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MARCH'S ADVANCED ORGANIC CHEMISTRY

REACTIONS, MECHANISMS, AND STRUCTURE

9781119371809 ::  MARCH'S ADVANCED ORGANIC CHEMISTRY
ISBN:

9781119371809

EditorialJOHN WILEY & SONS LTD.
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Pàgines:2144
Idioma:INGLES
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NEW REACTION SECTIONS CORRELATION: 7TH EDITION 8TH EDITION XVPREFACE XXICOMMON ABBREVIATIONS XXVBIOGRAPHICAL STATEMENT XXXINEW FEATURES OF THE 8TH EDITION XXXIIIPART I INTRODUCTION 11. LOCALIZED CHEMICAL BONDING 31.A. COVALENT BONDING 31.B. MULTIPLE VALENCE 71.C. HYBRIDIZATION 71.D. MULTIPLE BONDS 91.E. PHOTOELECTRON SPECTROSCOPY 121.F. ELECTRONIC STRUCTURES OF MOLECULES 151.G. ELECTRONEGATIVITY 171.H. DIPOLE MOMENT 191.I. INDUCTIVE AND FIELD EFFECTS 201.J. BOND DISTANCES 231.K. BOND ANGLES 271.L. BOND ENERGIES 292. DELOCALIZED CHEMICAL BONDING 332.A. MOLECULAR ORBITALS 342.B. BOND ENERGIES AND DISTANCES IN COMPOUNDS CONTAINING DELOCALIZED BONDS 372.C. MOLECULES THAT HAVE DELOCALIZED BONDS 392.D. CROSS CONJUGATION 442.E. THE RULES OF RESONANCE 462.F. THE RESONANCE EFFECT 482.G. STERIC INHIBITION OF RESONANCE AND THE INFLUENCES OF STRAIN 482.H. P -D BONDING: YLIDS 522.I. AROMATICITY 542.I.I. SIX-MEMBERED RINGS 582.I.II. FIVE-, SEVEN-, AND EIGHT-MEMBERED RINGS 622.I.III. OTHER SYSTEMS CONTAINING AROMATIC SEXTETS 672.J. ALTERNANT AND NONALTERNANT HYDROCARBONS 682.K. AROMATIC SYSTEMS WITH ELECTRON NUMBERS OTHER THAN SIX 702.K.I. SYSTEMS OF TWO ELECTRONS 722.K.II. SYSTEMS OF FOUR ELECTRONS: ANTIAROMATICITY 732.K.III. SYSTEMS OF EIGHT ELECTRONS 762.K.IV. SYSTEMS OF TEN ELECTRONS 772.K.V. SYSTEMS OF MORE THAN TEN ELECTRONS: 4N + 2 ELECTRONS 802.K.VI. SYSTEMS OF MORE THAN TEN ELECTRONS: 4N ELECTRONS 852.L. OTHER AROMATIC COMPOUNDS 892.M. HYPERCONJUGATION 922.N. TAUTOMERISM 962.N.I. KETO-ENOL TAUTOMERISM 972.N.II. OTHER PROTON-SHIFT TAUTOMERISM 1003. BONDING WEAKER THAN COVALENT 1053.A. HYDROGEN BONDING 1053.B. - INTERACTIONS 1133.C. ADDITION COMPOUNDS 1143.C.I. ELECTRON DONOR-ACCEPTOR (EDA) COMPLEXES 1143.C.II. CROWN ETHER COMPLEXES AND CRYPTATES 1173.C.III. INCLUSION COMPOUNDS 1223.C.IV. CYCLODEXTRINS 1253.D. CATENANES AND ROTAXANES 1273.E. CUCURBIT[N]URIL-BASED GYROSCANE 1314. STEREOCHEMISTRY AND CONFORMATION 1334.A. OPTICAL ACTIVITY AND CHIRALITY 1334.B. DEPENDENCE OF ROTATION ON CONDITIONS OF MEASUREMENT 1354.C. WHAT KINDS OF MOLECULES DISPLAY OPTICAL ACTIVITY? 1364.D. THE FISCHER PROJECTION 1474.E. ABSOLUTE CONFIGURATION 1484.E.I. THE CAHN-INGOLD-PRELOG SYSTEM 1504.E.II. METHODS OF DETERMINING CONFIGURATION 1524.F. THE CAUSE OF OPTICAL ACTIVITY 1564.G. MOLECULES WITH MORE THAN ONE STEREOGENIC CENTER 1574.H. ASYMMETRIC SYNTHESIS 1614.I. METHODS OF RESOLUTION 1664.J. OPTICAL PURITY 1734.K. CIS-TRANS ISOMERISM 1754.K.I. CIS-TRANS ISOMERISM RESULTING FROM DOUBLE BONDS 1754.K.II. CIS-TRANS ISOMERISM OF MONOCYCLIC COMPOUNDS 1794.K.III. CIS-TRANS ISOMERISM OF FUSED AND BRIDGED RING SYSTEMS 1804.L. OUT-IN ISOMERISM 1814.M. ENANTIOTOPIC AND DIASTEREOTOPIC ATOMS, GROUPS, AND FACES 1834.N. STEREOSPECIFIC AND STEREOSELECTIVE SYNTHESES 1864.O. CONFORMATIONAL ANALYSIS 1874.O.I. CONFORMATION IN OPEN-CHAIN SYSTEMS 1884.O.II. CONFORMATION IN SIX-MEMBERED RINGS 1944.O.III. CONFORMATION IN SIX-MEMBERED RINGS CONTAINING HETEROATOMS 1994.O.IV. CONFORMATION IN OTHER RINGS 2024.P. MOLECULAR MECHANICS 2044.Q. STRAIN 2064.Q.I. STRAIN IN SMALL RINGS 2074.Q.II. STRAIN IN OTHER RINGS 2134.Q.III. UNSATURATED RINGS 2154.Q.IV. STRAIN DUE TO UNAVOIDABLE CROWDING 2185. CARBOCATIONS, CARBANIONS, FREE RADICALS, CARBENES, AND NITRENES 2235.A. CARBOCATIONS 2245.A.I. NOMENCLATURE 2245.A.II. STABILITY AND STRUCTURE OF CARBOCATIONS 2245.A.III. THE GENERATION AND FATE OF CARBOCATIONS 2345.B. CARBANIONS 2375.B.I. STABILITY AND STRUCTURE 2375.B.II. THE STRUCTURE OF ORGANOMETALLIC COMPOUNDS 2445.B.III. THE GENERATION AND FATE OF CARBANIONS 2495.C. FREE RADICALS 2505.C.I. STABILITY AND STRUCTURE 2505.C.II. THE GENERATION AND FATE OF FREE RADICALS 2615.C.III. RADICAL IONS 2655.D. CARBENES 2665.D.I. STABILITY AND STRUCTURE 2665.D.II. THE GENERATION AND FATE OF CARBENES 2695.D.III. N-HETEROCYCLIC CARBENES (NHCS) 2745.E. NITRENES 2766. MECHANISMS AND METHODS OF DETERMINING THEM 2796.A. TYPES OF MECHANISM 2796.B. TYPES OF REACTION 2806.C. THERMODYNAMIC REQUIREMENTS FOR REACTION 2836.D. KINETIC REQUIREMENTS FOR REACTION 2846.E. THE BALDWIN RULES FOR RING CLOSURE 2886.F. KINETIC AND THERMODYNAMIC CONTROL 2906.G. THE HAMMOND POSTULATE 2916.H. MICROSCOPIC REVERSIBILITY 2916.I. MARCUS THEORY 2926.J. METHODS OF DETERMINING MECHANISMS 2936.J.I. IDENTIFICATION OF PRODUCTS 2936.J.II. DETERMINATION OF THE PRESENCE OF AN INTERMEDIATE 2946.J.III. THE STUDY OF CATALYSIS 2956.J.IV. ISOTOPIC LABELING 2966.J.V. STEREOCHEMICAL EVIDENCE 2966.J.VI. KINETIC EVIDENCE 2976.J.VII. ISOTOPE EFFECTS 3046.K. CATALYST DEVELOPMENT 3087. IRRADIATION PROCESSES AND TECHNIQUES THAT INFLUENCE REACTIONS IN ORGANIC CHEMISTRY 3137.A. PHOTOCHEMISTRY 3147.A.I. EXCITED STATES AND THE GROUND STATE 3147.A.II. SINGLET AND TRIPLET STATES: "FORBIDDEN" TRANSITIONS 3167.A.III. TYPES OF EXCITATION 3177.A.IV. NOMENCLATURE AND PROPERTIES OF EXCITED STATES 3187.A.V. PHOTOLYTIC CLEAVAGE 3197.A.VI. THE FATE OF THE EXCITED MOLECULE: PHYSICAL PROCESSES 3207.A.VII. THE FATE OF THE EXCITED MOLECULE: CHEMICAL PROCESSES 3257.A.VIII. THE DETERMINATION OF PHOTOCHEMICAL MECHANISMS 3307.B. SONOCHEMISTRY 3317.C. MICROWAVE CHEMISTRY 3347.D. FLOW CHEMISTRY 3367.E. MECHANOCHEMISTRY 3388. ACIDS AND BASES 3398.A. BRONSTED THEORY 3398.A.I. BRONSTED ACIDS 3408.A.II. BRONSTED BASES 3478.B. THE MECHANISM OF PROTON TRANSFER REACTIONS 3508.C. MEASUREMENTS OF SOLVENT ACIDITY 3528.D. ACID AND BASE CATALYSIS 3558.E. LEWIS ACIDS AND BASES 3578.E.I. HARD-SOFT ACIDS-BASES 3598.F. THE EFFECTS OF STRUCTURE ON THE STRENGTHS OF ACIDS AND BASES 3618.G. THE EFFECTS OF THE MEDIUM ON ACID AND BASE STRENGTH 3709. EFFECTS OF STRUCTURE AND MEDIUM ON REACTIVITY 3759.A. RESONANCE AND FIELD EFFECTS 3759.B. STERIC EFFECTS 3779.C. QUANTITATIVE TREATMENTS OF THE EFFECT OF STRUCTURE ON REACTIVITY 3809.D. EFFECT OF MEDIUM ON REACTIVITY AND RATE 3909.E. HIGH PRESSURE 3909.F. WATER AND OTHER NONORGANIC SOLVENTS 3919.G. IONIC LIQUID SOLVENTS 3939.H. SOLVENTLESS REACTIONS 395PART II INTRODUCTION 39710. ALIPHATIC SUBSTITUTION, NUCLEOPHILIC AND ORGANOMETALLIC 40310.A. MECHANISMS 40410.A.I. THE SN2 MECHANISM 40410.A.II. THE SN1 MECHANISM 41010.A.III. ION PAIRS IN THE SN1 MECHANISM 41410.A.IV. MIXED SN1 AND SN2 MECHANISMS 41810.B. SET MECHANISMS 42010.C. THE NEIGHBORING-GROUP MECHANISM 42210.C.I. NEIGHBORING-GROUP PARTICIPATION BY AND BONDS: NONCLASSICAL CARBOCATIONS 42510.D. THE SNI MECHANISM 44010.E. NUCLEOPHILIC SUBSTITUTION AT AN ALLYLIC CARBON: ALLYLIC REARRANGEMENTS 44110.F. NUCLEOPHILIC SUBSTITUTION AT AN ALIPHATIC TRIGONAL CARBON: THE TETRAHEDRAL MECHANISM 44510.G. REACTIVITY 44910.G.I. THE EFFECT OF SUBSTRATE STRUCTURE 44910.G.II. THE EFFECT OF THE ATTACKING NUCLEOPHILE 45710.G.III. THE EFFECT OF THE LEAVING GROUP 46410.G.IV. THE EFFECT OF THE REACTION MEDIUM 46910.G.V. PHASE-TRANSFER CATALYSIS 47410.G.VI. INFLUENCING REACTIVITY BY EXTERNAL MEANS 47710.G.VII. AMBIDENT (BIDENTANT) NUCLEOPHILES: REGIOSELECTIVITY 47810.G.VIII. AMBIDENT SUBSTRATES 48110.H. REACTIONS 48310.H.I. OXYGEN NUCLEOPHILES 48310.H.II. SULFUR NUCLEOPHILES 50610.H.III. NITROGEN NUCLEOPHILES 51210.H.IV. HALOGEN NUCLEOPHILES 53410.H.V. CARBON NUCLEOPHILES 54511. AROMATIC SUBSTITUTION, ELECTROPHILIC 60711.A. MECHANISMS 60711.A.I. THE ARENIUM ION MECHANISM 60811.A.II. THE SE1 MECHANISM 61311.B. ORIENTATION AND REACTIVITY 61411.B.I. ORIENTATION AND REACTIVITY IN MONOSUBSTITUTED BENZENE RINGS 61411.B.II. THE ORTHO/PARA RATIO 61811.B.III. IPSO ATTACK 62011.B.IV. ORIENTATION IN BENZENE RINGS WITH MORE THAN ONE SUBSTITUENT 62111.B.V. ORIENTATION IN OTHER RING SYSTEMS 62211.C. QUANTITATIVE TREATMENTS OF REACTIVITY IN THE SUBSTRATE 62411.D. A QUANTITATIVE TREATMENT OF REACTIVITY OF THE ELECTROPHILE: THE SELECTIVITY RELATIONSHIP 62611.E. THE EFFECT OF THE LEAVING GROUP 62811.F. REACTIONS 62911.F.I. HYDROGEN AS THE LEAVING GROUP IN SIMPLE SUBSTITUTION REACTIONS 62911.F.II. HYDROGEN AS THE LEAVING GROUP IN REARRANGEMENT REACTIONS 67511.F.III. OTHER LEAVING GROUPS 68012. ALIPHATIC, ALKENYL, AND ALKYNYL SUBSTITUTION: ELECTROPHILIC AND ORGANOMETALLIC 68712.A. MECHANISMS 68712.A.I. BIMOLECULAR MECHANISMS. SE2 AND SEI 68812.A.II. THE SE1 MECHANISM 69112.A.III. ELECTROPHILIC SUBSTITUTION ACCOMPANIED BY DOUBLE-BOND SHIFTS 69412.A.IV. OTHER MECHANISMS 69512.B. REACTIVITY 69512.C. REACTIONS 69712.C.I. HYDROGEN AS LEAVING GROUP 69712.C.II. METALS AS LEAVING GROUPS 73312.C.III. HALOGEN AS LEAVING GROUP 74612.C.IV. CARBON LEAVING GROUPS 75112.C.V. ELECTROPHILIC SUBSTITUTION AT NITROGEN 76013. AROMATIC SUBSTITUTION: NUCLEOPHILIC AND ORGANOMETALLIC 76713.A. MECHANISMS 76813.A.I. THE SNAR MECHANISM 76813.A.II. THE SN1 MECHANISM 77113.A.III. THE BENZYNE MECHANISM 77213.A.IV. THE SRN1 MECHANISM 77413.A.V. OTHER MECHANISMS 77613.B. REACTIVITY 77613.B.I. THE EFFECT OF SUBSTRATE STRUCTURE 77613.B.II. THE EFFECT OF THE LEAVING GROUP 77813.B.III. THE EFFECT OF THE ATTACKING NUCLEOPHILE 77913.C. REACTIONS 77913.C.I. ALL LEAVING GROUPS EXCEPT HYDROGEN AND N2+ 77913.C.II. HYDROGEN AS LEAVING GROUP 82313.C.III. NITROGEN AS LEAVING GROUP 82413.C.IV. REARRANGEMENTS 83414. RADICAL REACTIONS 83914.A. MECHANISMS 83914.A.I. RADICAL MECHANISMS IN GENERAL 83914.A.II. FREE-RADICAL SUBSTITUTION MECHANISMS 84414.A.III. MECHANISMS AT AN AROMATIC SUBSTRATE 84514.A.IV. NEIGHBORING-GROUP ASSISTANCE IN FREE-RADICAL REACTIONS 84714.B. REACTIVITY 84814.B.I. REACTIVITY FOR ALIPHATIC SUBSTRATES 84814.B.II. REACTIVITY AT A BRIDGEHEAD 85314.B.III. REACTIVITY IN AROMATIC SUBSTRATES 85414.B.IV. REACTIVITY IN THE ATTACKING RADICAL 85514.B.V. THE EFFECT OF SOLVENT ON REACTIVITY 85614.C. REACTIONS 85614.C.I. HYDROGEN AS LEAVING GROUP 85614.C.II. METALS AS LEAVING GROUPS 88014.C.III. HALOGEN AS LEAVING GROUP 88314.C.IV. SULFUR AS LEAVING GROUP 88314.C.V. CARBON AS LEAVING GROUP 88515. ADDITION TO CARBON-CARBON MULTIPLE BONDS 89115.A. MECHANISMS 89215.A.I. ELECTROPHILIC ADDITION 89215.A.II. NUCLEOPHILIC ADDITION 89515.A.III. FREE-RADICAL ADDITION 89615.A.IV. CYCLIC MECHANISMS 89815.A.V. ADDITION TO CONJUGATED SYSTEMS 89815.B. ORIENTATION AND REACTIVITY 89915.B.I. REACTIVITY 89915.B.II. ORIENTATION 90215.B.III. STEREOCHEMICAL ORIENTATION 90415.B.IV. ADDITION TO CYCLOPROPANE RINGS 90615.C. REACTIONS 90815.C.I. ISOMERIZATION OF DOUBLE AND TRIPLE BONDS 90815.C.II. REACTIONS IN WHICH HYDROGEN ADDS TO ONE SIDE 91015.C.III. REACTIONS IN WHICH HYDROGEN ADDS TO NEITHER SIDE 99215.C.IV. CYCLOADDITION REACTIONS 102716. ADDITION TO CARBON-HETEROATOM MULTIPLE BONDS 108716.A. MECHANISM AND REACTIVITY 108716.A.I. NUCLEOPHILIC SUBSTITUTION AT AN ALIPHATIC TRIGONAL CARBON: THE TETRAHEDRAL MECHANISM 108916.B. REACTIONS 109416.B.I. REACTIONS IN WHICH HYDROGEN OR A METALLIC ION ADDS TO THE HETEROATOM 109516.B.II. ACYL SUBSTITUTION REACTIONS 121816.B.III. REACTIONS IN WHICH CARBON ADDS TO THE HETEROATOM 125716.B.IV. ADDITION TO ISOCYANIDES 126416.B.V. NUCLEOPHILIC SUBSTITUTION AT A SULFONYL SULFUR ATOM 126617. ELIMINATION REACTIONS 127317.A. MECHANISMS AND ORIENTATION 127317.A.I. THE E2 MECHANISM 127417.A.II. THE E1 MECHANISM 128017.A.III. THE E1CB MECHANISM 128117.A.IV. THE E1-E2-E1CB SPECTRUM 128617.A.V. THE E2C MECHANISM 128717.B. REGIOCHEMISTRY OF THE DOUBLE BOND 128817.C. STEREOCHEMISTRY OF THE DOUBLE BOND 129017.D. REACTIVITY 129117.D.I. EFFECT OF SUBSTRATE STRUCTURE 129117.D.II. EFFECT OF THE ATTACKING BASE 129317.D.III. EFFECT OF THE LEAVING GROUP 129417.D.IV. EFFECT OF THE MEDIUM 129417.E. MECHANISMS AND ORIENTATION IN PYROLYTIC ELIMINATIONS 129517.E.I. MECHANISMS 129517.E.II. ORIENTATION IN PYROLYTIC ELIMINATIONS 129817.E.III. 1,4 CONJUGATE ELIMINATIONS 129817.F. REACTIONS 129917.F.I. REACTIONS IN WHICH C C AND C C BONDS ARE FORMED 129917.F.II. FRAGMENTATIONS 132117.F.III. REACTIONS IN WHICH C N OR C N BONDS ARE FORMED 132517.F.IV. REACTIONS IN WHICH C O BONDS ARE FORMED 132817.F.V. REACTIONS IN WHICH N N BONDS ARE FORMED 132917.F.VI. EXTRUSION REACTIONS 132918. REARRANGEMENTS 133518.A. MECHANISMS 133618.A.I. NUCLEOPHILIC REARRANGEMENTS 133618.A.II. THE ACTUAL NATURE OF THE MIGRATION 133718.A.III. MIGRATORY APTITUDES 134018.A.IV. MEMORY EFFECTS 134318.B. LONGER NUCLEOPHILIC REARRANGEMENTS 134418.C. FREE-RADICAL REARRANGEMENTS 134518.D. CARBENE REARRANGEMENTS 134918.E. ELECTROPHILIC REARRANGEMENTS 134918.F. REACTIONS 135018.F.I. 1,2-REARRANGEMENTS 135018.F.II. NON 1,2-REARRANGEMENTS 138919. OXIDATIONS AND REDUCTIONS 143919.A. MECHANISMS 144019.B. REACTIONS 144219.B.I. OXIDATIONS 144219.B.II. REDUCTIONS 1510APPENDIX A: THE LITERATURE OF ORGANIC CHEMISTRY 1607APPENDIX B: CLASSIFICATION OF REACTIONS BY TYPE OF COMPOUNDS SYNTHESIZED 1645INDEXESAUTHOR INDEX 1669SUBJECT INDEX 1917

THE COMPLETELY REVISED AND UPDATED, DEFINITIVE RESOURCE FOR STUDENTS AND PROFESSIONALS IN ORGANIC CHEMISTRY THE REVISED AND UPDATED 8TH EDITION OF MARCH'S ADVANCED ORGANIC CHEMISTRY: REACTIONS, MECHANISMS, AND STRUCTURE EXPLAINS THE THEORIES OF ORGANIC CHEMISTRY WITH EXAMPLES AND REACTIONS. THIS BOOK IS THE MOST COMPREHENSIVE RESOURCE ABOUT ORGANIC CHEMISTRY AVAILABLE. READERS ARE GUIDED ON THE PLANNING AND EXECUTION OF MULTI-STEP SYNTHETIC REACTIONS, WITH DETAILED DESCRIPTIONS OF ALL THE REACTIONS THE OPENING CHAPTERS OF MARCH'S ADVANCED ORGANIC CHEMISTRY, 8TH EDITION DEAL WITH THE STRUCTURE OF ORGANIC COMPOUNDS AND DISCUSS IMPORTANT ORGANIC CHEMISTRY BONDS, FUNDAMENTAL PRINCIPLES OF CONFORMATION, AND STEREOCHEMISTRY OF ORGANIC MOLECULES, AND REACTIVE INTERMEDIATES IN ORGANIC CHEMISTRY. FURTHER COVERAGE CONCERNS GENERAL PRINCIPLES OF MECHANISM IN ORGANIC CHEMISTRY, INCLUDING ACIDS AND BASES, PHOTOCHEMISTRY, SONOCHEMISTRY AND MICROWAVE IRRADIATION. THE RELATIONSHIP BETWEEN STRUCTURE AND REACTIVITY IS ALSO COVERED. THE FINAL CHAPTERS COVER THE NATURE AND SCOPE OF ORGANIC REACTIONS AND THEIR MECHANISMS.

THIS EDITION: PROVIDES REVISED EXAMPLES AND CITATIONS THAT REFLECT ADVANCES IN AREAS OF ORGANIC CHEMISTRY PUBLISHED BETWEEN 2011 AND 2017INCLUDES APPENDICES ON THE LITERATURE OF ORGANIC CHEMISTRY AND THE CLASSIFICATION OF REACTIONS ACCORDING TO THE COMPOUNDS PREPAREDINSTRUCTS THE READER ON PREPARING AND CONDUCTING MULTI-STEP SYNTHETIC REACTIONS, AND PROVIDES COMPLETE DESCRIPTIONS OF EACH REACTION THE 8TH EDITION OF MARCH'S ADVANCED ORGANIC CHEMISTRY PROVES ONCE AGAIN THAT IT IS A MUST-HAVE DESKTOP REFERENCE AND TEXTBOOK FOR EVERY STUDENT AND PROFESSIONAL WORKING IN ORGANIC CHEMISTRY OR RELATED FIELDS.

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