Labeling
  • 6.J.v Stereochemical Evidence
  • 6.J.vi Kinetic Evidence
  • 6.J.vii Isotope Effects
  • 7 Irradiation Processes in Organic Chemistry
  • 7.A Photochemistry
  • 7.A.i Excited States and the Ground State
  • 7.A.ii Singlet and Triplet States: "Forbidden" Transitions
  • 7.A.iii Types of Excitation
  • 7.A.iv Nomenclature and Properties of Excited States
  • 7.A.v Photolytic Cleavage
  • 7.A.vi The Fate of the Excited Molecule: Physical Processes
  • 7.A.vii The Fate of the Excited Molecule: Chemical Processes
  • 7.A.viii The Determination of Photochemical Mechanisms
  • 7.B Sonochemistry
  • 7.C Microwave Chemistry
  • 8 Acids and Bases
  • 8.A Br?nsted Theory
  • 8.A.i Bronsted Acids
  • 8.A.ii Bronsted Bases
  • 8.B The Mechanism of Proton Transfer Reactions
  • 8.C Measurements of Solvent Acidity
  • 8.D Acid and Base Catalysis
  • 8.E Lewis Acids and Bases
  • 8.E.i Hard and Soft Acids and Bases
  • 8.F The Effects of Structure on the Strengths of Acids and Bases
  • 8.G The Effects of the Medium on Acid and Base Strength
  • 9 Effects of Structure and Medium on Reactivity
  • 9.A Resonance and Field Effects
  • 9.B Steric Effects
  • 9.C Quantitative Treatments of the Effect of Structure on Reactivity
  • 9.D Effect of Medium on Reactivity and Rate
  • 9.D.i High Pressure
  • 9.D.ii Water and Other Non-Organic Solvents
  • 9.D.iii Ionic Solvents
  • 9.D.iv Solventless Reactions
  • Part 2
  • 9.E Iupac Nomenclature for Transformations
  • 9.E.i Substitutions
  • 9.E.ii Additions
  • 9.F Iupac System for Symbolic Representation of Mechanisms
  • 9.G Organic Syntheses References
  • 10 Aliphatic Substitution, Nucleophilic and Organometallic
  • 10.A Mechanisms
  • 10.A.i The SN2 Mechanism
  • 10.A.ii The SN1 Mechanism
  • 10.A.iii Ion Pairs in the SN1 Mechanism
  • 10.A.iv Mixed SN1 and SN2 Mechanisms
  • 10.B SET Mechanisms
  • 10.C The Neighboring-Group Mechanism
  • 10.C.i Neighboring-Group Participation by ¿ and ? Bonds: Nonclassical Carbocations
  • 10.D The SNi Mechanism
  • 10.E Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements
  • 10.F Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism
  • 10.G Reactivity
  • 10.G.i The Effect of Substrate Structure
  • 10.G.ii The Effect of the Attacking Nucleophile
  • 10.G.iii The Effect of the Leaving Group
  • 10.G.iv The Effect of the Reaction Medium
  • 10.G.v Phase-Transfer Catalysis
  • 10.G.vi Influencing Reactivity by External Means
  • 10.G.vii Ambident (Bidentant) Nucleophiles: Regioselectivity
  • 10.G.viii Ambident Substrates
  • 10.H Reactions
  • 10.H.i Oxygen Nucleophiles
  • 10.H.ii Sulfur Nucleophiles
  • 10.H.iii Nitrogen Nucleophiles
  • 10.H.iv Halogen Nucleophiles
  • 10.H.v Carbon Nucleophiles
  • 11 Aromatic Substitution, Electrophilic
  • 11.A Mechanisms
  • 11.A.i The Arenium Ion Mechanism
  • 11.A.ii The SE1 Mechanism
  • 11.B Orientation and Reactivity
  • 11.B.i Orientation and Reactivity in Monosubstituted Benzene Rings
  • 11.B.ii The Ortho/Para Ratio
  • 11.B.iii Ipso Attack
  • 11.B.iv Orientation in Benzene Rings With More Than One Substituent
  • 11.B.v Orientation in Other Ring Systems
  • 11.C Quantitative Treatments of Reactivity in the Substrate
  • 11.D A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship
  • 11.E The Effect of the Leaving Group
  • 11.F Reactions
  • 11.F.i Hydrogen as the Leaving Group in Simple Substitution Reactions
  • 11.F.ii Hydrogen as the Leaving Group in Rearrangement Reactions
  • 11.F.iii Other Leaving Groups
  • 12 Aliphatic, Alkenyl, and Alkynyl Substitution, Electrophilic and Organometallic
  • 12.A Mechanisms
  • 12.A.i Bimolecular Mechanisms. SE2 and SEi
  • 12.A.ii The SE1 Mechanism
  • 12.A.iii Electrophilic Substitution Accompanied by Double-Bond Shifts
  • 12.A.iv Other Mechanisms
  • 12.B Reactivity
  • 12.C REACTIONS
  • 12.C.i Hydrogen as Leaving Group
  • 12.C.ii Metals as Leaving Groups
  • 12.C.iii Halogen as Leaving Group
  • 12.C.iv Carbon Leaving Groups
  • 12.C.v Electrophilic Substitution at Nitrogen
  • 13 Aromatic Substitution, Nucleophilic and Organometallic
  • 13.A Mechanisms
  • 13.A.i The SNAr Mechanism
  • 13.A.ii The SN1 Mechanism
  • 13.A.iii The Benzyne Mechanism
  • 13.A.iv The SRN1 Mechanism
  • 13.A.v Other Mechanisms
  • 13.B Reactivity
  • 13.B.i The Effect of Substrate Structure
  • 13.B.ii The Effect of the Leaving Group
  • 13.B.iii The Effect of the Attacking Nucleophile
  • 13.C Reactions
  • 13.C.i All Leaving Groups Except Hydrogen and N2+
  • 13.C.ii Hydrogen as Leaving Group
  • 13.C.iii Nitrogen as Leaving Group
  • 13.C.iv Rearrangements
  • 14 Substitution Reactions, Radical
  • 14.A Mechanisms
  • 14.A.i Radical Mechanisms in General
  • 14.A.ii Free-Radical Substitution Mechanisms
  • 14.A.iii Mechanisms at an Aromatic Substrate
  • 14.A.iv Neighboring-Group Assistance in Free-Radical Reactions
  • 14.B Reactivity
  • 14.B.i Reactivity for Aliphatic Substrates
  • 14.B.ii Reactivity at a Bridgehead
  • 14.B.iii Reactivity in Aromatic Substrates
  • 14.B.iv Reactivity in the Attacking Radical
  • 14.B.v The Effect of Solvent on Reactivity
  • 14.C Reactions
  • 14.C.i Hydrogen as Leaving Group
  • 14.C.ii N2 as Leaving Group
  • 14.C.iii Metals as Leaving Groups
  • 14.C.iv Halogen as Leaving Group
  • 14.C.v Sulfur as Leaving Group
  • 14.C.vi Carbon as Leaving Group
  • 15 Addition to Carbon-Carbon Multiple Bonds
  • 15.A Mechanisms
  • 15.A.i Electrophilic Addition
  • 15.A.ii Nucleophilic Addition
  • 15.A.iii Free-Radical Addition
  • 15.A.iv Cyclic Mechanisms
  • 15.B Orientation And Reactivity
  • 15.B.i Reactivity
  • 15.B.ii Orientation
  • 15.B.iii Stereochemical Orientation
  • 15.B.iv Addition to Cyclopropane Rings
  • 15.C Reactions
  • 15.C.i Isomerization Of Double And Triple Bonds
  • 15.C.ii Reactions In Which Hydrogen Adds To One Side
  • 15.C.ii Reactions In Which Hydrogen Adds To Neither Side
  • 15.C.iii Cycloaddition Reactions
  • C16 Addition to Carbon-Hetero Multiple Bonds
  • 16.A Mechanism and Reactivity
  • 16.A.i Nucleophilic Substitution at an Aliphatic Trigonal Carbon. The Tetrahedral Mechanism
  • 16.B Reactions
  • 16.B.i Reactions In Which Hydrogen Or A Metallic Ion Adds To The Heteroatom
  • 16.B.ii Acyl Substitution Reactions
  • 16.B.iii Reactions In Which Carbon Adds To The Heteroatom
  • 16.B.iv Addition To Isocyanides
  • 16.B.v Nucleophilic Substitution At A Sulfonyl Sulfur Atom
  • Chapter 17 Eliminations
  • 17.A Mechanisms and Orientation
  • 17.A.i The E2 Mechanism
  • 17.A.ii The E1 Mechanism
  • 17.A.iii The E1cB Mechanism
  • 17.A.iv The E1-E2-E1cB Spectrum
  • 17.A.v The E2C Mechanism
  • 17.B Regiochemistry of the Double Bond
  • 17.C Stereochemistry of the Double Bond
  • 17.D Reactivity
  • 17.D.i Effect of Substrate Structure
  • 17.D.ii Effect of the Attacking Base
  • 17.D.iii Effect of the Leaving Group
  • 17.D.iv Effect of the Medium
  • 17.E Mechanisms and Orientation in Pyrolytic Eliminations
  • 17.E.i Mechanisms
  • 17.E.ii Orientation in Pyrolytic Eliminations
  • 17.E.iii 1,4 Conjugate Eliminations
  • 17.F Reactions
  • 17.F.i Reactions In Which C=C And C?C Bonds Are Formed
  • 17.F.ii Fragmentations
  • 17.F.iii Reactions In Which C?N Or C=N Bonds Are Formed
  • 17.F.iv Reactions In Which C=O Bonds Are Formed
  • 17.F.v Reactions In Which N=N Bonds Are Formed
  • 17.F.vi Extrusion Reactions
  • Chapter 18 Rearrangements
  • 18.A Mechanisms
  • 18.A.i Nucleophilic Rearrangements
  • 18.A.ii The Actual Nature of the Migration
  • 18.A.iii Migratory Aptitudes
  • 18.A.iv Memory Effects
  • 18.B Longer Nucleophilic Rearrangements
  • 18.C Free-Radical Rearrangements
  • 18.D Carbene Rearrangements
  • 18.E Electrophilic Rearrangements
  • 18.F Reactions
  • 18.F.i 1,2-Rearrangements
  • 18.F.ii Non-1,2 Rearrangements
  • Chapter 19 Oxidations and Reductions
  • 19.A Mechanisms
  • 19.B Reactions
  • 19.B.i Oxidations
  • 19.B.ii Reductions
  • Appendix A The Literature of Organic Chemistry
  • A Primary Sources
  • A.i Journals
  • A.ii Patents
  • B Secondary Sources
  • B.i Listings of Titles
  • B.ii Abstracts
  • B.iii Beilstein
  • B.iv Tables of Information
  • C Reviews
  • C.i Annual Reviews
  • C.ii Awareness Services
  • C.iii General Treatises
  • C.iv Monographs and Treatises on Specific Areas
  • C.v Textbooks
  • C.vi Other Books
  • D Literature Searching
  • D.i Literature Searching Using Printed Materials
  • D.ii Literature Searching Online
  • D.iii Sci-Finder - the CAS database
  • D.iv Science Citation Index
  • D.v How to Locate Journal Articles
  • D.vi Reaxys
  • Appendix B Classification of Reactions by Type of Compounds Synthesized
  • Author Index
  • Index

Author notes provided by Syndetics

MICHAEL B. SMITH, PhD, is Professor in the Department of Chemistry at the University of Connecticut. He is a coauthor of the fifth and sixth editions of March's Advanced Organic Chemistry and the author of Volumes 6 - 12 of the Compendium of Organic Synthetic Methods (Wiley) as well as several other monographs.

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