{"product_id":"marchs-advanced-organic-chemistry-isbn-9781394242993","title":"March's Advanced Organic Chemistry","description":"\u003cp\u003e\u003cb\u003eLeading reference on the theories of organic chemistry, now updated to reflect the most recent literature from 2018 to 2023\u003c\/b\u003e \u003c\/p\u003e\u003cp\u003eBuilding on the success of the 8th Edition as winner of the Textbook \u0026amp; Academic Authors Association 2021 McGuffey Longevity Award, the revised and updated 9th Edition of \u003ci\u003eMarch’s Advanced Organic Chemistry\u003c\/i\u003eexplains the theories of organic chemistry, covers new advances in areas of organic chemistry published between 2018 and 2023, and guides readers to plan and execute multi-step synthetic reactions. Detailed examples and descriptions of all reactions are included throughout the text. \u003c\/p\u003e\u003cp\u003eAs in previous editions, the goal of this edition is to give equal weight to three fundamental aspects of the study of organic chemistry: reactions, mechanisms, and structure. Specific but specialized areas of organic chemistry, such as terpenes, polymerization, and steroids, have been incorporated into primary sections rather than segregated into their own sections. \u003c\/p\u003e\u003cp\u003eThe first nine chapters cover general organic chemistry with theoretical principles. The next 10 chapters address reactions and mechanistic discussion. Appendix A focuses on literature references and resources. More than 4,400 references are included throughout the text. \u003c\/p\u003e\u003cp\u003e\u003ci\u003eMarch’s Advanced Organic Chemistry \u003c\/i\u003eprovides information on: \u003c\/p\u003e\u003cul\u003e\n\u003cli\u003eLocalized and delocalized chemical bonding and bonding weaker than covalent\u003c\/li\u003e\n\u003cli\u003eMicrowave chemistry, use of ultrasound, mechanochemistry, and reactions done under flow conditions\u003c\/li\u003e\n\u003cli\u003eAcids and bases, irradiation processes, stereochemistry, structure of intermediates, and ordinary and photochemical reactions\u003c\/li\u003e\n\u003cli\u003eMechanisms and methods of determining carbocations, carbanions, free radicals, carbenes, and nitrenes\u003c\/li\u003e\n\u003cli\u003eAliphatic, alkenyl, and alkynyl substitution, additions to carbon-carbon and carbon-hetero bonds, eliminations, rearrangements, and oxidations and reductions\u003c\/li\u003e\n\u003c\/ul\u003e \u003cp\u003eThis 9th Edition of \u003ci\u003eMarch’s Advanced Organic Chemistry\u003c\/i\u003e continues to serve as a must-have reference for every student and professional working in organic chemistry or related fields. \u003c\/p\u003e\u003cp\u003eNew Reaction Sections Correlation: 8th Edition → 9th Editions xiii\u003c\/p\u003e \u003cp\u003ePreface xix\u003c\/p\u003e \u003cp\u003eCommon Abbreviations xxi\u003c\/p\u003e \u003cp\u003eBiographical Statement xxvii\u003c\/p\u003e \u003cp\u003eNew Features of the 9th Edition xxix\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart I Introduction 1\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e1. Localized Chemical Bonding 3\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e1.a. Covalent Bonding 3\u003c\/p\u003e \u003cp\u003e1.b. Multiple Valence 6\u003c\/p\u003e \u003cp\u003e1.c. Hybridization 6\u003c\/p\u003e \u003cp\u003e1.d. Multiple Bonds 7\u003c\/p\u003e \u003cp\u003e1.e. Photoelectron Spectroscopy 9\u003c\/p\u003e \u003cp\u003e1.f. Electronic Structures of Molecules 11\u003c\/p\u003e \u003cp\u003e1.g. Electronegativity 13\u003c\/p\u003e \u003cp\u003e1.h. Dipole Moment 15\u003c\/p\u003e \u003cp\u003e1.i. Inductive and Field Effects 16\u003c\/p\u003e \u003cp\u003e1.j. Bond Distances 19\u003c\/p\u003e \u003cp\u003e1.k. Bond Angles 22\u003c\/p\u003e \u003cp\u003e1.l. Bond Energies 23\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2. Delocalized Chemical Bonding 27\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e2.a. Molecular Orbitals 28\u003c\/p\u003e \u003cp\u003e2.b. Bond Energies and Distances in Compounds Containing Delocalized Bonds 31\u003c\/p\u003e \u003cp\u003e2.c. Molecules that have Delocalized Bonds 32\u003c\/p\u003e \u003cp\u003e2.d. Cross- Conjugation 35\u003c\/p\u003e \u003cp\u003e2.e. The Rules of Resonance 36\u003c\/p\u003e \u003cp\u003e2.f. The Resonance Effect 37\u003c\/p\u003e \u003cp\u003e2.g. Steric Inhibition of Resonance and the Influences of Strain 37\u003c\/p\u003e \u003cp\u003e2.h. pπ–dπ Bonding. Ylids 40\u003c\/p\u003e \u003cp\u003e2.i. Aromaticity 42\u003c\/p\u003e \u003cp\u003e2.I.i. Six- Membered Rings 45\u003c\/p\u003e \u003cp\u003e2.I.ii. Five- , Seven- , and Eight- Membered Rings 48\u003c\/p\u003e \u003cp\u003e2.I.iii. Other Systems Containing Aromatic Sextets 52\u003c\/p\u003e \u003cp\u003e2.j. Alternant and Nonalternant Hydrocarbons 54\u003c\/p\u003e \u003cp\u003e2.k. Aromatic Systems with Electron Numbers other than Six 54\u003c\/p\u003e \u003cp\u003e2.K.i. Systems of Two Electrons 55\u003c\/p\u003e \u003cp\u003e2.K.ii. Systems of Four Electrons: Antiaromaticity 56\u003c\/p\u003e \u003cp\u003e2.K.iii. Systems of Eight Electrons 59\u003c\/p\u003e \u003cp\u003e2.K.iv. Systems of Ten Electrons 60\u003c\/p\u003e \u003cp\u003e2.K.v. Systems of More than Ten Electrons: 4n + 2 Electrons 62\u003c\/p\u003e \u003cp\u003e2.K.vi. Systems of More than Ten Electrons: 4n Electrons 66\u003c\/p\u003e \u003cp\u003e2.l. Other Aromatic Compounds 70\u003c\/p\u003e \u003cp\u003e2.M. Hyperconjugation 72\u003c\/p\u003e \u003cp\u003e2.n. Tautomerism 75\u003c\/p\u003e \u003cp\u003e2.N.i. Keto- Enol Tautomerism 75\u003c\/p\u003e \u003cp\u003e2.N.ii. Other Proton- Shift Tautomerism 79\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3. Bonding Weaker Than Covalent 83\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e3.a. Hydrogen Bonding 83\u003c\/p\u003e \u003cp\u003e3.b. π–π Interactions 90\u003c\/p\u003e \u003cp\u003e3.c. Addition Compounds 91\u003c\/p\u003e \u003cp\u003e3.C.i. Electron Donor–Acceptor Complexes 92\u003c\/p\u003e \u003cp\u003e3.C.ii. Crown Ether Complexes and Cryptates 94\u003c\/p\u003e \u003cp\u003e3.C.iii. Inclusion Compounds 99\u003c\/p\u003e \u003cp\u003e3.C.iv. Cyclodextrins 102\u003c\/p\u003e \u003cp\u003e3.d. Catenanes and Rotaxanes 104\u003c\/p\u003e \u003cp\u003e3.e. Cucurbit[n]Uril- Based Gyroscane 107\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4. Stereochemistry and Conformation 109\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e4.a. Optical Activity and Chirality 109\u003c\/p\u003e \u003cp\u003e4.b. Dependence of Rotation on Conditions of Measurement 111\u003c\/p\u003e \u003cp\u003e4.c. What kinds of Molecules Display Optical Activity? 112\u003c\/p\u003e \u003cp\u003e4.d. The Fischer Projection 121\u003c\/p\u003e \u003cp\u003e4.e. Absolute Configuration 121\u003c\/p\u003e \u003cp\u003e4.E.i. The Cahn–Ingold–Prelog System 122\u003c\/p\u003e \u003cp\u003e4.E.ii. Methods of Determining Configuration 125\u003c\/p\u003e \u003cp\u003e4.f. Optical Purity 128\u003c\/p\u003e \u003cp\u003e4.g. The Cause of Optical Activity 130\u003c\/p\u003e \u003cp\u003e4.h. Molecules with more than One Stereogenic Center 131\u003c\/p\u003e \u003cp\u003e4.i. Asymmetric Synthesis 134\u003c\/p\u003e \u003cp\u003e4.j. Methods of Resolution 137\u003c\/p\u003e \u003cp\u003e4.k. Cis–Trans Isomerism 142\u003c\/p\u003e \u003cp\u003e4.K.i. Cis–Trans Isomerism Resulting from Double Bonds 142\u003c\/p\u003e \u003cp\u003e4.K.ii. Cis–Trans Isomerism of Monocyclic Compounds 145\u003c\/p\u003e \u003cp\u003e4.K.iii. Cis–Trans Isomerism of Fused and Bridged Ring Systems 146\u003c\/p\u003e \u003cp\u003e4.l. Out–In Isomerism 147\u003c\/p\u003e \u003cp\u003e4.M. Enantiotopic and Diastereotopic Atoms, Groups, and Faces 149\u003c\/p\u003e \u003cp\u003e4.n. Stereospecific and Stereoselective Syntheses 151\u003c\/p\u003e \u003cp\u003e4.o. Conformational Analysis 152\u003c\/p\u003e \u003cp\u003e4.O.i. Conformation in Open- Chain Systems 153\u003c\/p\u003e \u003cp\u003e4.O.ii. Conformation in Six- Membered Rings 158\u003c\/p\u003e \u003cp\u003e4.O.iii. Conformation in Six- Membered Rings Containing Heteroatoms 162\u003c\/p\u003e \u003cp\u003e4.O.iv. Conformation in Other Rings 164\u003c\/p\u003e \u003cp\u003e4.p. Molecular Mechanics 166\u003c\/p\u003e \u003cp\u003e4.q. Strain 168\u003c\/p\u003e \u003cp\u003e4.Q.i. Strain in Small Rings 168\u003c\/p\u003e \u003cp\u003e4.Q.ii. Strain in Other Rings 172\u003c\/p\u003e \u003cp\u003e4.Q.iii. Unsaturated Rings 174\u003c\/p\u003e \u003cp\u003e4.Q.iv. Strain Due to Unavoidable Crowding 177\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5. Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes 181\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e5.a. Carbocations 182\u003c\/p\u003e \u003cp\u003e5.A.i. Nomenclature 182\u003c\/p\u003e \u003cp\u003e5.A.ii. Stability and Structure of Carbocations 182\u003c\/p\u003e \u003cp\u003e5.A.iii. The Generation and Fate of Carbocations 190\u003c\/p\u003e \u003cp\u003e5.b. Carbanions 192\u003c\/p\u003e \u003cp\u003e5.B.i. Stability and Structure 192\u003c\/p\u003e \u003cp\u003e5.B.ii. The Structure of Grignard Reagents and Organolithium Reagents 198\u003c\/p\u003e \u003cp\u003e5.B.iii. The Generation and Fate of Carbanions 201\u003c\/p\u003e \u003cp\u003e5.c. Free Radicals 202\u003c\/p\u003e \u003cp\u003e5.C.i. Stability and Structure 202\u003c\/p\u003e \u003cp\u003e5.C.ii. The Generation and Fate of Free Radicals 212\u003c\/p\u003e \u003cp\u003e5.C.iii. Radical Ions 215\u003c\/p\u003e \u003cp\u003e5.d. Carbenes 217\u003c\/p\u003e \u003cp\u003e5.D.i. Stability and Structure 217\u003c\/p\u003e \u003cp\u003e5.D.ii. The Generation and Fate of Carbenes 220\u003c\/p\u003e \u003cp\u003e5.D.iii. N- Heterocyclic Carbenes 223\u003c\/p\u003e \u003cp\u003e5.e. Nitrenes 225\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6. Mechanisms and Methods of Determining Them 229\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e6.a. Types of Mechanism 229\u003c\/p\u003e \u003cp\u003e6.b. Types of Reaction 230\u003c\/p\u003e \u003cp\u003e6.c. Thermodynamic Requirements for Reaction 232\u003c\/p\u003e \u003cp\u003e6.d. Kinetic Requirements for Reaction 233\u003c\/p\u003e \u003cp\u003e6.e. The Baldwin Rules for Ring Closure 236\u003c\/p\u003e \u003cp\u003e6.f. Kinetic and Thermodynamic Control 238\u003c\/p\u003e \u003cp\u003e6.g. The Hammond Postulate 238\u003c\/p\u003e \u003cp\u003e6.h. Microscopic Reversibility 239\u003c\/p\u003e \u003cp\u003e6.i. Marcus Theory 239\u003c\/p\u003e \u003cp\u003e6.j. Methods of Determining Mechanisms 240\u003c\/p\u003e \u003cp\u003e6.J.i. Identification of Products 241\u003c\/p\u003e \u003cp\u003e6.J.ii. Determination of the Presence of an Intermediate 241\u003c\/p\u003e \u003cp\u003e6.J.iii. The Study of Catalysis 242\u003c\/p\u003e \u003cp\u003e6.J.iv. Isotopic Labeling 243\u003c\/p\u003e \u003cp\u003e6.J.v. Stereochemical Evidence 243\u003c\/p\u003e \u003cp\u003e6.J.vi. Kinetic Evidence 244\u003c\/p\u003e \u003cp\u003e6.J.vii. Isotope Effects 250\u003c\/p\u003e \u003cp\u003e6.k. Catalyst Development 253\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7. Irradiation Processes and Techniques that Influence Reactions in Organic Chemistry 257\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e7.a. Photochemistry 257\u003c\/p\u003e \u003cp\u003e7.A.i. Excited States and the Ground State 257\u003c\/p\u003e \u003cp\u003e7.A.ii. Singlet and Triplet States: “Forbidden” Transitions 259\u003c\/p\u003e \u003cp\u003e7.A.iii. Types of Excitation 260\u003c\/p\u003e \u003cp\u003e7.A.iv. Nomenclature and Properties of Excited States 262\u003c\/p\u003e \u003cp\u003e7.A.v. Photolytic Cleavage 262\u003c\/p\u003e \u003cp\u003e7.A.vi. The Fate of the Excited Molecule: Physical Processes 263\u003c\/p\u003e \u003cp\u003e7.A.vii. The Fate of the Excited Molecule: Chemical Processes 267\u003c\/p\u003e \u003cp\u003e7.A.viii. The Determination of Photochemical Mechanisms 271\u003c\/p\u003e \u003cp\u003e7.b. Sonochemistry 272\u003c\/p\u003e \u003cp\u003e7.c. Microwave Chemistry 274\u003c\/p\u003e \u003cp\u003e7.d. Flow Chemistry 275\u003c\/p\u003e \u003cp\u003e7.e. Mechanochemistry 276\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8. Acids and Bases 279\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e8.a. Brønsted Theory 279\u003c\/p\u003e \u003cp\u003e8.A.i. Brønsted Acids 280\u003c\/p\u003e \u003cp\u003e8.A.ii. Brønsted Bases 286\u003c\/p\u003e \u003cp\u003e8.b. The Mechanism of Proton Transfer Reactions 289\u003c\/p\u003e \u003cp\u003e8.c. Measurements of Solvent Acidity 290\u003c\/p\u003e \u003cp\u003e8.d. Acid and Base Catalysis 293\u003c\/p\u003e \u003cp\u003e8.e. Lewis Acids and Bases 295\u003c\/p\u003e \u003cp\u003e8.E.i. Hard–Soft Acids–Bases 296\u003c\/p\u003e \u003cp\u003e8.f. The Effects of Structure on the Strengths of Acids and Bases 298\u003c\/p\u003e \u003cp\u003e8.g. The Effects of the Medium on Acid and Base Strength 306\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9. Effects of Structure and Medium on Reactivity 309\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e9.a. Resonance and Field Effects 309\u003c\/p\u003e \u003cp\u003e9.b. Steric Effects 311\u003c\/p\u003e \u003cp\u003e9.c. Quantitative Treatments of the Effect of Structure on Reactivity 313\u003c\/p\u003e \u003cp\u003e9.d. Effect of Medium on Reactivity and Rate 320\u003c\/p\u003e \u003cp\u003e9.e. High Pressure 321\u003c\/p\u003e \u003cp\u003e9.f. Water and other Nonorganic Solvents 321\u003c\/p\u003e \u003cp\u003e9.g. Ionic Liquid Solvents 323\u003c\/p\u003e \u003cp\u003e9.h. Solventless Reactions 325\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePart II Introduction 327\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10. Aliphatic Substitution: Nucleophilic and Organometallic 329\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e10.A. Mechanisms 330\u003c\/p\u003e \u003cp\u003e10.A.i. The S N 2 Mechanism 330\u003c\/p\u003e \u003cp\u003e10.A.ii. The S N 1 Mechanism 334\u003c\/p\u003e \u003cp\u003e10.A.iii. Ion Pairs in the S N 1 Mechanism 338\u003c\/p\u003e \u003cp\u003e10.A.iv. Mixed S N 1 and S N 2 Mechanisms 340\u003c\/p\u003e \u003cp\u003e10.B. Set Mechanisms 342\u003c\/p\u003e \u003cp\u003e10.C. The Neighboring- Group Mechanism 344\u003c\/p\u003e \u003cp\u003e10.C.i. Neighboring- Group Participation by π and σ Bonds: Nonclassical Carbocations 347\u003c\/p\u003e \u003cp\u003e10.D. The S N I Mechanism 359\u003c\/p\u003e \u003cp\u003e10.E. Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements 360\u003c\/p\u003e \u003cp\u003e10.F. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 363\u003c\/p\u003e \u003cp\u003e10.G. Reactivity 366\u003c\/p\u003e \u003cp\u003e10.G.i. The Effect of Substrate Structure 366\u003c\/p\u003e \u003cp\u003e10.G.ii. The Effect of the Attacking Nucleophile 374\u003c\/p\u003e \u003cp\u003e10.G.iii. The Effect of the Leaving Group 378\u003c\/p\u003e \u003cp\u003e10.G.iv. The Effect of the Reaction Medium 382\u003c\/p\u003e \u003cp\u003e10.G.v. Phase- Transfer Catalysis 387\u003c\/p\u003e \u003cp\u003e10.G.vi. Influencing Reactivity by External Means 389\u003c\/p\u003e \u003cp\u003e10.G.vii. Ambident (Bidentant) Nucleophiles: Regioselectivity 390\u003c\/p\u003e \u003cp\u003e10.G.viii. Ambident Substrates 393\u003c\/p\u003e \u003cp\u003e10.H. Reactions 394\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11. Aromatic Substitution: Electrophilic 491\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e11.A. Mechanisms 491\u003c\/p\u003e \u003cp\u003e11.A.i. The Arenium Ion Mechanism 491\u003c\/p\u003e \u003cp\u003e11.B. Orientation and Reactivity 496\u003c\/p\u003e \u003cp\u003e11.B.i. Orientation and Reactivity in Monosubstituted Benzene Rings 496\u003c\/p\u003e \u003cp\u003e11.B.ii. The Ortho\/Para Ratio 499\u003c\/p\u003e \u003cp\u003e11.B.iii. Ipso Attack 500\u003c\/p\u003e \u003cp\u003e11.B.iv. Orientation in Benzene Rings with more than one Substituent 501\u003c\/p\u003e \u003cp\u003e11.B.v. Orientation in Other Ring Systems 502\u003c\/p\u003e \u003cp\u003e11.C. Quantitative Treatments of Reactivity in the Substrate 504\u003c\/p\u003e \u003cp\u003e11.D. A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship 505\u003c\/p\u003e \u003cp\u003e11.E. The Effect of the Leaving Group 507\u003c\/p\u003e \u003cp\u003e11.F. Reactions 507\u003c\/p\u003e \u003cp\u003e\u003cb\u003e12. Aliphatic, Alkenyl, and Alkynyl Substitution: Electrophilic and Organometallic 555\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e12.A. Mechanisms 555\u003c\/p\u003e \u003cp\u003e12.A.i. Bimolecular Mechanisms: S E 2 and S E I 556\u003c\/p\u003e \u003cp\u003e12.A.ii. The S E 1 Mechanism 558\u003c\/p\u003e \u003cp\u003e12.A.iii. Electrophilic Substitution Accompanied by Double- Bond Shifts 560\u003c\/p\u003e \u003cp\u003e12.A.iv. Other Mechanisms 561\u003c\/p\u003e \u003cp\u003e12.B. Reactivity 561\u003c\/p\u003e \u003cp\u003e12.C. Reactions 562\u003c\/p\u003e \u003cp\u003e\u003cb\u003e13. Aromatic Substitution: Nucleophilic and Organometallic 617\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e13.A. Mechanisms 617\u003c\/p\u003e \u003cp\u003e13.A.i. The S N Ar Mechanism 618\u003c\/p\u003e \u003cp\u003e13.A.ii. The S N 1 Mechanism 620\u003c\/p\u003e \u003cp\u003e13.A.iii. The Benzyne Mechanism 621\u003c\/p\u003e \u003cp\u003e13.A.iv. The S RN 1 Mechanism 623\u003c\/p\u003e \u003cp\u003e13.A.v. Other Mechanisms 624\u003c\/p\u003e \u003cp\u003e13.B. Reactivity 625\u003c\/p\u003e \u003cp\u003e13.B.i. The Effect of Substrate Structure 625\u003c\/p\u003e \u003cp\u003e13.B.ii. The Effect of the Leaving Group 626\u003c\/p\u003e \u003cp\u003e13.B.iii. The Effect of the Attacking Nucleophile 626\u003c\/p\u003e \u003cp\u003e13.C. Reactions 627\u003c\/p\u003e \u003cp\u003e\u003cb\u003e14. Radical Reactions 677\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e14.A. Mechanisms 677\u003c\/p\u003e \u003cp\u003e14.A.i. Radical Mechanisms in General 677\u003c\/p\u003e \u003cp\u003e14.A.ii. Free- Radical Substitution Mechanisms 681\u003c\/p\u003e \u003cp\u003e14.A.iii. Mechanisms at an Aromatic Substrate 682\u003c\/p\u003e \u003cp\u003e14.A.iv. Neighboring- Group Assistance in Free- Radical Reactions 683\u003c\/p\u003e \u003cp\u003e14.B. Reactivity 684\u003c\/p\u003e \u003cp\u003e14.B.i. Reactivity for Aliphatic Substrates 684\u003c\/p\u003e \u003cp\u003e14.B.ii. Reactivity at a Bridgehead 688\u003c\/p\u003e \u003cp\u003e14.B.iii. Reactivity in Aromatic Substrates 689\u003c\/p\u003e \u003cp\u003e14.B.iv. Reactivity in the Attacking Radical 690\u003c\/p\u003e \u003cp\u003e14.B.v. The Effect of Solvent on Reactivity 690\u003c\/p\u003e \u003cp\u003e14.C. Reactions 691\u003c\/p\u003e \u003cp\u003e\u003cb\u003e15. Addition to Carbon–Carbon Multiple Bonds 717\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e15.A. Mechanisms 717\u003c\/p\u003e \u003cp\u003e15.A.i. Electrophilic Addition 717\u003c\/p\u003e \u003cp\u003e15.A.ii. Nucleophilic Addition 719\u003c\/p\u003e \u003cp\u003e15.A.iii. Free- Radical Addition 720\u003c\/p\u003e \u003cp\u003e15.A.iv. Cyclic Mechanisms 722\u003c\/p\u003e \u003cp\u003e15.A.v. Addition to Conjugated Systems 722\u003c\/p\u003e \u003cp\u003e15.B. Orientation and Reactivity 722\u003c\/p\u003e \u003cp\u003e15.B.i. Reactivity 722\u003c\/p\u003e \u003cp\u003e15.B.ii. Orientation 725\u003c\/p\u003e \u003cp\u003e15.B.iii. Stereochemical Orientation 727\u003c\/p\u003e \u003cp\u003e15.B.iv. Addition to Cyclopropane Rings 728\u003c\/p\u003e \u003cp\u003e15.C. Reactions 729\u003c\/p\u003e \u003cp\u003e\u003cb\u003e16. Addition to Carbon–Heteroatom Multiple Bonds 869\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e16.A. Mechanism and Reactivity 869\u003c\/p\u003e \u003cp\u003e16.A.i. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism 871\u003c\/p\u003e \u003cp\u003e16.B. Reactions 874\u003c\/p\u003e \u003cp\u003e\u003cb\u003e17. Elimination Reactions 1001\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e17.A. Mechanisms and Orientation 1001\u003c\/p\u003e \u003cp\u003e17.A.i. The E2 Mechanism 1002\u003c\/p\u003e \u003cp\u003e17.A.ii. The E1 Mechanism 1006\u003c\/p\u003e \u003cp\u003e17.A.iii. The E1cB Mechanism 1007\u003c\/p\u003e \u003cp\u003e17.A.iv. The E1–E2–E1cB Spectrum 1011\u003c\/p\u003e \u003cp\u003e17.A.v. The E2C Mechanism 1012\u003c\/p\u003e \u003cp\u003e17.B. Regiochemistry of the Double Bond 1013\u003c\/p\u003e \u003cp\u003e17.C. Stereochemistry of the Double Bond 1014\u003c\/p\u003e \u003cp\u003e17.D. Reactivity 1015\u003c\/p\u003e \u003cp\u003e17.D.i. Effect of Substrate Structure 1015\u003c\/p\u003e \u003cp\u003e17.D.ii. Effect of the Attacking Base 1017\u003c\/p\u003e \u003cp\u003e17.D.iii. Influence of the Leaving Group 1017\u003c\/p\u003e \u003cp\u003e17.D.iv. Influence of the Medium 1018\u003c\/p\u003e \u003cp\u003e17.E. Mechanisms and Orientation in Pyrolytic Eliminations 1018\u003c\/p\u003e \u003cp\u003e17.E.i. Mechanisms 1018\u003c\/p\u003e \u003cp\u003e17.E.ii. Orientation in Pyrolytic Eliminations 1020\u003c\/p\u003e \u003cp\u003e17.F. Reactions 1021\u003c\/p\u003e \u003cp\u003e\u003cb\u003e18. Rearrangements 1047\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e18.A. Mechanisms 1048\u003c\/p\u003e \u003cp\u003e18.A.i. Nucleophilic Rearrangements 1048\u003c\/p\u003e \u003cp\u003e18.A.ii. The Actual Nature of the Migration 1049\u003c\/p\u003e \u003cp\u003e18.A.iii. Migratory Aptitudes 1051\u003c\/p\u003e \u003cp\u003e18.A.iv. Memory Effects 1052\u003c\/p\u003e \u003cp\u003e18.B. Longer Nucleophilic Rearrangements 1053\u003c\/p\u003e \u003cp\u003e18.C. Free- Radical Rearrangements 1054\u003c\/p\u003e \u003cp\u003e18.D. Carbene Rearrangements 1057\u003c\/p\u003e \u003cp\u003e18.E. Electrophilic Rearrangements 1057\u003c\/p\u003e \u003cp\u003e18.F. Reactions 1057\u003c\/p\u003e \u003cp\u003e\u003cb\u003e19. Oxidations and Reductions 1123\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e19.A. Mechanisms 1125\u003c\/p\u003e \u003cp\u003e19.B. Reactions 1126\u003c\/p\u003e \u003cp\u003e19.B.i. Oxidations 1126\u003c\/p\u003e \u003cp\u003e19.B.ii. Reductions 1172\u003c\/p\u003e \u003cp\u003eAppendix A: the Literature of Organic Chemistry 1243\u003c\/p\u003e \u003cp\u003eIndexes 1273\u003c\/p\u003e \u003cp\u003eAuthor Index 1273\u003c\/p\u003e \u003cp\u003eSubject Index 1501\u003c\/p\u003e  \u003cp\u003e\u003cb\u003eMichael B. Smith, PhD,\u003c\/b\u003e is Professor Emeritus in the Department of Chemistry at the University of Connecticut. He is a coauthor of the fifth through eighth editions of \u003ci\u003eMarch’s Advanced Organic Chemistry\u003c\/i\u003e and the author of Volumes 6 - 13 of the \u003ci\u003eCompendium of Organic Synthetic Methods\u003c\/i\u003e, as well as several other monographs and textbooks.   \u003c\/p\u003e\u003cp\u003e\u003cb\u003eLeading reference on the theories of organic chemistry, now updated to reflect the most recent literature from 2018 to 2023\u003c\/b\u003e \u003c\/p\u003e\u003cp\u003eBuilding on the success of the 8th Edition as winner of the Textbook \u0026amp; Academic Authors Association 2021 McGuffey Longevity Award, the revised and updated 9th Edition of \u003ci\u003eMarch’s Advanced Organic Chemistry\u003c\/i\u003eexplains the theories of organic chemistry, covers new advances in areas of organic chemistry published between 2018 and 2023, and guides readers to plan and execute multi-step synthetic reactions. Detailed examples and descriptions of all reactions are included throughout the text. \u003c\/p\u003e\u003cp\u003eAs in previous editions, the goal of this edition is to give equal weight to three fundamental aspects of the study of organic chemistry: reactions, mechanisms, and structure. Specific but specialized areas of organic chemistry, such as terpenes, polymerization, and steroids, have been incorporated into primary sections rather than segregated into their own sections. \u003c\/p\u003e\u003cp\u003eThe first nine chapters cover general organic chemistry with theoretical principles. The next 10 chapters address reactions and mechanistic discussion. Appendix A focuses on literature references and resources. More than 4,400 references are included throughout the text. \u003c\/p\u003e\u003cp\u003e\u003ci\u003eMarch’s Advanced Organic Chemistry \u003c\/i\u003eprovides information on: \u003c\/p\u003e\u003cul\u003e\n\u003cli\u003eLocalized and delocalized chemical bonding and bonding weaker than covalent\u003c\/li\u003e\n\u003cli\u003eMicrowave chemistry, use of ultrasound, mechanochemistry, and reactions done under flow conditions\u003c\/li\u003e\n\u003cli\u003eAcids and bases, irradiation processes, stereochemistry, structure of intermediates, and ordinary and photochemical reactions\u003c\/li\u003e\n\u003cli\u003eMechanisms and methods of determining carbocations, carbanions, free radicals, carbenes, and nitrenes\u003c\/li\u003e\n\u003cli\u003eAliphatic, alkenyl, and alkynyl substitution, additions to carbon-carbon and carbon-hetero bonds, eliminations, rearrangements, and oxidations and reductions\u003c\/li\u003e\n\u003c\/ul\u003e \u003cp\u003eThis 9th Edition of \u003ci\u003eMarch’s Advanced Organic Chemistry\u003c\/i\u003e continues to serve as a must-have reference for every student and professional working in organic chemistry or related fields.\u003c\/p\u003e","brand":"Wiley","offers":[{"title":"Default Title","offer_id":47989572370661,"sku":"NP9781394242993","price":143.5,"currency_code":"USD","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/1842\/7735\/files\/9781394242993.jpg?v=1761784649","url":"https:\/\/k12savings.com\/products\/marchs-advanced-organic-chemistry-isbn-9781394242993","provider":"K12savings","version":"1.0","type":"link"}