Electron flow in organic chemistry [[electronic resource] ] : a decision-based guide to organic mechanisms / / Paul H. Scudder, New College of Florida |
Autore | Scudder Paul H |
Edizione | [2nd ed.] |
Pubbl/distr/stampa | Hoboken, N.J., : Wiley, 2013 |
Descrizione fisica | xv, 432 p. : ill |
Disciplina | 547/.128 |
Soggetto topico |
Charge exchange
Chemical bonds Chemistry, Organic |
ISBN |
1118355016
9781118355015 |
Classificazione |
437
547/.128 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto | Machine generated contents note: 1 BONDING AND ELECTRON DISTRIBUTION 1 1.1 The Decision-Based Approach To Organic Chemistry 2 1.2 Ionic And Covalent Bonding 6 1.3 Lewis Structures And Resonance Forms 8 1.4 Curved-Arrow Notation 11 1.5 Nomenclature And Abbreviations 16 1.6 An Orbital View Of Bonding (Supplemental) 18 1.7 The Shapes Of Molecules 21 1.8 Molecular Repulsions, Attractions, And Hydrogen Bonding 25 1.9 Conjugation, Vinylogy, Aromaticity 27 1.10 Summary 30 2 THE PROCESS OF BOND FORMATION 34 2.1 Energetics Control Knowledge 35 2.2 Orbital Overlap In Covalent Bond Formation 35 2.3 Orbital Interaction Diagrams 38 2.4 Polarizability And Hard And Soft Acid?Base Theory 41 2.5 Thermodynamics, Position Of Equilibrium 43 2.6 Kinetics, Rate Of Reaction 47 2.7 Solvent Stabilization Of Ions 53 2.8 Enzymatic Catalysis - Lessons From Biochemistry 55 2.9 Summary 57 3 PROTON TRANSFER AND THE PRINCIPLES OF STABILITY 61 3.1 Introduction To Proton Transfer 62 3.2 Ranking Of Acids And Bases, The pKa Chart 63 3.3 Structural Factors That Influence Acid Strength 66 3.4 Structural Factors That Influence Base Strength 70 3.5 Carbon Acids & Ranking Of Electron-Withdrawing Groups 71 3.6 Calculation Of Keq For Proton Transfer 76 3.7 Proton Transfer Mechanisms 77 3.8 Common Errors 81 3.9 Proton Transfer Product Predictions 82 3.10 Summary 83 4 IMPORTANT REACTION ARCHETYPES 88 4.1 Introduction To Reaction Archetypes 89 4.2 Nucleophilic Substitution At A Tetrahedral Center 89 4.3 Elimination Reactions Create Pi Bonds 110 4.4 Addition Reactions To Polarized Multiple Bonds 124 4.5 Nucleophilic Substitution At A Trigonal Planar Center 133 4.6 Electrophilic Substitution At A Trigonal Planar Center 140 4.7 Rearrangements To An Electrophilic Carbon 144 4.8 Reaction Archetype Summary 146 5 CLASSIFICATION OF ELECTRON SOURCES 151 5.1 Generalized Ranking Of Electron Sources 151 5.2 Nonbonding Electrons 152 5.3 Electron-Rich Sigma Bonds 154 5.4 Electron-Rich Pi Bonds 155 5.5 Simple Pi Bonds 156 5.6 Aromatic Rings 159 5.7 Summary Of Generic Electron Sources 160 6 CLASSIFICATION OF ELECTRON SINKS 166 6.1 Generalized Ranking Of Electron Sinks 166 6.2 Electron-Deficient Species 167 6.3 Weak Single Bonds 168 6.4 Polarized Multiple Bonds Without Leaving Groups 170 6.5 Polarized Multiple Bonds With Leaving Groups 172 6.6 Summary Of Generic Electron Sinks 173 7 THE ELECTRON FLOW PATHWAYS 179 7.1 The Dozen Most Common Pathways 180 7.2 Six Minor Pathways 191 7.3 Common Path Combinations 197 7.4 Variations On A Theme 201 7.5 Twelve Major Paths Summary And Crosschecks 208 8 INTERACTION OF ELECTRON SOURCES AND SINKS 213 8.1 Source And Sink Correlation Matrix 214 8.2 H-A Sinks Reacting With Common Sources 214 8.3 Y?L Sinks Reacting With Common Sources 218 8.4 sp3 C?L Sinks Reacting With Common Sources 222 8.5 C=Y Sinks Reacting With Common Sources 227 8.6 R?C?Y Sinks Reacting With Common Sources 233 8.7 C=C?Ewg Sinks Reacting With Common Sources 235 8.8 L?C=Y Sinks Reacting With Common Sources 237 8.9 Miscellaneous Reactions 240 8.10 Metal Ions As Electron Sinks 242 8.11 Rearrangements To An Electrophilic Center 243 8.12 Nu-L Reactions 244 8.13 Product Matrix Summary 248 9 DECISIONS, DECISIONS 251 9.1 Decision Point Recognition 252 9.2 Multiple Additions 252 9.3 Regiochemistry & Stereochemistry Of Enolate Formation 254 9.4 Ambident Nucleophiles 255 9.5 Substitution Vs. Elimination 258 9.6 Ambident Electrophiles 262 9.7 Intermolecular Vs. Intramolecular 263 9.8 To Migrate Or Not To An Electrophilic Center 264 9.8 Summary 266 10 CHOOSING THE MOST PROBABLE PATH 269 10.1 Problem-Solving In General 270 10.2 General Mechanistic Cross-Checks 274 10.3 The Path-Selection Process 276 10.4 Reaction Mechanism Strategies 278 10.5 Worked Mechanism Examples 279 10.6 Product Prediction Strategies 297 10.7 Worked Product Prediction Examples 297 10.8 Methods For Testing Mechanisms 313 10.9 Lessons from Biochemical Mechanisms 319 10.10 Summary 321 11 ONE-ELECTRON PROCESSES 326 11.1 Radical Structure And Stability 326 11.2 Radical Path Initiation 329 11.3 Major Paths For Radicals Reacting With Neutrals 330 11.4 Unimolecular Radical Paths 332 11.5 Termination Radical Paths 333 11.6 Radical Path Combinations 333 11.7 Approaches To Radical Mechanisms 336 11.8 Single Electron Transfer, S.E.T., And Charged Radicals 338 11.9 Dissolving Metal Reductions 339 11.10 Electron Transfer Initiated Processes 340 11.11 One-Electron Path Summary 340 12 QUALITATIVE M.O. THEORY & PERICYCLIC REACTIONS 343 12.1 Review Of Orbitals As Standing Waves 344 12.2 Molecular Orbital Theory For Linear Pi Systems 344 12.3 Molecular Orbital Theory For Cyclic Conjugated PI Systems 348 12.4 Perturbation Of The HOMO And LUMO 351 12.5 Delocalization Of Sigma Electrons (Supplemental) 352 12.6 Concerted Pericyclic Cycloaddition Reactions 353 12.7 Concerted Pericyclic Electrocyclic Reactions 357 12.8 Concerted Pericyclic Sigmatropic Rearrangements 359 12.9 Pericyclic Reactions Summary 361 APPENDIX (A COLLECTION OF IMPORTANT TOOLS) 364 General Bibliography 364 Abbreviations Used in This Text 365 Functional Group Glossary 366 Composite pKa Chart 369 Bond Strength Table 372 Generic Classification Guide 373 Flow Charts for the Classification of Electron Sources and Sinks 375 Pathway Summary 375 Trends Guide 380 Major Routes Summary 384 Major Decisions Guide 388 Thermodynamics and Kinetics 390 Generation of Alternate Paths, Reaction Cubes 390 Organic Structure Elucidation Strategies 393 Notes on Nomenclature 399 HINTS TO PROBLEMS FROM CHAPTERS 8, 9, AND 10 404 INDEX 407. |
Record Nr. | UNINA-9910795948903321 |
Scudder Paul H | ||
Hoboken, N.J., : Wiley, 2013 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
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Keynotes in organic chemistry / / Andrew F. Parsons |
Autore | Parsons A. F |
Edizione | [Second edition.] |
Pubbl/distr/stampa | Chichester, West Sussex : , : Wiley, , 2014 |
Descrizione fisica | 1 online resource (302 pages) : illustrations |
Disciplina | 547 |
Soggetto topico | Chemistry, Organic |
ISBN |
1-118-67642-4
1-118-67641-6 |
Classificazione |
437
547 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Record Nr. | UNINA-9910796096603321 |
Parsons A. F | ||
Chichester, West Sussex : , : Wiley, , 2014 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
March's advanced organic chemistry : reactions, mechanisms, and structure / / Michael B. Smith |
Autore | Smith Michael <1946 Oct. 17-> |
Edizione | [7th ed.] |
Pubbl/distr/stampa | Hoboken, N.J., : Wiley, c2013 |
Descrizione fisica | 1 online resource (2075 p.) |
Disciplina | 547 |
Soggetto topico | Chemistry, Organic |
ISBN |
1-5231-0988-2
1-299-63397-8 1-118-47225-X 1-118-47221-7 |
Classificazione | 437 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto | Localized chemical bonding -- Delocalized chemical bonding -- Bonding weaker than covalent -- Stereochemistry and conformation -- Carbocations, carbanions, free radicals, carbenes, and nitrenes -- Mechanisms and methods of determining them -- Irradiation processes in organic chemistry -- Acids and bases -- Effects of structure and medium on reactivity -- Aliphatic substitution, nucleophilic and organometallic -- Aromatic substitution, electrophilic -- Aliphatic, alkenyl, and alkynyl substitution, electrophilic and organometallic -- Aromatic substitution, nucleophilic and organometallic -- Substitution reactions, radical -- Addition to carbon-carbon multiple bonds -- Addition to carbon-hetero multiple bonds -- Eliminations -- Rearrangements -- Oxidations and reductions -- Appendix A. The literature of organic chemistry -- Appendix B. Classification of reactions by type of compounds synthesized. |
Record Nr. | UNINA-9910812258503321 |
Smith Michael <1946 Oct. 17-> | ||
Hoboken, N.J., : Wiley, c2013 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
Organic chemistry : an intermediate text / / Robert V. Hoffman |
Autore | Hoffman Robert V |
Edizione | [2nd ed] |
Pubbl/distr/stampa | Hoboken, N.J., : Wiley-Interscience, c2004 |
Descrizione fisica | 1 online resource (494 p.) |
Disciplina | 547 |
Soggetto topico | Chemistry, Organic |
ISBN |
1-280-26490-X
9786610264902 0-470-24493-3 0-471-64872-8 0-471-64873-6 |
Classificazione |
437
547 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | und |
Nota di contenuto | ORGANIC CHEMISTRY SECOND EDITION; CONTENTS; Preface; Preface to the First Edition; 1 Functional Groups and Chemical Bonding; 2 Oxidation States of Organic Compounds; 3 Acidity and Basicity; 4 Curved-Arrow Notation; 5 Mechanisms of Organic Reactions; 6 Stereochemical and Conformational Isomerism; 7 Functional Group Synthesis; 8 Carbon-Carbon Bond Formation between Carbon Nucleophiles and Carbon Electrophiles; 9 Carbon-Carbon Bond Formation by Free-Radical Reactions; 10 Planning Organic Syntheses; 11 Structure Determination of Organic Compounds; Solutions to Chapter Problems; Index |
Record Nr. | UNINA-9910829880903321 |
Hoffman Robert V | ||
Hoboken, N.J., : Wiley-Interscience, c2004 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
Organic chemistry : an intermediate text / / Robert V. Hoffman |
Edizione | [2nd ed] |
Pubbl/distr/stampa | Hoboken, N.J., : Wiley-Interscience, c2004 |
Descrizione fisica | 1 online resource (494 p.) |
Disciplina | 547 |
Soggetto topico | Chemistry, Organic |
ISBN |
1-280-26490-X
9786610264902 0-470-24493-3 0-471-64872-8 0-471-64873-6 |
Classificazione |
437
547 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto | ORGANIC CHEMISTRY SECOND EDITION; CONTENTS; Preface; Preface to the First Edition; 1 Functional Groups and Chemical Bonding; 2 Oxidation States of Organic Compounds; 3 Acidity and Basicity; 4 Curved-Arrow Notation; 5 Mechanisms of Organic Reactions; 6 Stereochemical and Conformational Isomerism; 7 Functional Group Synthesis; 8 Carbon-Carbon Bond Formation between Carbon Nucleophiles and Carbon Electrophiles; 9 Carbon-Carbon Bond Formation by Free-Radical Reactions; 10 Planning Organic Syntheses; 11 Structure Determination of Organic Compounds; Solutions to Chapter Problems; Index |
Record Nr. | UNINA-9910876995203321 |
Hoboken, N.J., : Wiley-Interscience, c2004 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
Organic synthesis : the disconnection approach / / Stuart Warren and Paul Wyatt |
Autore | Warren Stuart G |
Edizione | [2nd ed.] |
Pubbl/distr/stampa | Chichester, : Wiley, 2008 |
Descrizione fisica | 1 online resource (viii, 329 p.) : ill |
Disciplina | 547.2 |
Altri autori (Persone) | WyattPaul |
Soggetto topico | Organic compounds - Synthesis |
ISBN |
9781119965534 (e-book)
9780470712375 (hbk.) 9780470712368 (pbk.) |
Classificazione |
437
547/.2 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto | 1. The disconnection approach -- 2. Basic principles: synthons and reagents synthesis of aromatic compounds -- 3. Strategy I: the order of events -- 4. One-group C-X disconnections -- 5. Strategy II: chemoselectivity -- 6. Two-group C-X disconnections -- 7. Strategy III: reversal of polarity, cyclisations, summary of strategy -- 8. Amine synthesis -- 9. Strategy IV: protecting groups -- 10. One group C-C disconnections I: alcohols -- 11. General strategy A: choosing a disconnection -- 12. Strategy V: stereoselectivity A -- 13. One group C-C disconnections II: carbonyl compounds -- 14. Strategy VI: regioselectivity -- 15. Alkene synthesis -- 16. Strategy VII: use of acetylenes (alkynes) -- 17. Two-group C-C disconnections I: Diels-Alder reactions -- 18. Strategy VIII: introduction to carbonyl condensations -- 19. Two-group C-C disconnections II: 1,3-difunctionalised compounds -- 20. Strategy IX: control in carbonyl condensations -- 21. Two-group C-C disconnections: 1,5-difunctionalised compounds conjugate (Michael) addition and Robinson annelation -- 22. Strategy X: aliphatic nitro compounds in synthesis -- 23. Two-group disconnections IV: 1,2-difunctionalised compounds -- 24. Strategy XI: radical reactions in synthesis -- 25. Two-group disconnections V: 1,4-difunctionalised compounds -- 26. Strategy XII: reconnection -- 27. Two-group C-C disconnections VI: 1,6-diCarbonyl compounds -- 28. General strategy B: strategy of carbonyl disconnections -- 29. Strategy XIII: introduction to ring synthesis: saturated heterocycles -- 30. Three-membered rings -- 31. Strategy XIV: rearrangements in synthesis -- 32. Four-membered rings: photochemistry in synthesis -- 33. Strategy XV: the use of ketenes in synthesis -- 34. Five-membered rings -- 35. Strategy XVI: pericyclic reactions in synthesis: special methods for five-membered rings -- 36. Six-membered rings -- 37. General strategy C: strategy of ring synthesis -- 38. Strategy XVII: stereoselectivity B -- 39. Aromatic heterocycles -- 40. General strategy D : advanced strategy -- Index. |
Record Nr. | UNINA-9910790031403321 |
Warren Stuart G | ||
Chichester, : Wiley, 2008 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|
Organic synthesis : the disconnection approach / / Stuart Warren and Paul Wyatt |
Autore | Warren Stuart G |
Edizione | [2nd ed.] |
Pubbl/distr/stampa | Chichester, : Wiley, 2008 |
Descrizione fisica | 1 online resource (viii, 329 p.) : ill |
Disciplina | 547.2 |
Altri autori (Persone) | WyattPaul |
Soggetto topico | Organic compounds - Synthesis |
ISBN |
9781119965534 (e-book)
9780470712375 (hbk.) 9780470712368 (pbk.) |
Classificazione |
437
547/.2 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Nota di contenuto | 1. The disconnection approach -- 2. Basic principles: synthons and reagents synthesis of aromatic compounds -- 3. Strategy I: the order of events -- 4. One-group C-X disconnections -- 5. Strategy II: chemoselectivity -- 6. Two-group C-X disconnections -- 7. Strategy III: reversal of polarity, cyclisations, summary of strategy -- 8. Amine synthesis -- 9. Strategy IV: protecting groups -- 10. One group C-C disconnections I: alcohols -- 11. General strategy A: choosing a disconnection -- 12. Strategy V: stereoselectivity A -- 13. One group C-C disconnections II: carbonyl compounds -- 14. Strategy VI: regioselectivity -- 15. Alkene synthesis -- 16. Strategy VII: use of acetylenes (alkynes) -- 17. Two-group C-C disconnections I: Diels-Alder reactions -- 18. Strategy VIII: introduction to carbonyl condensations -- 19. Two-group C-C disconnections II: 1,3-difunctionalised compounds -- 20. Strategy IX: control in carbonyl condensations -- 21. Two-group C-C disconnections: 1,5-difunctionalised compounds conjugate (Michael) addition and Robinson annelation -- 22. Strategy X: aliphatic nitro compounds in synthesis -- 23. Two-group disconnections IV: 1,2-difunctionalised compounds -- 24. Strategy XI: radical reactions in synthesis -- 25. Two-group disconnections V: 1,4-difunctionalised compounds -- 26. Strategy XII: reconnection -- 27. Two-group C-C disconnections VI: 1,6-diCarbonyl compounds -- 28. General strategy B: strategy of carbonyl disconnections -- 29. Strategy XIII: introduction to ring synthesis: saturated heterocycles -- 30. Three-membered rings -- 31. Strategy XIV: rearrangements in synthesis -- 32. Four-membered rings: photochemistry in synthesis -- 33. Strategy XV: the use of ketenes in synthesis -- 34. Five-membered rings -- 35. Strategy XVI: pericyclic reactions in synthesis: special methods for five-membered rings -- 36. Six-membered rings -- 37. General strategy C: strategy of ring synthesis -- 38. Strategy XVII: stereoselectivity B -- 39. Aromatic heterocycles -- 40. General strategy D : advanced strategy -- Index. |
Record Nr. | UNINA-9910816493803321 |
Warren Stuart G | ||
Chichester, : Wiley, 2008 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
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Perspectives on structure and mechanism in organic chemistry / / Felix A. Carroll |
Autore | Carroll Felix A. |
Edizione | [Second edition.] |
Pubbl/distr/stampa | Hoboken, New Jersey : , : John Wiley, , [2010] |
Descrizione fisica | 1 online resource (966 pages) : illustrations |
Disciplina | 547/.13 |
Soggetto topico | Physical organic chemistry |
ISBN |
1118018176
9781118018170 |
Classificazione |
437
547.1 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Record Nr. | UNINA-9910795801503321 |
Carroll Felix A. | ||
Hoboken, New Jersey : , : John Wiley, , [2010] | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
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Perspectives on structure and mechanism in organic chemistry / / Felix A. Carroll |
Autore | Carroll Felix A. |
Edizione | [Second edition.] |
Pubbl/distr/stampa | Hoboken, New Jersey : , : John Wiley, , [2010] |
Descrizione fisica | 1 online resource (966 pages) : illustrations |
Disciplina | 547/.13 |
Soggetto topico | Physical organic chemistry |
ISBN |
1118018176
9781118018170 |
Classificazione |
437
547.1 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | eng |
Record Nr. | UNINA-9910822319403321 |
Carroll Felix A. | ||
Hoboken, New Jersey : , : John Wiley, , [2010] | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
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マンガでわかる有機化学 [[マンガデワカルユウキカガク]] |
Pubbl/distr/stampa | 東京, : オーム社, 2014.3 |
Descrizione fisica | オンライン資料1件 |
Soggetto topico | 有機化学 |
ISBN | 4-274-80219-1 |
Classificazione | 437 |
Formato | Materiale a stampa |
Livello bibliografico | Monografia |
Lingua di pubblicazione | jpn |
Nota di contenuto | 表紙 -- クレジット -- まえがき -- 目次 -- プロローグ 異星からの伝道師 -- 第1章 化学の基礎 -- 1.1 化学って何? -- 1.2 有機化合物の分子の骨格は炭素原子である -- 1.3 原子の構造と化学結合(原子の構造) -- フォローアップ -- 原子の構造 -- 軌道と電子配置 -- sp3混成軌道と単結合 -- コラム 料理は有機化学の実験 -- 第2章 有機化学の基礎 -- 2.1 有機化合物の性質の源(官能基) -- 2.2 有機化合物の名前のつけ方 -- フォローアップ -- 二重結合と三重結合 -- 共役と共鳴 -- コラム 目に見える巨大分子 -- 第3章 有機化合物の構造 -- 3.1 異性体って何? -- 3.2 分子の二次元構造と性質(立体配置) -- 3.3 分子の三次元構造、分子の鏡の世界(鏡像異性体) -- フォローアップ -- 分子式、構造式の見方と書き方 -- E,Z命名法 -- 立体異性体のさまざまな表示の仕方 -- R,S命名法 -- 立体配座 -- コラム 物質の匂いが立体構造で変わる -- 第4章 有機化合物の性質 -- 4.1 水に溶けるものと油に溶けるもの(親水性・親油性) -- 4.2 沸点の違いを生む原因(分子間相互作用・分極した結合) -- 4.3 酸と塩基 -- 4.4 正六角形の構造を持つベンゼンという芳香族化合物 -- フォローアップ -- 酸と塩基 -- ベンゼンの構造 -- ケト-エノール互変異性って何 -- コラム 香りの物質は脂溶性 -- 第5章 有機化合物の反応 -- 5.1 有機化合物はさまざまな反応で別の分子に変わる -- 5.2 炭化水素の反応 -- 5.3 アルコールの反応 -- フォローアップ -- エステル化反応 -- 二重結合への付加反応 -- ハロゲン化炭化水素の求核置換反応 -- ハロゲン化炭化水素の脱離反応 -- ベンゼンの反応(芳香族求電子置換反応) -- コラム 物質の性質を操る力 -- 有機化学反応 -- エピローグ -- 付録 生体を作っている有機化合物 -- 生体を構成する主な有機化合物の概観 -- タンパク質 -- 脂質 -- 糖質 -- 合成高分子化合物 -- 参考文献 -- 索引 -- 著者紹介 -- 奥付. |
Record Nr. | UNINA-9910149149403321 |
東京, : オーム社, 2014.3 | ||
Materiale a stampa | ||
Lo trovi qui: Univ. Federico II | ||
|