Organic chemistry / [electronic resource] T.W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder.

Includes index.

1 The Basics Bonding and Molecular Structure 1 1.1 Life and the Chemistry of Carbon Compounds-We Are Stardust 2 The Chemistry of... Natural Products 3 1.2 Atomic Structure 3 1.3 Chemical Bonds: The Octet Rule 5 1.4 How To Write Lewis Structures 7 1.5 Formal Charges and How To Calculate Them 12 1.6 Isomers: Different Compounds that Have the Same Molecular Formula 14 1.7 How To Write and Interpret Structural Formulas 15 1.8 Resonance Theory 22 1.9 Quantum Mechanics and Atomic Structure 27 1.10 Atomic Orbitals and Electron Configuration 28 1.11 Molecular Orbitals 30 1.12 The Structure of Methane and Ethane: sp3 Hybridization 32 The Chemistry of... Calculated Molecular Models: Electron Density Surfaces 36 1.13 The Structure of Ethene (Ethylene): sp 2 Hybridization 36 1.14 The Structure of Ethyne (Acetylene): sp Hybridization 40 1.15 A Summary of Important Concepts that Come from Quantum Mechanics 43 1.16 How To Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model 44 1.17 Applications of Basic Principles 47 2 Families of Carbon Compounds Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy 55 2.1 Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds 56 2.2 Polar Covalent Bonds 59 2.3 Polar and Nonpolar Molecules 61 2.4 Functional Groups 64 2.5 Alkyl Halides or Haloalkanes 65 2.6 Alcohols and Phenols 67 2.7 Ethers 69 The Chemistry of... Ethers as General Anesthetics 69 2.8 Amines 70 2.9 Aldehydes and Ketones 71 2.10 Carboxylic Acids, Esters, and Amides 73 2.11 Nitriles 75 2.12 Summary of Important Families of Organic Compounds 76 2.13 Physical Properties and Molecular Structure 77 The Chemistry of... Fluorocarbons and Teflon 81 2.14 Summary of Attractive Electric Forces 85 The Chemistry of... Organic Templates Engineered to Mimic Bone Growth 86 2.15 Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups 86 2.16 Interpreting IR Spectra 90 2.17 Applications of Basic Principles 97 3 Acids and Bases An Introduction to Organic Reactions and Their Mechanisms 104 3.1 Acid-Base Reactions 105 3.2 How To Use Curved Arrows in Illustrating Reactions 107 3.3 Lewis Acids and Bases 109 3.4 Heterolysis of Bonds to Carbon: Carbocations and Carbanions 111 3.5 The Strength of Brønsted-Lowry Acids and Bases: Ka and pKa 113 3.6 How To Predict the Outcome of Acid-Base Reactions 118 3.7 Relationships between Structure and Acidity 120 3.8 Energy Changes 123 3.9 The Relationship between the Equilibrium Constant and the Standard Free-Energy Change, ΔG ° 125 3.10 Acidity: Carboxylic Acids versus Alcohols 126 3.11 The Effect of the Solvent on Acidity 132 3.12 Organic Compounds as Bases 132 3.13 A Mechanism for an Organic Reaction 134 3.14 Acids and Bases in Nonaqueous Solutions 135 3.15 Acid-Base Reactions and the Synthesis of Deuterium- and Tritium-Labeled Compounds 136 3.16 Applications of Basic Principles 137 4 Nomenclature and Conformations of Alkanes and Cycloalkanes 4.1 Introduction to Alkanes and Cycloalkanes 145 The Chemistry of... Petroleum Refining 145 4.2 Shapes of Alkanes 146 4.3 How To Name Alkanes, Alkyl Halides, and Alcohols: The IUPAC System 148 4.4 How to Name Cycloalkanes 155 4.5 How To Name Alkenes and Cycloalkenes 158 4.6 How To Name Alkynes 160 4.7 Physical Properties of Alkanes and Cycloalkanes 161 The Chemistry of... Pheromones: Communication by Means of Chemicals 163 4.8 Sigma Bonds and Bond Rotation 164 4.9 Conformational Analysis of Butane 166 The Chemistry of... Muscle Action 168 4.10 The Relative Stabilities of Cycloalkanes: Ring Strain 168 4.11 Conformations of Cyclohexane: The Chair and the Boat 170 The Chemistry of... Nanoscale Motors and Molecular Switches 172 4.12 Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups 173 4.13 Disubstituted Cycloalkanes: Cis-Trans Isomerism 177 4.14 Bicyclic and Polycyclic Alkanes 181 4.15 Chemical Reactions of Alkanes 182 4.16 Synthesis of Alkanes and Cycloalkanes 182 4.17 How To Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency 184 4.18 Applications of Basic Principles 186 5 Stereochemistry Chiral Molecules 193 5.1 Chirality and Stereochemistry 194 5.2 Isomerism: Constitutional Isomers and Stereoisomers 195 5.3 Enantiomers and Chiral Molecules 197 5.4 Molecules Having One Chirality Center are Chiral 198 5.5 More about the Biological Importance of Chirality 201 5.6 How To Test for Chirality: Planes of Symmetry 203 5.7 Naming Enantiomers: The R,S-System 204 5.8 Properties of Enantiomers: Optical Activity 208 5.9 Racemic Forms 213 5.10 The Synthesis of Chiral Molecules 214 5.11 Chiral Drugs 216 The Chemistry of... Selective Binding of Drug Enantiomers to Left- and Right-Handed Coiled DNA 218 5.12 Molecules with More than One Chirality Center 218 5.13 Fischer Projection Formulas 224 5.14 Stereoisomerism of Cyclic Compounds 226 5.15 Relating Configurations through Reactions in Which No Bonds to the Chirality Center Are Broken 228 5.16 Separation of Enantiomers: Resolution 232 5.17 Compounds with Chirality Centers Other than Carbon 233 5.18 Chiral Molecules that Do Not Possess a Chirality Center 233 6 Nucleophilic Reactions Properties and Substitution Reactions of Alkyl Halides 240 6.1 Alkyl Halides 241 6.2 Nucleophilic Substitution Reactions 242 6.3 Nucleophiles 244 6.4 Leaving Groups 246 6.5 Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction 246 6.6 A Mechanism for the SN2 Reaction 247 6.7 Transition State Theory: Free-Energy Diagrams 249 6.8 The Stereochemistry of SN2 Reactions 252 6.9 The Reaction of tert-Butyl Chloride with Water: An SN1 Reaction 254 6.10 A Mechanism for the SN1 Reaction 255 6.11 Carbocations 257 6.12 The Stereochemistry of SN1 Reactions 259 6.13 Factors Affecting the Rates of SN1 and SN2 Reactions 262 6.14 Organic Synthesis: Functional Group Transformations Using SN2 Reactions 272 The Chemistry of... Biological Methylation: A Biological Nucleophilic Substitution Reaction 273 7 Alkenes and Alkynes I Properties and Synthesis. Elimination Reactions of Alkyl Halides 282 7.1 Introduction 283 7.2 The (E )-(Z ) System for Designating Alkene Diastereomers 283 7.3 Relative Stabilities of Alkenes 284 7.4 Cycloalkenes 287 7.5 Synthesis of Alkenes: Elimination Reactions 287 7.6 Dehydrohalogenation 288 7.7 The E2 Reaction 289 7.8 The E1 Reaction 297 7.9 Elimination and Substitution Reactions Compete With Each Other 299 7.10 Elimination of Alcohols: Acid-Catalyzed Dehydration 303 7.11 Carbocation Stability and the Occurrence of Molecular Rearrangements 308 7.12 The Acidity of Terminal Alkynes 312 7.13 Synthesis of Alkynes by Elimination Reactions 313 7.14 Terminal Alkynes Can Be Converted to Nucleophiles for Carbon-Carbon Bond Formation 315 7.15 Hydrogenation of Alkenes 317 The Chemistry of... Hydrogenation in the Food Industry 318 7.16 Hydrogenation: The Function of the Catalyst 319 7.17 Hydrogenation of Alkynes 320 7.18 An Introduction to Organic Synthesis 322 The Chemistry of... From the Inorganic to the Organic 324 8 Alkenes and Alkynes II Addition Reactions 337 8.1 Addition Reactions of Alkenes 338 8.2 Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov's Rule 340 8.3 Stereochemistry of the Ionic Addition to an Alkene 345 8.4 Addition of Water to Alkenes: Acid-Catalyzed Hydration 346 8.5 Alcohols from Alkenes through Oxymercuration-Demercuration: Markovnikov Addition 349 8.6 Alcohols from Alkenes through Hydroboration-Oxidation: Anti-Markovnikov Syn Hydration 352 8.7 Hydroboration: Synthesis of Alkylboranes 353 8.8 Oxidation and Hydrolysis of Alkylboranes 355 8.9 Summary of Alkene Hydration Methods 358 8.10 Protonolysis of Alkylboranes 359 8.11 Electrophilic Addition of Bromine and Chlorine to Alkenes 359 The Chemistry of... The Sea: A Treasury of Biologically Active Natural Products 362 8.12 Stereospecific Reactions 363 8.13 Halohydrin Formation 364 The Chemistry of...

Citrus-Flavored Soft Drinks 366 8.14 Divalent Carbon Compounds: Carbenes 366 8.15 Oxidation of Alkenes: Syn 1,2-Dihydroxylation 368 The Chemistry of... Catalytic Asymmetric Dihydroxylation 370 8.16 Oxidative Cleavage of Alkenes 371 8.17 Electrophilic Addition of Bromine and Chlorine to Alkynes 374 8.18 Addition of Hydrogen Halides to Alkynes 374 8.19 Oxidative Cleavage of Alkynes 375 8.20 How to Plan a Synthesis: Some Approaches and Examples 376 9 Nuclear Magnetic Resonance and Mass Spectrometry Tools for Structure Determination 391 9.1 Introduction 392 9.2 Nuclear Magnetic Resonance (NMR) Spectroscopy 392 9.3 How To Interpret Proton NMR Spectra 398 9.4 Shielding and Deshielding of Protons: More about Chemical Shift 401 9.5 Chemical Shift Equivalent and Nonequivalent Protons 403 9.6 Spin-Spin Coupling: More about Signal Splitting and Nonequivalent or Equivalent Protons 407 9.7 Proton NMR Spectra and Rate Processes 412 9.8 Carbon-13 NMR Spectroscopy 414 9.9 Two-Dimensional (2D) NMR Techniques 420 The Chemistry of... Magnetic Resonance Imaging in Medicine 423 9.10 An Introduction to Mass Spectrometry 423 9.11 Formation of Ions: Electron Impact Ionization 424 9.12 Depicting the Molecular Ion 424 9.13 Fragmentation 425 9.14 Isotopes in Mass Spectra 432 9.15 GC/MS Analysis 435 9.16 Mass Spectrometry of Biomolecules 436 10 Radical Reactions 10.1 Introduction: How Radicals Form and How They React 449 Hydrogen Atom Abstraction 450 Th

The 12th edition of Organic Chemistry continues Solomons, Fryhle & Snyder's tradition of excellence in teaching and preparing students for success in the organic classroom and beyond. A central theme of the authors' approach to organic chemistry is to emphasize the relationship between structure and reactivity. To accomplish this, the content is organized in a way that combines the most useful features of a functional group approach with one largely based on reaction mechanisms. The authors' philosophy is to emphasize mechanisms and their common aspects as often as possible, and at the same time, use the unifying features of functional groups as the basis for most chapters. The structural aspects of the authors' approach show students what organic chemistry is. Mechanistic aspects of their approach show students how it works. And wherever an opportunity arises, the authors' show students what it does in living systems and the physical world around us.