100 Q & A About Liver Cancer Second Edition 100 Questions & Answers About by Ghassan Abou-Alfa, JONES & BARTLETT

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JONES & BARTLETT 100 Q & A About Liver Cancer Second Edition 100 Questions & Answers About by Ghassan Abou-Alfa

EMPOWER YOURSELF! Whether you're a newly diagnosed liver cancer patient, a survivor, or a friend or relative of either, this book offers help. The only text to provide the doctor's and patient's views, 100 Questions & Answers About Liver Cancer, Second Edition gives you authoritative, practical answers to your questions about treatment options, post-treatment quality of life, sources of support, and much more. Written by a medical oncologist and a gastrointestinal surgeon, with actual patient commentary, this book is an invaluable resource for anyone coping with the physical and emotional turmoil of this frightening disease._x000D_ _x000D_ New Reaction Sections Correlation: 7th Edition 8th Edition xv_x000D_ _x000D_ _x000D_ Preface xxi_x000D_ _x000D_ _x000D_ Common Abbreviations xxv_x000D_ _x000D_ _x000D_ Biographical Statement xxxi_x000D_ _x000D_ _x000D_ New Features of the 8th Edition xxxiii_x000D_ _x000D_ _x000D_ Part I Introduction 1_x000D_ _x000D_ _x000D_ 1. Localized Chemical Bonding 3_x000D_ _x000D_ _x000D_ 1.A. Covalent Bonding 3_x000D_ _x000D_ _x000D_ 1.B. Multiple Valence 7_x000D_ _x000D_ _x000D_ 1.C. Hybridization 7_x000D_ _x000D_ _x000D_ 1.D. Multiple Bonds 9_x000D_ _x000D_ _x000D_ 1.E. Photoelectron Spectroscopy 12_x000D_ _x000D_ _x000D_ 1.F. Electronic Structures of Molecules 15_x000D_ _x000D_ _x000D_ 1.G. Electronegativity 17_x000D_ _x000D_ _x000D_ 1.H. Dipole Moment 19_x000D_ _x000D_ _x000D_ 1.I. Inductive and Field Effects 20_x000D_ _x000D_ _x000D_ 1.J. Bond Distances 23_x000D_ _x000D_ _x000D_ 1.K. Bond Angles 27_x000D_ _x000D_ _x000D_ 1.L. Bond Energies 29_x000D_ _x000D_ _x000D_ 2. Delocalized Chemical Bonding 33_x000D_ _x000D_ _x000D_ 2.A. Molecular Orbitals 34_x000D_ _x000D_ _x000D_ 2.B. Bond Energies and Distances in Compounds Containing Delocalized Bonds 37_x000D_ _x000D_ _x000D_ 2.C. Molecules that have Delocalized Bonds 39_x000D_ _x000D_ _x000D_ 2.D. Cross Conjugation 44_x000D_ _x000D_ _x000D_ 2.E. The Rules of Resonance 46_x000D_ _x000D_ _x000D_ 2.F. The Resonance Effect 48_x000D_ _x000D_ _x000D_ 2.G. Steric Inhibition of Resonance and the Influences of Strain 48_x000D_ _x000D_ _x000D_ 2.H. p -d Bonding: Ylids 52_x000D_ _x000D_ _x000D_ 2.I. Aromaticity 54_x000D_ _x000D_ _x000D_ 2.I.i. Six-Membered Rings 58_x000D_ _x000D_ _x000D_ 2.I.ii. Five-, Seven-, and Eight-Membered Rings 62_x000D_ _x000D_ _x000D_ 2.I.iii. Other Systems Containing Aromatic Sextets 67_x000D_ _x000D_ _x000D_ 2.J. Alternant and Nonalternant Hydrocarbons 68_x000D_ _x000D_ _x000D_ 2.K. Aromatic Systems with Electron Numbers Other Than Six 70_x000D_ _x000D_ _x000D_ 2.K.i. Systems of Two Electrons 72_x000D_ _x000D_ _x000D_ 2.K.ii. Systems of Four Electrons: Antiaromaticity 73_x000D_ _x000D_ _x000D_ 2.K.iii. Systems of Eight Electrons 76_x000D_ _x000D_ _x000D_ 2.K.iv. Systems of Ten Electrons 77_x000D_ _x000D_ _x000D_ 2.K.v. Systems of More than Ten Electrons: 4n + 2 Electrons 80_x000D_ _x000D_ _x000D_ 2.K.vi. Systems of More Than Ten Electrons: 4n Electrons 85_x000D_ _x000D_ _x000D_ 2.L. Other Aromatic Compounds 89_x000D_ _x000D_ _x000D_ 2.M. Hyperconjugation 92_x000D_ _x000D_ _x000D_ 2.N. Tautomerism 96_x000D_ _x000D_ _x000D_ 2.N.i. Keto-Enol Tautomerism 97_x000D_ _x000D_ _x000D_ 2.N.ii. Other Proton-Shift Tautomerism 100_x000D_ _x000D_ _x000D_ 3. Bonding Weaker Than Covalent 105_x000D_ _x000D_ _x000D_ 3.A. Hydrogen Bonding 105_x000D_ _x000D_ _x000D_ 3.B. - Interactions 113_x000D_ _x000D_ _x000D_ 3.C. Addition Compounds 114_x000D_ _x000D_ _x000D_ 3.C.i. Electron Donor-Acceptor (EDA) Complexes 114_x000D_ _x000D_ _x000D_ 3.C.ii. Crown Ether Complexes and Cryptates 117_x000D_ _x000D_ _x000D_ 3.C.iii. Inclusion Compounds 122_x000D_ _x000D_ _x000D_ 3.C.iv. Cyclodextrins 125_x000D_ _x000D_ _x000D_ 3.D. Catenanes and Rotaxanes 127_x000D_ _x000D_ _x000D_ 3.E. Cucurbit[n]Uril-Based Gyroscane 131_x000D_ _x000D_ _x000D_ 4. Stereochemistry and Conformation 133_x000D_ _x000D_ _x000D_ 4.A. Optical Activity and Chirality 133_x000D_ _x000D_ _x000D_ 4.B. Dependence of Rotation on Conditions of Measurement 135_x000D_ _x000D_ _x000D_ 4.C. What Kinds of Molecules Display Optical Activity? 136_x000D_ _x000D_ _x000D_ 4.D. The Fischer Projection 147_x000D_ _x000D_ _x000D_ 4.E. Absolute Configuration 148_x000D_ _x000D_ _x000D_ 4.E.i. The Cahn-Ingold-Prelog System 150_x000D_ _x000D_ _x000D_ 4.E.ii. Methods of Determining Configuration 152_x000D_ _x000D_ _x000D_ 4.F. The Cause of Optical Activity 156_x000D_ _x000D_ _x000D_ 4.G. Molecules with More Than One Stereogenic Center 157_x000D_ _x000D_ _x000D_ 4.H. Asymmetric Synthesis 161_x000D_ _x000D_ _x000D_ 4.I. Methods of Resolution 166_x000D_ _x000D_ _x000D_ 4.J. Optical Purity 173_x000D_ _x000D_ _x000D_ 4.K. Cis-Trans Isomerism 175_x000D_ _x000D_ _x000D_ 4.K.i. Cis-Trans Isomerism Resulting from Double Bonds 175_x000D_ _x000D_ _x000D_ 4.K.ii. Cis-Trans Isomerism of Monocyclic Compounds 179_x000D_ _x000D_ _x000D_ 4.K.iii. Cis-Trans Isomerism of Fused and Bridged Ring Systems 180_x000D_ _x000D_ _x000D_ 4.L. Out-In Isomerism 181_x000D_ _x000D_ _x000D_ 4.M. Enantiotopic and Diastereotopic Atoms, Groups, and Faces 183_x000D_ _x000D_ _x000D_ 4.N. Stereospecific and Stereoselective Syntheses 186_x000D_ _x000D_ _x000D_ 4.O. Conformational Analysis 187_x000D_ _x000D_ _x000D_ 4.O.i. Conformation in Open-Chain Systems 188_x000D_ _x000D_ _x000D_ 4.O.ii. Conformation in Six-Membered Rings 194_x000D_ _x000D_ _x000D_ 4.O.iii. Conformation in Six-Membered Rings Containing Heteroatoms 199_x000D_ _x000D_ _x000D_ 4.O.iv. Conformation in Other Rings 202_x000D_ _x000D_ _x000D_ 4.P. Molecular Mechanics 204_x000D_ _x000D_ _x000D_ 4.Q. Strain 206_x000D_ _x000D_ _x000D_ 4.Q.i. Strain in Small Rings 207_x000D_ _x000D_ _x000D_ 4.Q.ii. Strain in Other Rings 213_x000D_ _x000D_ _x000D_ 4.Q.iii. Unsaturated Rings 215_x000D_ _x000D_ _x000D_ 4.Q.iv. Strain Due to Unavoidable Crowding 218_x000D_ _x000D_ _x000D_ 5. Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes 223_x000D_ _x000D_ _x000D_ 5.A. Carbocations 224_x000D_ _x000D_ _x000D_ 5.A.i. Nomenclature 224_x000D_ _x000D_ _x000D_ 5.A.ii. Stability and Structure of Carbocations 224_x000D_ _x000D_ _x000D_ 5.A.iii. The Generation and Fate of Carbocations 234_x000D_ _x000D_ _x000D_ 5.B. Carbanions 237_x000D_ _x000D_ _x000D_ 5.B.i. Stability and Structure 237_x000D_ _x000D_ _x000D_ 5.B.ii. The Structure of Organometallic Compounds 244_x000D_ _x000D_ _x000D_ 5.B.iii. The Generation and Fate of Carbanions 249_x000D_ _x000D_ _x000D_ 5.C. Free Radicals 250_x000D_ _x000D_ _x000D_ 5.C.i. Stability and Structure 250_x000D_ _x000D_ _x000D_ 5.C.ii. The Generation and Fate of Free Radicals 261_x000D_ _x000D_ _x000D_ 5.C.iii. Radical Ions 265_x000D_ _x000D_ _x000D_ 5.D. Carbenes 266_x000D_ _x000D_ _x000D_ 5.D.i. Stability and Structure 266_x000D_ _x000D_ _x000D_ 5.D.ii. The Generation and Fate of Carbenes 269_x000D_ _x000D_ _x000D_ 5.D.iii. N-Heterocyclic Carbenes (NHCs) 274_x000D_ _x000D_ _x000D_ 5.E. Nitrenes 276_x000D_ _x000D_ _x000D_ 6. Mechanisms and Methods of Determining Them 279_x000D_ _x000D_ _x000D_ 6.A. Types of Mechanism 279_x000D_ _x000D_ _x000D_ 6.B. Types of Reaction 280_x000D_ _x000D_ _x000D_ 6.C. Thermodynamic Requirements for Reaction 283_x000D_ _x000D_ _x000D_ 6.D. Kinetic Requirements for Reaction 284_x000D_ _x000D_ _x000D_ 6.E. The Baldwin Rules for Ring Closure 288_x000D_ _x000D_ _x000D_ 6.F. Kinetic and Thermodynamic Control 290_x000D_ _x000D_ _x000D_ 6.G. The Hammond Postulate 291_x000D_ _x000D_ _x000D_ 6.H. Microscopic Reversibility 291_x000D_ _x000D_ _x000D_ 6.I. Marcus Theory 292_x000D_ _x000D_ _x000D_ 6.J. Methods of Determining Mechanisms 293_x000D_ _x000D_ _x000D_ 6.J.i. Identification of Products 293_x000D_ _x000D_ _x000D_ 6.J.ii. Determination of the Presence of an Intermediate 294_x000D_ _x000D_ _x000D_ 6.J.iii. The Study of Catalysis 295_x000D_ _x000D_ _x000D_ 6.J.iv. Isotopic Labeling 296_x000D_ _x000D_ _x000D_ 6.J.v. Stereochemical Evidence 296_x000D_ _x000D_ _x000D_ 6.J.vi. Kinetic Evidence 297_x000D_ _x000D_ _x000D_ 6.J.vii. Isotope Effects 304_x000D_ _x000D_ _x000D_ 6.K. Catalyst Development 308_x000D_ _x000D_ _x000D_ 7. Irradiation Processes and Techniques that Influence Reactions in Organic Chemistry 313_x000D_ _x000D_ _x000D_ 7.A. Photochemistry 314_x000D_ _x000D_ _x000D_ 7.A.i. Excited States and the Ground State 314_x000D_ _x000D_ _x000D_ 7.A.ii. Singlet and Triplet States: "Forbidden" Transitions 316_x000D_ _x000D_ _x000D_ 7.A.iii. Types of Excitation 317_x000D_ _x000D_ _x000D_ 7.A.iv. Nomenclature and Properties of Excited States 318_x000D_ _x000D_ _x000D_ 7.A.v. Photolytic Cleavage 319_x000D_ _x000D_ _x000D_ 7.A.vi. The Fate of the Excited Molecule: Physical Processes 320_x000D_ _x000D_ _x000D_ 7.A.vii. The Fate of the Excited Molecule: Chemical Processes 325_x000D_ _x000D_ _x000D_ 7.A.viii. The Determination of Photochemical Mechanisms 330_x000D_ _x000D_ _x000D_ 7.B. Sonochemistry 331_x000D_ _x000D_ _x000D_ 7.C. Microwave Chemistry 334_x000D_ _x000D_ _x000D_ 7.D. Flow Chemistry 336_x000D_ _x000D_ _x000D_ 7.E. Mechanochemistry 338_x000D_ _x000D_ _x000D_ 8. Acids and Bases 339_x000D_ _x000D_ _x000D_ 8.A. Bronsted Theory 339_x000D_ _x000D_ _x000D_ 8.A.i. Bronsted Acids 340_x000D_ _x000D_ _x000D_ 8.A.ii. Bronsted Bases 347_x000D_ _x000D_ _x000D_ 8.B. The Mechanism of Proton Transfer Reactions 350_x000D_ _x000D_ _x000D_ 8.C. Measurements of Solvent Acidity 352_x000D_ _x000D_ _x000D_ 8.D. Acid and Base Catalysis 355_x000D_ _x000D_ _x000D_ 8.E. Lewis Acids and Bases 357_x000D_ _x000D_ _x000D_ 8.E.i. Hard-Soft Acids-Bases 359_x000D_ _x000D_ _x000D_ 8.F. The Effects of Structure on the Strengths of Acids and Bases 361_x000D_ _x000D_ _x000D_ 8.G. The Effects of the Medium on Acid and Base Strength 370_x000D_ _x000D_ _x000D_ 9. Effects of Structure and Medium on Reactivity 375_x000D_ _x000D_ _x000D_ 9.A. Resonance and Field Effects 375_x000D_ _x000D_ _x000D_ 9.B. Steric Effects 377_x000D_ _x000D_ _x000D_ 9.C. Quantitative Treatments of the Effect of Structure on Reactivity 380_x000D_ _x000D_ _x000D_ 9.D. Effect of Medium on Reactivity and Rate 390_x000D_ _x000D_ _x000D_ 9.E. High Pressure 390_x000D_ _x000D_ _x000D_ 9.F. Water and Other Nonorganic Solvents 391_x000D_ _x000D_ _x000D_ 9.G. Ionic Liquid Solvents 393_x000D_ _x000D_ _x000D_ 9.H. Solventless Reactions 395_x000D_ _x000D_ _x000D_ Part II Introduction 397_x000D_ _x000D_ _x000D_ 10. Aliphatic Substitution, Nucleophilic and Organometallic 403_x000D_ _x000D_ _x000D_ 10.A. Mechanisms 404_x000D_ _x000D_ _x000D_ 10.A.i. The SN2 Mechanism 404_x000D_ _x000D_ _x000D_ 10.A.ii. The SN1 Mechanism 410_x000D_ _x000D_ _x000D_ 10.A.iii. Ion Pairs in the SN1 Mechanism 414_x000D_ _x000D_ _x000D_ 10.A.iv. Mixed SN1 and SN2 Mechanisms 418_x000D_ _x000D_ _x000D_ 10.B. SET Mechanisms 420_x000D_ _x000D_ _x000D_ 10.C. The Neighboring-Group Mechanism 422_x000D_ _x000D_ _x000D_ 10.C.i. Neighboring-Group Participation by and Bonds: Nonclassical Carbocations 425_x000D_ _x000D_ _x000D_ 10.D. The SNi Mechanism 440_x000D_ _x000D_ _x000D_ 10.E. Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements 441_x000D_ _x000D_ _x000D_ 10.F. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 445_x000D_ _x000D_ _x000D_ 10.G. Reactivity 449_x000D_ _x000D_ _x000D_ 10.G.i. The Effect of Substrate Structure 449_x000D_ _x000D_ _x000D_ 10.G.ii. The Effect of the Attacking Nucleophile 457_x000D_ _x000D_ _x000D_ 10.G.iii. The Effect of the Leaving Group 464_x000D_ _x000D_ _x000D_ 10.G.iv. The Effect of the Reaction Medium 469_x000D_ _x000D_ _x000D_ 10.G.v. Phase-Transfer Catalysis 474_x000D_ _x000D_ _x000D_ 10.G.vi. Influencing Reactivity by External Means 477_x000D_ _x000D_ _x000D_ 10.G.vii. Ambident (Bidentant) Nucleophiles: Regioselectivity 478_x000D_ _x000D_ _x000D_ 10.G.viii. Ambident Substrates 481_x000D_ _x000D_ _x000D_ 10.H. Reactions 483_x000D_ _x000D_ _x000D_ 10.H.i. Oxygen Nucleophiles 483_x000D_ _x000D_ _x000D_ 10.H.ii. Sulfur Nucleophiles 506_x000D_ _x000D_ _x000D_ 10.H.iii. Nitrogen Nucleophiles 512_x000D_ _x000D_ _x000D_ 10.H.iv. Halogen Nucleophiles 534_x000D_ _x000D_ _x000D_ 10.H.v. Carbon Nucleophiles 545_x000D_ _x000D_ _x000D_ 11. Aromatic Substitution, Electrophilic 607_x000D_ _x000D_ _x000D_ 11.A. Mechanisms 607_x000D_ _x000D_ _x000D_ 11.A.i. The Arenium Ion Mechanism 608_x000D_ _x000D_ _x000D_ 11.A.ii. The SE1 Mechanism 613_x000D_ _x000D_ _x000D_ 11.B. Orientation and Reactivity 614_x000D_ _x000D_ _x000D_ 11.B.i. Orientation and Reactivity in Monosubstituted Benzene Rings 614_x000D_ _x000D_ _x000D_ 11.B.ii. The Ortho/Para Ratio 618_x000D_ _x000D_ _x000D_ 11.B.iii. Ipso Attack 620_x000D_ _x000D_ _x000D_ 11.B.iv. Orientation in Benzene Rings with More Than One Substituent 621_x000D_ _x000D_ _x000D_ 11.B.v. Orientation in Other Ring Systems 622_x000D_ _x000D_ _x000D_ 11.C. Quantitative Treatments of Reactivity in the Substrate 624_x000D_ _x000D_ _x000D_ 11.D. A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship 626_x000D_ _x000D_ _x000D_ 11.E. The Effect of the Leaving Group 628_x000D_ _x000D_ _x000D_ 11.F. Reactions 629_x000D_ _x000D_ _x000D_ 11.F.i. Hydrogen as the Leaving Group in Simple Substitution Reactions 629_x000D_ _x000D_ _x000D_ 11.F.ii. Hydrogen as the Leaving Group in Rearrangement Reactions 675_x000D_ _x000D_ _x000D_ 11.F.iii. Other Leaving Groups 680_x000D_ _x000D_ _x000D_ 12. Aliphatic, Alkenyl, and Alkynyl Substitution: Electrophilic and Organometallic 687_x000D_ _x000D_ _x000D_ 12.A. Mechanisms 687_x000D_ _x000D_ _x000D_ 12.A.i. Bimolecular Mechanisms. SE2 and SEi 688_x000D_ _x000D_ _x000D_ 12.A.ii. The SE1 Mechanism 691_x000D_ _x000D_ _x000D_ 12.A.iii. Electrophilic Substitution Accompanied by Double-Bond Shifts 694_x000D_ _x000D_ _x000D_ 12.A.iv. Other Mechanisms 695_x000D_ _x000D_ _x000D_ 12.B. Reactivity 695_x000D_ _x000D_ _x000D_ 12.C. Reactions 697_x000D_ _x000D_ _x000D_ 12.C.i. Hydrogen as Leaving Group 697_x000D_ _x000D_ _x000D_ 12.C.ii. Metals as Leaving Groups 733_x000D_ _x000D_ _x000D_ 12.C.iii. Halogen as Leaving Group 746_x000D_ _x000D_ _x000D_ 12.C.iv. Carbon Leaving Groups 751_x000D_ _x000D_ _x000D_ 12.C.v. Electrophilic Substitution At Nitrogen 760_x000D_ _x000D_ _x000D_ 13. Aromatic Substitution: Nucleophilic and Organometallic 767_x000D_ _x000D_ _x000D_ 13.A. Mechanisms 768_x000D_ _x000D_ _x000D_ 13.A.i. The SNAr Mechanism 768_x000D_ _x000D_ _x000D_ 13.A.ii. The SN1 Mechanism 771_x000D_ _x000D_ _x000D_ 13.A.iii. The Benzyne Mechanism 772_x000D_ _x000D_ _x000D_ 13.A.iv. The SRN1 Mechanism 774_x000D_ _x000D_ _x000D_ 13.A.v. Other Mechanisms 776_x000D_ _x000D_ _x000D_ 13.B. Reactivity 776_x000D_ _x000D_ _x000D_ 13.B.i. The Effect of Substrate Structure 776_x000D_ _x000D_ _x000D_ 13.B.ii. The Effect of the Leaving Group 778_x000D_ _x000D_ _x000D_ 13.B.iii. The Effect of the Attacking Nucleophile 779_x000D_ _x000D_ _x000D_ 13.C. Reactions 779_x000D_ _x000D_ _x000D_ 13.C.i. All Leaving Groups Except Hydrogen and N2+ 779_x000D_ _x000D_ _x000D_ 13.C.ii. Hydrogen as Leaving Group 823_x000D_ _x000D_ _x000D_ 13.C.iii. Nitrogen as Leaving Group 824_x000D_ _x000D_ _x000D_ 13.C.iv. Rearrangements 834_x000D_ _x000D_ _x000D_ 14. Radical Reactions 839_x000D_ _x000D_ _x000D_ 14.A. Mechanisms 839_x000D_ _x000D_ _x000D_ 14.A.i. Radical Mechanisms in General 839_x000D_ _x000D_ _x000D_ 14.A.ii. Free-Radical Substitution Mechanisms 844_x000D_ _x000D_ _x000D_ 14.A.iii. Mechanisms at an Aromatic Substrate 845_x000D_ _x000D_ _x000D_ 14.A.iv. Neighboring-Group Assistance in Free-Radical Reactions 847_x000D_ _x000D_ _x000D_ 14.B. Reactivity 848_x000D_ _x000D_ _x000D_ 14.B.i. Reactivity for Aliphatic Substrates 848_x000D_ _x000D_ _x000D_ 14.B.ii. Reactivity at a Bridgehead 853_x000D_ _x000D_ _x000D_ 14.B.iii. Reactivity in Aromatic Substrates 854_x000D_ _x000D_ _x000D_ 14.B.iv. Reactivity in the Attacking Radical 855_x000D_ _x000D_ _x000D_ 14.B.v. The Effect of Solvent on Reactivity 856_x000D_ _x000D_ _x000D_ 14.C. Reactions 856_x000D_ _x000D_ _x000D_ 14.C.i. Hydrogen as Leaving Group 856_x000D_ _x000D_ _x000D_ 14.C.ii. Metals as Leaving Groups 880_x000D_ _x000D_ _x000D_ 14.C.iii. Halogen as Leaving Group 883_x000D_ _x000D_ _x000D_ 14.C.iv. Sulfur as Leaving Group 883_x000D_ _x000D_ _x000D_ 14.C.v. Carbon as Leaving Group 885_x000D_ _x000D_ _x000D_ 15. Addition to Carbon-Carbon Multiple Bonds 891_x000D_ _x000D_ _x000D_ 15.A. Mechanisms 892_x000D_ _x000D_ _x000D_ 15.A.i. Electrophilic Addition 892_x000D_ _x000D_ _x000D_ 15.A.ii. Nucleophilic Addition 895_x000D_ _x000D_ _x000D_ 15.A.iii. Free-Radical Addition 896_x000D_ _x000D_ _x000D_ 15.A.iv. Cyclic Mechanisms 898_x000D_ _x000D_ _x000D_ 15.A.v. Addition to Conjugated Systems 898_x000D_ _x000D_ _x000D_ 15.B. Orientation and Reactivity 899_x000D_ _x000D_ _x000D_ 15.B.i. Reactivity 899_x000D_ _x000D_ _x000D_ 15.B.ii. Orientation 902_x000D_ _x000D_ _x000D_ 15.B.iii. Stereochemical Orientation 904_x000D_ _x000D_ _x000D_ 15.B.iv. Addition to Cyclopropane Rings 906_x000D_ _x000D_ _x000D_ 15.C. Reactions 908_x000D_ _x000D_ _x000D_ 15.C.i. Isomerization of Double and Triple Bonds 908_x000D_ _x000D_ _x000D_ 15.C.ii. Reactions in Which Hydrogen Adds to One Side 910_x000D_ _x000D_ _x000D_ 15.C.iii. Reactions in Which Hydrogen Adds to Neither Side 992_x000D_ _x000D_ _x000D_ 15.C.iv. Cycloaddition Reactions 1027_x000D_ _x000D_ _x000D_ 16. Addition to Carbon-Heteroatom Multiple Bonds 1087_x000D_ _x000D_ _x000D_ 16.A. Mechanism and Reactivity 1087_x000D_ _x000D_ _x000D_ 16.A.i. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 1089_x000D_ _x000D_ _x000D_ 16.B. Reactions 1094_x000D_ _x000D_ _x000D_ 16.B.i. Reactions in Which Hydrogen or a Metallic Ion Adds to the Heteroatom 1095_x000D_ _x000D_ _x000D_ 16.B.ii. Acyl Substitution Reactions 1218_x000D_ _x000D_ _x000D_ 16.B.iii. Reactions in Which Carbon Adds to the Heteroatom 1257_x000D_ _x000D_ _x000D_ 16.B.iv. Addition to Isocyanides 1264_x000D_ _x000D_ _x000D_ 16.B.v. Nucleophilic Substitution at a Sulfonyl Sulfur Atom 1266_x000D_ _x000D_ _x000D_ 17. Elimination Reactions 1273_x000D_ _x000D_ _x000D_ 17.A. Mechanisms and Orientation 1273_x000D_ _x000D_ _x000D_ 17.A.i. The E2 Mechanism 1274_x000D_ _x000D_ _x000D_ 17.A.ii. The E1 Mechanism 1280_x000D_ _x000D_ _x000D_ 17.A.iii. The E1cB Mechanism 1281_x000D_ _x000D_ _x000D_ 17.A.iv. The E1-E2-E1cB Spectrum 1286_x000D_ _x000D_ _x000D_ 17.A.v. The E2C Mechanism 1287_x000D_ _x000D_ _x000D_ 17.B. Regiochemistry of the Double Bond 1288_x000D_ _x000D_ _x000D_ 17.C. Stereochemistry of the Double Bond 1290_x000D_ _x000D_ _x000D_ 17.D. Reactivity 1291_x000D_ _x000D_ _x000D_ 17.D.i. Effect of Substrate Structure 1291_x000D_ _x000D_ _x000D_ 17.D.ii. Effect of the Attacking Base 1293_x000D_ _x000D_ _x000D_ 17.D.iii. Effect of the Leaving Group 1294_x000D_ _x000D_ _x000D_ 17.D.iv. Effect of the Medium 1294_x000D_ _x000D_ _x000D_ 17.E. Mechanisms and Orientation in Pyrolytic Eliminations 1295_x000D_ _x000D_ _x000D_ 17.E.i. Mechanisms 1295_x000D_ _x000D_ _x000D_ 17.E.ii. Orientation in Pyrolytic Eliminations 1298_x000D_ _x000D_ _x000D_ 17.E.iii. 1,4 Conjugate Eliminations 1298_x000D_ _x000D_ _x000D_ 17.F. Reactions 1299_x000D_ _x000D_ _x000D_ 17.F.i. Reactions in Which C C and C C Bonds are Formed 1299_x000D_ _x000D_ _x000D_ 17.F.ii. Fragmentations 1321_x000D_ _x000D_ _x000D_ 17.F.iii. Reactions in Which C N or C N Bonds are Formed 1325_x000D_ _x000D_ _x000D_ 17.F.iv. Reactions in Which C O Bonds are Formed 1328_x000D_ _x000D_ _x000D_ 17.F.v. Reactions in Which N N Bonds are Formed 1329_x000D_ _x000D_ _x000D_ 17.F.vi. Extrusion Reactions 1329_x000D_ _x000D_ _x000D_ 18. Rearrangements 1335_x000D_ _x000D_ _x000D_ 18.A. Mechanisms 1336_x000D_ _x000D_ _x000D_ 18.A.i. Nucleophilic Rearrangements 1336_x000D_ _x000D_ _x000D_ 18.A.ii. The Actual Nature of the Migration 1337_x000D_ _x000D_ _x000D_ 18.A.iii. Migratory Aptitudes 1340_x000D_ _x000D_ _x000D_ 18.A.iv. Memory Effects 1343_x000D_ _x000D_ _x000D_ 18.B. Longer Nucleophilic Rearrangements 1344_x000D_ _x000D_ _x000D_ 18.C. Free-Radical Rearrangements 1345_x000D_ _x000D_ _x000D_ 18.D. Carbene Rearrangements 1349_x000D_ _x000D_ _x000D_ 18.E. Electrophilic Rearrangements 1349_x000D_ _x000D_ _x000D_ 18.F. Reactions 1350_x000D_ _x000D_ _x000D_ 18.F.i. 1,2-Rearrangements 1350_x000D_ _x000D_ _x000D_ 18.F.ii. Non 1,2-Rearrangements 1389_x000D_ _x000D_ _x000D_ 19. Oxidations and Reductions 1439_x000D_ _x000D_ _x000D_ 19.A. Mechanisms 1440_x000D_ _x000D_ _x000D_ 19.B. Reactions 1442_x000D_ _x000D_ _x000D_ 19.B.i. Oxidations 1442_x000D_ _x000D_ _x000D_ 19.B.ii. Reductions 1510_x000D_ _x000D_ _x000D_ Appendix A: The Literature of Organic Chemistry 1607_x000D_ _x000D_ _x000D_ Appendix B: Classification of Reactions by Type of Compounds Synthesized 1645_x000D_ _x000D_ _x000D_ Indexes_x000D_ _x000D_ _x000D_ Author Index 1669_x000D_ _x000D_ _x000D_ Subject Index 1917_x000D_ show more