March's Advanced Organic Chemistry
John Wiley & Sons Inc (Hersteller)
978-1-118-47979-7 (ISBN)
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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.
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 1K. BOND ANGLES 1.L. BOND ENERGIES CHAPTER TWO 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. pPI-dPI 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. THE 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. RADICAL 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 PI 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
| Erscheint lt. Verlag | 12.4.2013 |
|---|---|
| Verlagsort | New York |
| Sprache | englisch |
| Maße | 95 x 215 mm |
| Gewicht | 14 g |
| Themenwelt | Naturwissenschaften ► Chemie ► Organische Chemie |
| ISBN-10 | 1-118-47979-3 / 1118479793 |
| ISBN-13 | 978-1-118-47979-7 / 9781118479797 |
| Zustand | Neuware |
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