Steffen Berg and Abhik Ghosh are chemists based at UiT – The Arctic University of Norway. They share a passion for chemical education, and are particularly interested in developing methods to help high school students and undergraduates understand difficult concepts.

• Foreword xiPreface xiiiAcknowledgments xvii1. A Collection of Basic Concepts 11.1 Nucleophiles and Electrophiles: The SN2 Paradigm 21.2 What Makes for a Good Nucleophile? 51.3 Hard and Soft Acids and Bases: The HSAB Principle 81.4 pKa Values: What Makes for a Good Leaving Group? 91.5 Redox Potentials 111.6 Thermodynamic Control: Bond Dissociation Energies (BDEs) 111.7 Bimolecular β-Elimination (E2) 141.8 Proton Transfers (PTs) 151.9 Elementary Associative and Dissociative Processes (A and D) 161.10 Two-Step Ionic Mechanisms: The SN2-Si Pathway 191.11 Two-Step Ionic Mechanisms: The SN1 and E1 Pathways 201.12 Electrophilic Addition to Carbon–Carbon Multiple Bonds 221.13 Electrophilic Substitution on Aromatics: Addition–Elimination 231.14 Nucleophilic Addition to Carbon–Heteroatom Multiple Bonds 241.15 Carbanions and Related Synthetic Intermediates 261.16 Carbenes 291.17 Oxidative Additions and Reductive Eliminations 301.18 Migrations 321.19 Ligand Exchange Reactions 331.20 Radical Reactions 351.21 Pericyclic Reactions 371.22 Arrow Pushing: Organic Paradigms 381.23 Inorganic Arrow Pushing: Thinking Like a Lone Pair 381.24 Definitions: Valence, Oxidation State, Formal Charge, and Coordination Number 401.25 Elements of Bonding in Hypervalent Compounds 411.26 The λ Convention 451.27 The Inert Pair Effect 461.28 Summary 47Further Reading 482. The s-Block Elements: Alkali and Alkaline Earth Metals 502.1 Solubility 512.2 The s-Block Metals as Reducing Agents 522.3 Reductive Couplings 532.4 Dissolving Metal Reactions 562.5 Organolithium and Organomagnesium Compounds 582.6 Dihydrogen Activation by Frustrated Lewis Pairs (FLPs) 612.7 A MgI –MgI Bond 632.8 Summary 64Further Reading 653. Group 13 Elements 663.1 Group 13 Compounds as Lewis Acids 673.2 Hydroboration 703.3 Group 13-Based Reducing Agents 733.4 From Borazine to Gallium Arsenide: 13–15 Compounds 763.5 Low-Oxidation-State Compounds 803.6 The Boryl Anion 873.7 Indium-Mediated Allylations 883.8 Thallium Reagents 893.9 Summary 94Further Reading 944. Group 14 Elements 964.1 Silyl Protecting Groups 984.2 A Case Study: Peterson Olefination 1034.3 Silanes 1044.4 The β-Silicon Effect: Allylsilanes 1064.5 Silyl Anions 1094.6 Organostannanes 1124.7 Polystannanes 1134.8∗ Carbene and Alkene Analogs 1154.9∗ Alkyne Analogs 1204.10 Silyl Cations 1224.11 Glycol Cleavage by Lead Tetraacetate 1244.12 Summary 127Further Reading 1285A. Nitrogen 1295A.1 Ammonia and Some Other Common Nitrogen Nucleophiles 1305A.2 Some Common Nitrogen Electrophiles: Oxides, Oxoacids, and Oxoanions 1315A.3 N–N Bonded Molecules: Synthesis of Hydrazine 1335A.4 Multiple Bond Formation: Synthesis of Sodium Azide 1355A.5 Thermal Decomposition of NH4NO 2 and NH4NO 3 1375A.6 Diazonium Salts 1385A.7 Azo Compounds and Diazene 1405A.8 ∗ Imines and Related Functional Groups: The Wolff–Kishner Reduction and the Shapiro Reaction 1445A.9 Diazo Compounds 1465A.10 Nitrenes and Nitrenoids: The Curtius Rearrangement 1495A.11 Nitric Oxide and Nitrogen Dioxide 1515A.12 Summary 155Further Reading 1555B. The Heavier Pnictogens 1565B.1 Oxides 1585B.2 Halides and Oxohalides 1605B.3 Phosphorus in Biology: Why Nature Chose Phosphate 1635B.4 Arsenic-Based DNA 1665B.5 Arsenic Toxicity and Biomethylation 1685B.6 Alkali-Induced Disproportionation of Phosphorus 1715B.7 Disproportionation of Hypophosphorous Acid 1735B.8 The Arbuzov Reaction 1755B.9 The Wittig and Related Reactions: Phosphorus Ylides 1765B.10 Phosphazenes 1805B.11∗ The Corey–Winter Olefination 1855B.12 Triphenylphosphine-Mediated Halogenations 1875B.13∗ The Mitsunobu Reaction 1885B.14∗ The Vilsmeier–Haack Reaction 1915B.15 SbF5 and Superacids 1935B.16 Bismuth in Organic Synthesis: Green Chemistry 1955B.17 Summary 200Further Reading 2006. Group 16 Elements: The Chalcogens 2026.1 The Divalent State: Focus on Sulfur 2046.2 The Divalent State: Hydrogen Peroxide 2056.3 S2Cl2 and SCl2 2096.4 Nucleophilic Breakdown of Cyclopolysulfur Rings 2116.5 Cyclooctachalcogen Ring Formation 2136.6 Higher-Valent States: Oxides and Oxoacids 2156.7 Sulfur Oxochlorides 2196.8 Ozone 2226.9 Swern and Related Oxidations 2266.10 Sulfur Ylides and Sulfur-Stabilized Carbanions 2286.11∗ Hydrolysis of S2F2: A Mechanistic Puzzle 2316.12 Higher-Valent Sulfur Fluorides 2346.13 Martin Sulfurane 2366.14 Lawesson’s Reagent 2386.15 Sulfur Nitrides 2406.16∗ Selenium-Mediated Oxidations 2436.17 Higher-Valent Tellurium: A Mechanistic Puzzle 2476.18 Summary 250Further Reading 2517. The Halogens 2527.1 Some Notes on Elemental Halogens 2547.2 Alkali-Induced Disproportionation of Molecular Halogens 2587.3 Acid-Induced Comproportionation of Halate and Halide 2607.4 Hypofluorous Acid, HOF 2617.5 Electrophilic Fluorinating Agents: N-Fluoro Compounds 2647.6 Oxoacids and Oxoanions 2687.7 Heptavalent Chlorine 2717.8 Interhalogen Compounds 2757.9∗ Halogens in Organic Synthesis: Some Classical Reactions 2767.10 An Introduction to Higher-Valent Organoiodine Compounds 2837.11 λ3-Iodanes 2847.12 λ5-Iodanes: IBX and Dess–Martin Periodinane 2887.13 Periodic Acid Oxidations 2907.14 Bromine Trifluoride 2917.15∗ Aryl-λ3-Bromanes 2947.16 Summary 298Further Reading 2998. The Noble Gases 3008.1 The Xenon Fluorides: Fluoride Donors and Acceptors 3028.2 O/F Ligand Exchanges 3038.3 Xenon Fluorides as F+ Donors and Oxidants 3048.4 Hydrolysis of XeF2 and XeF4 3068.5 Xenate and Perxenate 3078.6 Disproportionation of Xenate 3088.7 Hydrolysis of XeF4 3108.8 Other Compounds Containing Xe–O Bonds 3118.9 Xe–N Bonds 3128.10 Xe–C Bonds 3138.11 Krypton Difluoride 3148.12 Plus Ultra 3168.13 Summary 316Further Reading 316Epilogue 318Appendix A. Inorganic Chemistry Textbooks, with a Descriptive-Inorganic Focus 319A.1 Introductory Texts 319A.2 Advanced Texts 319Appendix B. A Short List of Advanced Organic Chemistry Textbooks 320Index 321

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