Holdings: March's advanced organic chemistry

March's advanced organic chemistry: reactions, mechanisms, and structure

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Bibliographic Details
Previous Title:	March, Jerry Advanced organic chemistry
Main Author:	Smith, Michael B. 1946- (Author)
Format:	Book
Language:	English
Published:	Hoboken, NJ Wiley 2013
Edition:	7th ed.
Subjects:	Organische Chemie Reaktionsmechanismus Reaktivität Chemischer Prozess Chemische Struktur Chemische Reaktion Chemische Bindung Lehrbuch
Online Access:	Inhaltsverzeichnis
Physical Description:	XXV, 2047 S. Ill., graph. Darst.
ISBN:	9780470462591

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Record in the Search Index

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adam_text	CONTENTS PREFACE xiii COMMON ABBREVIATIONS xxi BIOGRAPHICAL STATEMENT xxv PART I INTRODUCTION 1 1. Localized Chemical Bonding 3 I.A. CovalentBonding 3 l.B. Multiple Valence 6 l.C. Hybridization 7 I.D. Multiple Bonds 9 1 .E. Photoelectron Spectroscopy 11 l.F. Electronic Structures of Molecules 14 l.G. Electronegativity 15 l.H. Dipole Moment 18 1.1. Inductive and Field Effects 19 l.J. Bond Distances 21 l.K. Bond Angles 25 l.L. Bond Energies 27 2. Delocalized Chemical Bonding 31 2.A. Molecular Orbitals 32 2.B. Bond Energies and Distances in Compounds Containing Delocalized Bonds 35 2.C. Molecules that have Delocalized Bonds 37 2.D. Cross-Conjugation 42 2.E. The Rules of Resonance 43 2.F. The Resonance Effect 45 2.G. Steric Inhibition of Resonance and the Influences of Strain 46 2.H. ρπ-ώτ Bonding. Ylids 49 2.1. Aromaticity 50 2.І.І. Six-Membered Rings 54 2.I.Ü. Five, Seven, and Eight-Membered Rings 57 2.1-üi. Other Systems Containing Aromatic Sextets 62 2 J. Alternant and Nonalteraant Hydrocarbons 63 VÍ CONTENTS 2. К. Aromatic Systems with Electron Numbers other than Six 65 2.К.І. Systems of Two Electrons 66 2.K.Ü. Systems of Four Electrons: Antiaromaticity 67 2.К.ІІІ. Systems of Eight Electrons 71 2.K.1V. Systems of Ten Electrons 72 2.K.V. Systems of more than Ten Electrons: An + 2 Electrons 74 2.K.VÌ. Systems of more than 10 Electrons: 4n Electrons 79 2.L. Other Aromatic Compounds 82 2.M. Hyperconjugation 85 2.N. Tautomerism 89 2.N.Ì. Ket o-Enol Tautomerism 89 2.N.11. Other Proton-Shift Tautomensm 92 3. Bonding Weaker Than Covalent 96 3.A. Hydrogen Bonding 96 3.B. π -лг Interactions 103 3.C. Addition Compounds 104 З.С.і. Electron Donor-Acceptor Complexes 104 З.С.іі. Crown Ether Complexes and Cryptâtes 108 З.С.ііі. Inclusion Compounds 113 3.C.1V. Cyclodextrins 116 3.D. Catenaries and Rotaxanes 118 3.E. CucurbitfwJUril-Based Gyroscane 121 4. Stereochemistry and Conformation 122 4. A. Optical Activity and Chirality 122 4. Ал. Dependence of Rotation on Conditions of Measurement 124 4.B. What Kinds of Molecules Display Optical Activity7 125 4. С The Fischer Projection 136 4.D. Absolute Configuration 137 4.D.I. The CAHN-INGOLD-PRELOG System 138 4.D.Ü. Methods of Determining Configuration 141 4.E. The Cause of Optical Activity 145 4.F. Molecules with more than One Stereogemc Center 146 4.G. Asymmetric Synthesis 149 4.H. Methods of Resolution 154 4.1. Optical Punty 160 4.1. cis-trans Isomerism 162 4.J.Ì. cis-trans Isomensm Resulting from Double Bonds 162 4.J.Ü. cis-trans Isomensm of Monocyclic Compounds 165 4.1.111. cis-trans Isomensm of Fused and Bridged Ring Systems 167 4.K. Out-In Isomensm 168 4.L. Enantiotopic and Diastereotopic Atoms, Groups, and Faces 170 4.M. Stereospecific and Stereoselective Syntheses 173 4.N. Conformational Analysis 173 4.N.I. Conformation in Open-Cham Systems 175 CONTENTS VII 4.N.Ü. Conformation in Six -Membered Rings 180 4.N.ÜÍ. Conformation in Six-Membered Rings Containing Heteroatoms 186 4.N.1V. Conformation in Other Rings 188 4.0. Molecular Mechanics 190 4.P. STRAIN ] 92 4. P.i. Strain m Small Rings 193 4.P.Ü. Strain in Other Rings 199 4.P.ÜÍ. Unsaturated Rings 201 4.P.1V. Strain Due to Unavoidable Crowding 204 5. Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes 208 5.A. Carbocations 208 S.A.r Nomenclature 208 5. A.u. Stability and Structure of Carbocations 209 5. А.пі. The Generation and Fate of Carbocations 218 5.B. Carbanions 221 5.В.1. Stability and Structure 221 5.B.Ü. The Structure of Organometallic Compounds 228 5.В.ІІІ. The Generation and Fate of Carbanions 233 5. С Free Radicals 234 5. C.i. Stability and Structure 234 5.C.Ü. The Generation and Fate of Free Radicals 245 5. Ciii. Radical Ions 248 5.D. Carbenes 249 5.D.i. Stability and Structure 249 5.D.U. The Generation and Fate of Carbenes 253 5.E. Nitrenes 257 6. Mechanisms and Methods of Determining them 261 6. A. Types of Mechanism 261 6.B. Types of Reaction 262 6.C. Thermodynamic Requirements for Reaction 264 6.D. Kinetic Requirements for Reaction 266 6.E. The Baldwin Rules for Ring Closure 270 6.F. Kinetic and Thermodynainic Control 271 6.G. The Hammond Postulate 272 6.H. Microscopic Reversibility 273 6.1. Marcus Theory 273 6.J. Methods of Determining Mechanisms 275 6. J.i. Identification of Products 275 6.J.11. Determination of the Presence of an Intermediate 275 6.Ј.Ш. The Study of Catalysis 277 6J.iv. Isotopie Labeimg 277 6.J.V. Stereochemical Evidence 278 6 J.vi. Kinetic Evidence 278 6 J.vii. Isotope Effects 285 VÍM CONTENTS 7. Irradiation Processes in Organic Chemistry 289 7. Λ. Photochemistry 289 7. А.і. Excited States and the Ground State 289 7.A.Ü. Singlet and Triplet States: Forbidden Transitions 291 7. A.iii. Types of Excitation 292 7. A. iv. Nomenclature and Properties of Excited States 294 7.A.V. Photolytic Cleavage 295 7. A. vi. The Fate of the Excited Molecule: Physical Processes 296 7. A.vii. The Fate of the Excited Molecule: Chemical Processes 301 7. A. viii. The Determination of Photochemical Mechanisms 306 7.B. Sonochemistry 307 7.C. Microwave Chemistry 309 8. Acids and Bases 312 8. A. Br0nsted Theory 312 8. A.i. Br0nsted Acids 313 8. А.п. Br0nsted Bases 320 8.B. The Mechanism of Proton-Transfer Reactions 323 8.C. Measurements of Solvent Acidity 324 8.D. Acid and Base Catalysis 327 8.E. Lewis Acids and Bases 330 8.Е.1. Hard-Soft Acids-Bases 331 8.F. The Effects of Structure on the Strengths of Acids and Bases 334 8.G. The Effects of the Medium on Acid and Base Strength 343 9. Effects of Structure and Medium on Reactivity 347 9. A. Resonance and Field Effects 347 9.B. Stenc Effects 349 9. С Quantitative Treatments of the Effect of Structure on Reactivity 352 9.D. Effect of Medium on Reactivity and Rate 361 9.D.I. Hrgh Pressure 362 9.D.Ü. Water and Other Non-Organic Solvents 363 9.D.111. Ionic Solvents 364 9.D.ÌV. Solventless Reactions 366 PART II INTRODUCTION 367 10. Aliphatic Substitution, Nucleophilic and Organometallic 373 1 O.A. Mechanisms 373 lO.A.i. The SN2 Mechanism 374 lO.A.ii. The SN1 Mechanism 379 lO.A.iii. Ion Pairs in the SN1 Mechanism 383 lO.A.iv. Mixed SN1 and SN2 Mechanisms 387 10.B. SET Mechanisms 389 CONTENTS ¡X 10. С. The Neighboring-Group Mechanism 391 10. C.i. Neighboring-Group Participation by π and σ Bonds: Nonclassical Carbocaüons 394 10.D. The SNi Mechanism 408 10. E. Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements 409 10. F. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 413 10. G. Reactivity 417 lO.G.i. The Effect of Substrate Structure 417 lO.G.ii. The Effect of the Attacking Nucleophile 426 10. G. iii. The Effect of the Leaving Group 432 lO.G.iv. The Effect of the Reaction Medium 435 lO.G.v. Phase-Transfer Catalysis 442 lO.G.vi. Influencing Reactivity by External Means 445 10. G. vii. Ambident (Bidentant) Nucleophiles: Regioselectivity 446 lO.G.viii. Ambident Substrates 450 10.H. Reactions 451 10.Н.І. Oxygen Nucleophiles 451 lO.H.ii. Attack by OR at an Alkyl Carbon 459 10. H. iii. Sulfur Nucleophiles 475 lO.H.iv. Nitrogen Nucleophiles 481 lO.H.v. Halogen Nucleophiles 498 lO.H.vi. Carbon Nucleophiles 510 11. Aromatic Substitution, Electrophilic 569 H.A. Mechanisms 569 ll.A.i. The Arenium Ion Mechanism 570 ll.A.ii. The SE1 Mechanism 576 11 .B . Orientation and Reactivity 576 11 .Bi. Orientation and Reactivity in Monosubstituted Benzene Rings 576 ll.B.ii. The Ortho/ParaRatio 580 ll.B.ni. Ipso Attack 581 ll.B.iv. Orientation in Benzene Rings with More Than One Substituent 583 11 ,B . v. Orientation in Other Ring Systems 5 84 11 .C. Quantitative Treatments of Reactivity in the Substrate 586 11 .D. A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship 588 11 .E. The Effect of the Leaving Group 591 ILE Reactions 591 11 .F.i. Hydrogen as the Leaving Group in Simple Substitution Reactions 592 11 .F.ii. Hydrogen as the Leaving Group in Rearrangement Reactions 635 ll.F.iii. Other Leaving Groups 641 X CONTENTS 12. Aliphatic, Alkenyl, and Alkynyl Substitution, Electrophilic and Organometallic 649 12. A. Mechanisms 650 12. A.i. Bimolecular Mechanisms: Se2 and SpJL 650 12. А.п. The SE1 Mechanism 654 12. A.ui. Electrophilic Substitution Accompanied by Double-Bond Shifts 657 12.A.1V. Other Mechanisms 658 12.B. Reactivity 658 12. С Reactions 660 12. Ci. Hydrogen as Leaving Group 660 12.C.11. Metals as Leaving Groups 698 12.0.111. Halogen as Leaving Group 713 12.Civ. Carbon Leaving Groups 718 12.C.V. Electrophilic Substitution at Nitrogen 727 13. Aromatic Substitution: Nucleophilic and Organometallic 732 13 .A. Mechanisms 732 13.А.І. The SNAx Mechanism 732 13.A.Ü. The SN1 Mechanism 735 13. A.iii. The Benzynę Mechanism 737 13. A. iv. The SRN1 Mechanism 739 13. A.v. Other Mechanisms 740 13. B. Reactivity 741 ІЗ.В.і. The Effect of Substrate Structure 741 13.B.Ü. The Effect of the Leaving Group 744 13.В.Ш. The Effect of the Attacking Nucleophile 745 13. С Reactions 745 13. Ci. All Leaving Groups Except Hydrogen and N2+ 746 ІЗ.С.іі. Hydrogen as Leaving Group 784 13. Ciii. Nitrogen as Leaving Group 788 13. Civ. Rearrangements 797 14. Substitution Reactions: Radical 803 14. A. Mechanisms 803 H.A.i. Radical Mechanisms in General 803 14.А.ІІ. Free Radical Substitution Mechanisms 807 H.A.iii. Mechanisms at an Aromatic Substrate 809 14. A. iv. Neighboring-Group Assistance in Free Radical Reactions 810 14. B. Reactivity 812 14. B.i. Reactivity for Aliphatic Substrates 812 14.B.Ü. Reactivity at a Bridgehead 817 14.В.ІІІ. Reactivity in Aromatic Substrates 818 14.B.ÌV. Reactivity in the Attacking Radical 819 14.B.V. The Effect of Solvent on Reactivity 820 CONTENTS Xl 14.C. Reactions 821 14. Ci. Hydrogen as a Leaving Group 821 M.C.ii. N2 as Leaving Group 846 14. C. iii. Metals as Leaving Groups 849 14. С. iv. Halogen as Leaving Group 851 14.Cv. Sulfur as Leaving Group 851 14.Cvi. Carbon as Leaving Group 853 15. Addition to Carbon-Carbon Multiple Bonds 859 1 5.A. Mechanisms 859 15. A.i. Electrophilic Addition 859 lS.A.ii. Nucleophilic Addition 865 15. A.iii. Free Radical Addition 867 15. A. iv. Cyclic Mechanisms 869 15.A.V. Addition to Conjugated Systems 869 15. B. Orientation and Reactivity 871 15.В.І. Reactivity 871 15.B.Ü. Orientation 874 15.В.ІІІ. Stereochemical Orientation 877 15.B.ÍV. Addition to Cyclopropane Rings 879 15.C. Reactions 881 15.С.І. Isomerization of Double and Triple Bonds 881 15.С.ІІ. Reactions in which Hydrogen Adds to One Side 883 15. Ciii. Reactions in which Hydrogen Adds to Neither Side 981 15.Civ. Cycloaddition Reactions 1014 16. Addition to Carbon-Hetero Multiple Bonds 1067 16. A. Mechanism and Reactivity 1067 16.А.І. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 1069 I6.B. Reactions 1075 16.В.І. Reactions in which Hydrogen or a Metallic Ion Adds to the Heteroatom 1075 16.B.Ü. Acyl Substitution Reactions 1189 16.В.ІІІ. Reactions in which Carbon Adds to the Heteroatom 1239 16.B.ÍV. Addition to Isocyanides 1246 16.B.V. Nucleophilic Substitution at a Sulfonyl Sulfur Atom 1248 17. Eliminations 1253 17.A. Mechanisms and Orientation 1253 17. Ai. The E2 Mechanism 1254 17.A.Ü. The El Mechanism 1261 П.А.ііі. The ElcB Mechanism 1262 17.A.ÍV. The E 1-E2-EI cB Spectrum 1267 17.A.V. The E2C Mechanism 1268 1 7.B. Regiochemistry of the Double Bond 1269 XII CONTENTS 17. С. Stereochemistry of the Double Bond 1273 17.D. Reactivity 1274 17.D.Í. Effect of Substrate Structure 1274 17.0.11. Effect of the Attacking Base 1276 17.D.ÜÍ. Effect of the Leaving Group 1276 17.D.1V. Effect of the Medium 1277 17. E. Mechanisms and Orientation in Pyrolytic Eliminations 1278 17.Е.І. Mechanisms 1278 17.E.11. Orientation in Pyrolytic Eliminations 1281 17.Е.ІІІ. M-Conjugate Eliminations 1282 17.F. Reactions 1282 17.Fi. Reactions in which C=C and C=C Bonds are Formed 1282 17.F.Ü. Fragmentations 1307 17. Fiii. Reactions in which C^N or C=N Bonds are Formed 1310 17.F.ÍV. Reactions in which С—О Bonds are Formed 1314 17.F.V. Reactions in which N=N Bonds are Formed 1315 17.F.V1. Extrusion Reactions 1316 18. Rearrangements 1321 18.A. Mechanisms 1322 18. A.i. Nucleophilic Rearrangements 1322 18. A.n. The Actual Nature of the Migration 1324 18.А.ІІІ. Migratory Aptitudes 1328 18.A.1V. Memory Effects 1330 18. B. Longer Nucleophilic Rearrangements 1331 18. С Free Radical Rearrangements 1333 18. D. Carbene Rearrangements 1337 18. E. Electrophilic Rearrangements 1337 18.F. Reactions 1337 18.Fi. 1 ,2-Rearrangements 1338 18.F.Ü. Non- 1,2 Rearrangements 1380 19. Oxidations and Reductions 1433 19. A. Mechanisms 1434 19. B. Reactions 1436 19.В.І. Oxidations 1437 19.BÜ. Reductions 1497 APPENDIX A: THE LITERATURE OF ORGANIC CHEMISTRY 1569 APPENDIX B: CLASSIFICATION OF REACTIONS BY TYPE OF COMPOUNDS SYNTHESIZED 1605 INDEXES AUTHOR INDEX 1631 SUBJECT INDEX 1835
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author	Smith, Michael B. 1946-
author_GND	(DE-588)136061559 (DE-588)131388568
author_facet	Smith, Michael B. 1946-
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dewey-hundreds	500 - Natural sciences and mathematics
dewey-ones	547 - Organic chemistry
dewey-raw	547
dewey-search	547
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dewey-tens	540 - Chemistry and allied sciences
discipline	Chemie / Pharmazie Chemie
edition	7th ed.
format	Book
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genre	1\p (DE-588)4123623-3 Lehrbuch gnd-content
genre_facet	Lehrbuch
id	DE-604.BV040283427
illustrated	Illustrated
indexdate	2024-07-10T00:20:44Z
institution	BVB
isbn	9780470462591
language	English
oai_aleph_id	oai:aleph.bib-bvb.de:BVB01-025138746
oclc_num	802515522
open_access_boolean
owner	DE-91G DE-BY-TUM DE-20 DE-11 DE-355 DE-BY-UBR DE-29T DE-188 DE-1102 DE-703 DE-19 DE-BY-UBM DE-83
owner_facet	DE-91G DE-BY-TUM DE-20 DE-11 DE-355 DE-BY-UBR DE-29T DE-188 DE-1102 DE-703 DE-19 DE-BY-UBM DE-83
physical	XXV, 2047 S. Ill., graph. Darst.
publishDate	2013
publishDateSearch	2013
publishDateSort	2013
publisher	Wiley
record_format	marc
spelling	Smith, Michael B. 1946- Verfasser (DE-588)136061559 aut March's advanced organic chemistry reactions, mechanisms, and structure Michael B. Smith Advanced organic chemistry 7th ed. Hoboken, NJ Wiley 2013 XXV, 2047 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Chemie (DE-588)4043793-0 gnd rswk-swf Reaktionsmechanismus (DE-588)4177123-0 gnd rswk-swf Reaktivität (DE-588)4208182-8 gnd rswk-swf Chemischer Prozess (DE-588)4147636-0 gnd rswk-swf Chemische Struktur (DE-588)4009857-6 gnd rswk-swf Chemische Reaktion (DE-588)4009853-9 gnd rswk-swf Chemische Bindung (DE-588)4009843-6 gnd rswk-swf 1\p (DE-588)4123623-3 Lehrbuch gnd-content Reaktionsmechanismus (DE-588)4177123-0 s Organische Chemie (DE-588)4043793-0 s DE-604 Chemische Reaktion (DE-588)4009853-9 s Chemische Struktur (DE-588)4009857-6 s Chemischer Prozess (DE-588)4147636-0 s 2\p DE-604 Reaktivität (DE-588)4208182-8 s Chemische Bindung (DE-588)4009843-6 s 3\p DE-604 March, Jerry 1929-1997 Sonstige (DE-588)131388568 oth Früher u.d.T. March, Jerry Advanced organic chemistry (DE-604)BV007464030 Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025138746&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 2\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 3\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk
spellingShingle	Smith, Michael B. 1946- March's advanced organic chemistry reactions, mechanisms, and structure Organische Chemie (DE-588)4043793-0 gnd Reaktionsmechanismus (DE-588)4177123-0 gnd Reaktivität (DE-588)4208182-8 gnd Chemischer Prozess (DE-588)4147636-0 gnd Chemische Struktur (DE-588)4009857-6 gnd Chemische Reaktion (DE-588)4009853-9 gnd Chemische Bindung (DE-588)4009843-6 gnd
subject_GND	(DE-588)4043793-0 (DE-588)4177123-0 (DE-588)4208182-8 (DE-588)4147636-0 (DE-588)4009857-6 (DE-588)4009853-9 (DE-588)4009843-6 (DE-588)4123623-3
title	March's advanced organic chemistry reactions, mechanisms, and structure
title_alt	Advanced organic chemistry
title_auth	March's advanced organic chemistry reactions, mechanisms, and structure
title_exact_search	March's advanced organic chemistry reactions, mechanisms, and structure
title_full	March's advanced organic chemistry reactions, mechanisms, and structure Michael B. Smith
title_fullStr	March's advanced organic chemistry reactions, mechanisms, and structure Michael B. Smith
title_full_unstemmed	March's advanced organic chemistry reactions, mechanisms, and structure Michael B. Smith
title_old	March, Jerry Advanced organic chemistry
title_short	March's advanced organic chemistry
title_sort	march s advanced organic chemistry reactions mechanisms and structure
title_sub	reactions, mechanisms, and structure
topic	Organische Chemie (DE-588)4043793-0 gnd Reaktionsmechanismus (DE-588)4177123-0 gnd Reaktivität (DE-588)4208182-8 gnd Chemischer Prozess (DE-588)4147636-0 gnd Chemische Struktur (DE-588)4009857-6 gnd Chemische Reaktion (DE-588)4009853-9 gnd Chemische Bindung (DE-588)4009843-6 gnd
topic_facet	Organische Chemie Reaktionsmechanismus Reaktivität Chemischer Prozess Chemische Struktur Chemische Reaktion Chemische Bindung Lehrbuch
url	http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025138746&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
work_keys_str_mv	AT smithmichaelb marchsadvancedorganicchemistryreactionsmechanismsandstructure AT marchjerry marchsadvancedorganicchemistryreactionsmechanismsandstructure AT smithmichaelb advancedorganicchemistry AT marchjerry advancedorganicchemistry

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