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Book Details
Abstract
For one-term courses in Organic Chemistry.
A comprehensive, problem-solving approach for the brief Organic Chemistry course.
Modern and thorough revisions to the streamlined, Essential Organic Chemistry focus on developing students’ problem solving and analytical reasoning skills throughout organic chemistry. Organized around reaction similarities and rich with contemporary biochemical connections, Bruice’s Third Edition discourages memorization and encourages students to be mindful of the fundamental reasoning behind organic reactivity: electrophiles react with nucleophiles.
Developed to support a diverse student audience studying organic chemistry for the first and only time, Essentials fosters an understanding of the principles of organic structure and reaction mechanisms, encourages skill development through new Tutorial Spreads and and emphasizes bioorganic processes. Contemporary and rigorous, Essentials addresses the skills needed for the 2015 MCAT and serves both pre-med and biology majors.
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Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Title Page | 5 | ||
| Copyright Page | 6 | ||
| Brief Table of Contents | 7 | ||
| Contents | 8 | ||
| Preface | 19 | ||
| About the Author | 23 | ||
| Chapter 1 Remembering General Chemistry: Electronic Structure and Bonding | 29 | ||
| Natural Organic Compounds Versus Synthetic Organic Compounds | 30 | ||
| 1.1 The Structure of an Atom | 31 | ||
| 1.2 How the Electrons in an Atom Are Distributed | 32 | ||
| 1.3 Ionic and Covalent Bonds | 34 | ||
| 1.4 How the Structure of a Compound Is Represented | 40 | ||
| PROBLEM-SOLVING STRATEGY | 42 | ||
| 1.5 Atomic Orbitals | 45 | ||
| 1.6 How Atoms Form Covalent Bonds | 46 | ||
| 1.7 How Single Bonds Are Formed in Organic Compounds | 47 | ||
| 1.8 How a Double Bond Is Formed: The Bonds in Ethene | 50 | ||
| Diamond, Graphite, Graphene, and Fullerenes: Substances that Contain Only Carbon Atoms | 52 | ||
| 1.9 How a Triple Bond Is Formed: The Bonds in Ethyne | 52 | ||
| 1.10 The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion | 54 | ||
| 1.11 The Bonds in Ammonia and in the Ammonium Ion | 56 | ||
| 1.12 The Bonds in Water | 57 | ||
| Water-A Compound Central to Life | 58 | ||
| 1.13 The Bond in a Hydrogen Halide | 58 | ||
| 1.14 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles | 60 | ||
| PROBLEM-SOLVING STRATEGY | 62 | ||
| 1.15 The Dipole Moments of Molecules | 63 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 64 | ||
| PROBLEMS | 65 | ||
| Chapter 2 Acids and Bases: Central to Understanding Organic Chemistry | 68 | ||
| 2.1 An Introduction to Acids and Bases | 68 | ||
| 2.2 pKa and pH | 70 | ||
| Acid Rain | 72 | ||
| 2.3 Organic Acids and Bases | 72 | ||
| Poisonous Amines | 73 | ||
| PROBLEM-SOLVING STRATEGY | 75 | ||
| 2.4 How to Predict the Outcome of an Acid-Base Reaction | 76 | ||
| 2.5 How to Determine the Position of Equilibrium | 76 | ||
| 2.6 How the Structure of an Acid Affects Its pKa Value | 77 | ||
| 2.7 How Substituents Affect the Strength of an Acid | 81 | ||
| PROBLEM-SOLVING STRATEGY | 82 | ||
| 2.8 An Introduction to Delocalized Electrons | 83 | ||
| Fosamax Prevents Bones from Being Nibbled Away | 84 | ||
| 2.9 A Summary of the Factors that Determine Acid Strength | 85 | ||
| 2.10 How pH Affects the Structure of an Organic Compound | 86 | ||
| PROBLEM-SOLVING STRATEGY | 87 | ||
| Aspirin Must Be in Its Basic Form to Be Physiologically Active | 88 | ||
| 2.11 Buffer Solutions | 89 | ||
| Blood: A Buffered Solution | 89 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 90 | ||
| PROBLEMS | 91 | ||
| TUTORIAL Acids and Bases | 93 | ||
| Chapter 3 An Introduction to Organic Compounds | 101 | ||
| 3.1 How Alkyl Substituents Are Named | 104 | ||
| Bad-Smelling Compounds | 105 | ||
| 3.2 The Nomenclature of Alkanes | 108 | ||
| How is the Octane Number of Gasoline Determined? | 110 | ||
| 3.3 The Nomenclature of Cycloalkanes • Skeletal Structures | 111 | ||
| PROBLEM-SOLVING STRATEGY | 112 | ||
| 3.4 The Nomenclature of Alkyl Halides | 114 | ||
| PROBLEM-SOLVING STRATEGY | 114 | ||
| 3.5 The Classification of Alkyl Halides, Alcohols, and Amines | 115 | ||
| Nitrosamines and Cancer | 115 | ||
| 3.6 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines | 116 | ||
| 3.7 Noncovalent Interactions | 118 | ||
| PROBLEM-SOLVING STRATEGY | 121 | ||
| Drugs Bind to Their Receptors | 122 | ||
| 3.8 Factors that Affect the Solubility of Organic Compounds | 122 | ||
| Cell Membranes | 125 | ||
| 3.9 Rotation Occurs About Carbon-Carbon Single Bonds | 125 | ||
| 3.10 Some Cycloalkanes have Angle Strain | 128 | ||
| Von Baeyer, Barbituric Acid, and Blue Jeans | 129 | ||
| 3.11 Conformers of Cyclohexane | 129 | ||
| 3.12 Conformers of Monosubstituted Cyclohexanes | 132 | ||
| Starch and Cellulose-Axial and Equatorial | 133 | ||
| 3.13 Conformers of Disubstituted Cyclohexanes | 134 | ||
| PROBLEM-SOLVING STRATEGY | 134 | ||
| 3.14 Fused Cyclohexane Rings | 137 | ||
| Cholesterol and Heart Disease | 138 | ||
| How High Cholesterol Is Treated Clinically | 138 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 139 | ||
| PROBLEMS | 139 | ||
| Chapter 4 Isomers: The Arrangement of Atoms in Space | 144 | ||
| 4.1 CIS-Trans Isomers Result from Restricted Rotation | 145 | ||
| Cis-Trans Interconversion in Vision | 148 | ||
| 4.2 Designating Geometric Isomers Using the E,Z System | 148 | ||
| PROBLEM-SOLVING STRATEGY | 151 | ||
| 4.3 A Chiral Object Has a Nonsuperimposable Mirror Image | 151 | ||
| 4.4 An Asymmetric Center Is a Cause of Chirality in a Molecule | 152 | ||
| 4.5 Isomers with One Asymmetric Center | 153 | ||
| 4.6 How to Draw Enantiomers | 154 | ||
| 4.7 Naming Enantiomers by the R,S System | 154 | ||
| PROBLEM-SOLVING STRATEGY | 156 | ||
| PROBLEM-SOLVING STRATEGY | 157 | ||
| 4.8 Chiral Compounds Are Optically Active | 158 | ||
| 4.9 How Specific Rotation Is Measured | 160 | ||
| 4.10 Isomers with More than One Asymmetric Center | 162 | ||
| 4.11 Stereoisomers of Cyclic Compounds | 163 | ||
| PROBLEM-SOLVING STRATEGY | 164 | ||
| 4.12 Meso Compounds Have Asymmetric Centers but Are Optically Inactive | 165 | ||
| PROBLEM-SOLVING STRATEGY | 167 | ||
| 4.13 Receptors | 168 | ||
| The Enantiomers of Thalidomide | 170 | ||
| 4.14 How Enantiomers Can Be Separated | 170 | ||
| Chiral Drugs | 171 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 171 | ||
| PROBLEMS | 172 | ||
| Chapter 5 Alkenes | 176 | ||
| Pheromones | 177 | ||
| 5.1 The Nomenclature of Alkenes | 177 | ||
| 5.2 How an Organic Compound Reacts Depends on its Functional Group | 180 | ||
| 5.3 How Alkenes React . Curved Arrows Show the Flow of Electrons | 181 | ||
| A Few Words About Curved Arrows | 183 | ||
| 5.4 Thermodynamics: How Much Product Is Formed? | 185 | ||
| 5.5 Increasing the Amount of Product Formed in a Reaction | 187 | ||
| 5.6 Using ΔH° Values to Determine the Relative Stabilities of Alkenes | 188 | ||
| PROBLEM-SOLVING STRATEGY | 189 | ||
| Trans Fats | 192 | ||
| 5.7 Kinetics: How Fast Is the Product Formed? | 192 | ||
| 5.8 The Rate of a Chemical Reaction | 194 | ||
| 5.9 The Reaction Coordinate Diagram for the Reaction of 2-Butene with HBr | 194 | ||
| 5.10 Catalysis | 196 | ||
| 5.11 Catalysis by Enzymes | 197 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 199 | ||
| PROBLEMS | 200 | ||
| TUTORIAL An Exercise in Drawing Curved Arrows: Pushing Electrons | 202 | ||
| Chapter 6 The Reactions of Alkenes and Alkynes | 210 | ||
| Green Chemistry: Aiming for Sustainability | 211 | ||
| 6.1 The Addition of a Hydrogen Halide to an Alkene | 211 | ||
| 6.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon | 212 | ||
| 6.3 Electrophilic Addition Reactions Are Regioselective | 215 | ||
| Which Are More Harmful, Natural Pesticides or Synthetic Pesticides? | 217 | ||
| PROBLEM-SOLVING STRATEGY | 217 | ||
| 6.4 A Carbocation will Rearrange if It Can Form a More Stable Carbocation | 219 | ||
| 6.5 The Addition of Water to an Alkene | 221 | ||
| 6.6 The Stereochemistry of Alkene Reactions | 222 | ||
| PROBLEM-SOLVING STRATEGY | 224 | ||
| 6.7 The Stereochemistry of Enzyme-Catalyzed Reactions | 225 | ||
| 6.8 Enantiomers Can Be Distinguished by Biological Molecules | 226 | ||
| 6.9 An Introduction to Alkynes | 227 | ||
| Synthetic Alkynes Are Used to Treat Parkinson's Disease | 228 | ||
| Why Are Drugs So Expensive? | 229 | ||
| 6.10 The Nomenclature of Alkynes | 229 | ||
| Synthetic Alkynes Are Used for Birth Control | 230 | ||
| 6.11 The Structure of Alkynes | 231 | ||
| 6.12 The Physical Properties of Unsaturated Hydrocarbons | 231 | ||
| 6.13 The Addition of a Hydrogen Halide to an Alkyne | 232 | ||
| 6.14 The Addition of Water to an Alkyne | 233 | ||
| 6.15 The Addition of Hydrogen to an Alkyne | 235 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 236 | ||
| SUMMARY OF REACTIONS | 237 | ||
| PROBLEMS | 238 | ||
| Chapter 7 Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and the Reactions of Benzene | 242 | ||
| 7.1 Delocalized Electrons Explain Benzene's Structure | 243 | ||
| Kekule's Dream | 245 | ||
| 7.2 The Bonding in Benzene | 245 | ||
| 7.3 Resonance Contributors and the Resonance Hybrid | 246 | ||
| 7.4 How to Draw Resonance Contributors | 247 | ||
| Electron Delocalization Affects the Three-Dimensional Shape of Proteins | 250 | ||
| 7.5 The Predicted Stabilities of Resonance Contributors | 250 | ||
| 7.6 Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound | 252 | ||
| 7.7 Delocalized Electrons Increase Stability | 253 | ||
| PROBLEM-SOLVING STRATEGY | 255 | ||
| PROBLEM-SOLVING STRATEGY | 256 | ||
| 7.8 Delocalized Electrons Affect pKa Values | 256 | ||
| PROBLEM-SOLVING STRATEGY | 259 | ||
| 7.9 Electronic Effects | 259 | ||
| 7.10 Delocalized Electrons Can Affect the Product of a Reaction | 262 | ||
| 7.11 Reactions of Dienes | 263 | ||
| 7.12 The Diels-Alder Reaction Is a 1, 4-Addition Reaction | 266 | ||
| 7.13 Benzene Is an Aromatic Compound | 268 | ||
| 7.14 The Two Criteria for Aromaticity | 269 | ||
| 7.15 Applying the Criteria for Aromaticity | 270 | ||
| Buckyballs | 271 | ||
| 7.16 How Benzene Reacts | 272 | ||
| 7.17 The Mechanism for Electrophilic Aromatic Substitution Reactions | 273 | ||
| Thyroxine | 275 | ||
| 7.18 Organizing What We Know About the Reactions of Organic Compounds | 276 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 277 | ||
| SUMMARY OF REACTIONS | 277 | ||
| PROBLEMS | 278 | ||
| TUTORIAL: DRAWING RESONANCE CONTRIBUTORS | 283 | ||
| Chapter 8 Substitution and Elimination Reactions of Alkyl Halides | 291 | ||
| DDT: A Synthetic Organohalide That Kills Disease-Spreading Insects | 292 | ||
| 8.1 The Mechanism for an SN2 Reaction | 293 | ||
| 8.2 Factors That Affect SN2 Reactions | 297 | ||
| Why Are Living Organisms Composed of Carbon Instead of Silicon? | 301 | ||
| 8.3 The Mechanism for an SN1 Reaction | 301 | ||
| 8.4 Factors That Affect SN1 Reactions | 304 | ||
| 8.5 Comparing SN2 and SN1 Reactions | 305 | ||
| PROBLEM-SOLVING STRATEGY | 305 | ||
| Naturally Occurring Organohalides That Defend against Predators | 307 | ||
| 8.6 Intermolecular versus Intramolecular Reactions | 307 | ||
| PROBLEM-SOLVING STRATEGY | 309 | ||
| 8.7 Elimination Reactions of Alkyl Halides | 309 | ||
| 8.8 The Products of an Elimination Reaction | 311 | ||
| 8.9 Relative Reactivities of Alkyl Halides Reactions | 315 | ||
| The Nobel Prize | 316 | ||
| 8.10 Does a Tertiary Alkyl Halide Undergo SN2/E2 Reactions or SN1/E1 Reactions? | 316 | ||
| 8.11 Competition between Substitution and Elimination | 317 | ||
| 8.12 Solvent Effects | 320 | ||
| Solvation Efects | 320 | ||
| 8.13 Substitution Reactions in Synthesis | 324 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 325 | ||
| SUMMARY OF REACTIONS | 326 | ||
| PROBLEMS | 327 | ||
| Chapter 9 Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols | 331 | ||
| 9.1 The Nomenclature of Alcohols | 331 | ||
| Grain Alcohol and Wood Alcohol | 333 | ||
| 9.2 Activating an Alcohol for Nucleophilic Substitution by Protonation | 334 | ||
| 9.3 Activating an OH Group for Nucleophilic Substitution in a Cell | 336 | ||
| The Inability to Perform an SN2 Reaction Causes a Severe Clinical Disorder | 338 | ||
| 9.4 Elimination Reactions of Alcohols: Dehydration | 338 | ||
| 9.5 Oxidation of Alcohols | 341 | ||
| Blood Alcohol Content | 343 | ||
| Treating Alcoholism with Antabuse | 343 | ||
| Methanol Poisoning | 344 | ||
| 9.6 Nomenclature of Ethers | 344 | ||
| 9.7 Nucleophilic Substitution Reactions of Ethers | 345 | ||
| Anesthetics | 347 | ||
| 9.8 Nucleophilic Substitution Reactions of Epoxides | 347 | ||
| 9.9 Using Carbocation Stability to Determine the Carcinogenicity of an Arene Oxide | 351 | ||
| Benzo[a]pyrene and Cancer | 353 | ||
| Chimney Sweeps and Cancer | 354 | ||
| 9.10 Amines Do Not Undergo Substitution or Elimination Reactions | 354 | ||
| Alkaloids | 355 | ||
| Lead Compounds for the Development of Drugs | 356 | ||
| 9.11 Thiols, Sulfides, and Sulfonium Salts | 356 | ||
| Mustard Gas-A Chemical Warfare Agent | 357 | ||
| Alkylating Agents as Cancer Drugs | 358 | ||
| 9.12 Methylating Agents Used by Chemists versus Those Used by Cells | 358 | ||
| Eradicating Termites | 359 | ||
| S-Adenosylmethionine: A Natural Antidepressant | 360 | ||
| 9.13 Organizing What We Know about the Reactions of Organic Compounds | 360 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 361 | ||
| SUMMARY OF REACTIONS | 361 | ||
| PROBLEMS | 363 | ||
| Chapter 10 Determining the Structure of Organic Compounds | 367 | ||
| 10.1 Mass Spectrometry | 368 | ||
| 10.2 The Mass Spectrum • Fragmentation | 369 | ||
| 10.3 Using The m/z Value of The Molecular Ion to Calculate the Molecular Formula | 371 | ||
| PROBLEM-SOLVING STRATEGY | 372 | ||
| 10.4 Isotopes in Mass Spectrometry | 373 | ||
| 10.5 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas | 374 | ||
| 10.6 Fragmentation Patterns | 375 | ||
| 10.7 Gas Chromatography-Mass Spectrometry | 376 | ||
| Mass Spectrometry in Forensics | 376 | ||
| 10.8 Spectroscopy and the Electromagnetic Spectrum | 376 | ||
| 10.9 Infrared Spectroscopy | 378 | ||
| 10.10 Characteristic Infrared Absorption Bands | 379 | ||
| 10.11 The Intensity of Absorption Bands | 379 | ||
| 10.12 The Position of Absorption Bands | 380 | ||
| 10.13 The Position and Shape of an Absorption Band Is Affected by Electron Delocalization,\r Electron\r Donation and Withdrawal, and Hydrogen Bonding | 380 | ||
| PROBLEM-SOLVING STRATEGY | 382 | ||
| 10.14 The Absence of Absorption Bands | 385 | ||
| 10.15 How to Interpret an Infrared Spectrum | 386 | ||
| 10.16 Ultraviolet and Visible Spectroscopy | 387 | ||
| Ultraviolet Light and Sunscreens | 388 | ||
| 10.17 The Effect of Conjugation on Amax | 389 | ||
| 10.18 The Visible Spectrum and Color | 390 | ||
| What Makes Blueberries Blue and Strawberries Red? | 391 | ||
| 10.19 Some Uses of UV/VIS Spectroscopy | 391 | ||
| 10.20 An Introduction to NMR Spectroscopy | 392 | ||
| Nikola Tesla (1856-1943) | 393 | ||
| 10.21 Shielding Causes Different Hydrogens to Show Signals at Different Frequencies | 394 | ||
| 10.22 The Number of Signals in an 1H NMR Spectrum | 395 | ||
| 10.23 The Chemical Shift Tells How Far the Signal Is from the Reference Signal | 396 | ||
| 10.24 The Relative Positions of 1H NMR Signals | 397 | ||
| 10.25 The Characteristic Values of Chemical Shifts | 397 | ||
| 10.26 The Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal | 399 | ||
| 10.27 The Splitting of Signals Is Described by the N + 1 Rule | 401 | ||
| 10.28 More Examples of 1H NMR Spectra | 404 | ||
| PROBLEM-SOLVING STRATEGY | 406 | ||
| 10.29 13C NMR Spectroscopy | 407 | ||
| PROBLEM-SOLVING STRATEGY | 410 | ||
| NMR Used in Medicine is Called Magnetic Resonance Imaging | 411 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 412 | ||
| PROBLEMS | 413 | ||
| Chapter 11 Reactions of Carboxylic Acids and Carboxylic Acid Derivatives | 421 | ||
| 11.1 The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives | 423 | ||
| Nature's Sleeping Pill | 425 | ||
| 11.2 The Structures of Carboxylic Acids and Carboxylic Acid Derivatives | 426 | ||
| 11.3 The Physical Properties of Carbonyl Compounds | 427 | ||
| 11.4 How Carboxylic Acids and Carboxylic Acid Derivatives React | 427 | ||
| PROBLEM-SOLVING STRATEGY | 429 | ||
| 11.5 The Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives | 430 | ||
| 11.6 The Reactions of Acyl Chlorides | 431 | ||
| 11.7 The Reactions of Esters | 432 | ||
| 11.8 Acid-Catalyzed Ester Hydrolysis and Transesterification | 434 | ||
| 11.9 Hydroxide-Ion-Promoted Ester Hydrolysis | 437 | ||
| Aspirin, NSAID s, and COX-2 Inhibitors | 438 | ||
| 11.10 Reactions of Carboxylic Acids | 440 | ||
| 11.11 Reactions of Amides | 441 | ||
| Dalmatians: Do Not Fool with Mother Nature | 442 | ||
| 11.12 Acid-Catalyzed Amide Hydrolysis and Alcoholysis | 442 | ||
| The Discovery of Penicillin | 444 | ||
| Penicillin and Drug Resistance | 444 | ||
| Penicillins in Clinical Use | 445 | ||
| A Semisynthetic Penicillin | 445 | ||
| 11.13 Nitriles | 446 | ||
| 11.14 Acid Anhydrides | 447 | ||
| What Drug-Enforcement Dogs Are Really Detecting | 449 | ||
| 11.15 How Chemists Activate Carboxylic Acids | 449 | ||
| 11.16 How Cells Activate Carboxylic Acids | 450 | ||
| Nerve Impulses, Paralysis, and Insecticides | 453 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 454 | ||
| SUMMARY OF REACTIONS | 454 | ||
| PROBLEMS | 456 | ||
| Chapter 12 Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives | 459 | ||
| 12.1 The Nomenclature of Aldehydes and Ketones | 460 | ||
| Butanedione: An Unpleasant Compound | 461 | ||
| 12.2 The Relative Reactivities of Carbonyl Compounds | 462 | ||
| 12.3 How Aldehydes and Ketones React | 463 | ||
| 12.4 Organometallic Compounds | 463 | ||
| 12.5 The Reactions of Carbonyl Compounds with Grignard Reagents | 465 | ||
| Synthesizing Organic Compounds | 467 | ||
| Semisynthetic Drugs | 468 | ||
| PROBLEM-SOLVING STRATEGY | 469 | ||
| 12.6 The Reactions of Aldehydes and Ketones with Cyanide Ion | 469 | ||
| 12.7 The Reactions of Carbonyl Compounds with Hydride Ion | 470 | ||
| 12.8 The Reactions of Aldehydes and Ketones with Amines | 473 | ||
| Serendipity in Drug Development | 476 | ||
| 12.9 The Reactions of Aldehydes and Ketones with Alcohols | 477 | ||
| Carbohydrates Form Hemiacetals and Acetals | 479 | ||
| 12.10 Nucleophilic Addition to a,B-Unsaturated Aldehydes and Ketones | 479 | ||
| 12.11 Nucleophilic Addition to a,B-Unsaturated Carboxylic Acid Derivatives | 481 | ||
| Enzyme-Catalyzed Cis-Trans Interconversion | 481 | ||
| 12.12 Conjugate Addition Reactions in Biological Systems | 482 | ||
| Cancer Chemotherapy | 482 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 483 | ||
| SUMMARY OF REACTIONS | 483 | ||
| PROBLEMS | 485 | ||
| Chapter 13 Reactions at the a-Carbon of Carbonyl Compounds | 489 | ||
| 13.1 The Acidity of an a-Hydrogen | 490 | ||
| PROBLEM-SOLVING STRATEGY | 492 | ||
| 13.2 Keto-Enol Tautomers | 492 | ||
| 13.3 Keto-Enol Interconversion | 493 | ||
| 13.4 Alkylation of Enolate Ions | 495 | ||
| The Synthesis of Aspirin | 496 | ||
| 13.5 An Aldol Addition Forms B-Hydroxyaldehydes or B-Hydroxyketones | 496 | ||
| 13.6 The Dehydration of Aldol Addition Products forms a,B-Unsaturated Aldehydes and Ketones | 498 | ||
| 13.7 A Crossed Aldol Addition | 499 | ||
| Breast Cancer and Aromatase Inhibitors | 500 | ||
| 13.8 A Claisen Condensation Forms a B-Keto Ester | 500 | ||
| 13.9 CO2 Can Be Removed from a Carboxylic Acid with a Carbonyl Group at the 3-Position | 503 | ||
| 13.10 Reactions at the a-Carbon in Cells | 504 | ||
| 13.11 Organizing What We Know about the Reactions of Organic Compounds | 508 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 508 | ||
| SUMMARY OF REACTIONS | 509 | ||
| PROBLEMS | 510 | ||
| Chapter 14 Radicals | 513 | ||
| 14.1 Alkanes are Unreactive Compounds | 513 | ||
| Natural Gas and Petroleum | 514 | ||
| Fossil Fuels: A Problematic Energy Source | 514 | ||
| 14.2 The Chlorination and Bromination of Alkanes | 515 | ||
| Why Radicals No Longer Have to Be Called Free Radicals | 516 | ||
| 14.3 Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron | 516 | ||
| 14.4 The Distribution of Products Depends on Radical Stability | 517 | ||
| PROBLEM-SOLVING STRATEGY | 518 | ||
| 14.5 The Stereochemistry of Radical Substitution Reactions | 519 | ||
| 14.6 Formation of Explosive Peroxides | 520 | ||
| 14.7 Radical Reactions Occur in Biological Systems | 521 | ||
| Decaffeinated Coffee and the Cancer Scare | 522 | ||
| Food Preservatives | 523 | ||
| Is Chocolate a Health Food? | 523 | ||
| 14.8 Radicals and Stratospheric Ozone | 524 | ||
| Artificial Blood | 525 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 525 | ||
| SUMMARY OF REACTIONS | 525 | ||
| PROBLEMS | 526 | ||
| Chapter 15 Synthetic Polymers | 527 | ||
| 15.1 There Are Two Major Classes of Synthetic Polymers | 528 | ||
| 15.2 Chain-Growth Polymers | 529 | ||
| Teflon: An Accidental Discovery | 532 | ||
| Recycling Symbols | 533 | ||
| 15.3 Stereochemistry of Polymerization • Ziegler-Natta Catalysts | 538 | ||
| 15.4 Organic Compounds That Conduct Electricity | 539 | ||
| 15.5 Polymerization of Dienes • Natural and Synthetic Rubber | 540 | ||
| 15.6 Copolymers | 542 | ||
| Nanocontainers | 542 | ||
| 15.7 Step-Growth Polymers | 543 | ||
| 15.8 Classes of Step-Growth Polymers | 543 | ||
| Health Con cerns: Bisphenol A and Phthalates | 547 | ||
| Designing a Polymer | 547 | ||
| 15.9 Recycling Polymers | 549 | ||
| 15.10 Biodegradable Polymers | 549 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 550 | ||
| PROBLEMS | 551 | ||
| Chapter 16 The Organic Chemistry of Carbohydrates | 553 | ||
| 16.1 Classification of Carbohydrates | 554 | ||
| 16.2 The D and L Notations | 555 | ||
| 16.3 The Configurations of Aldoses | 556 | ||
| 16.4 The Configurations of Ketoses | 557 | ||
| 16.5 The Reactions of Monosaccharides in Basic Solutions | 558 | ||
| Measuring the Blood Glucose Levels in Diabetes | 559 | ||
| 16.6 Monosaccharides Form Cyclic Hemiacetals | 560 | ||
| Vitamin C | 562 | ||
| 16.7 Glucose Is the Most Stable Aldohexose | 563 | ||
| 16.8 Formation of Glycosides | 564 | ||
| 16.9 Disaccharides | 566 | ||
| Lactose Intolerance | 567 | ||
| 16.10 Polysaccharides | 568 | ||
| Why the Dentist Is Right | 569 | ||
| Heparin-A Natural Anticoagulant | 569 | ||
| Controlling Fleas | 571 | ||
| 16.11 Carbohydrates on Cell Surfaces | 571 | ||
| 16.12 Artificial Sweeteners | 572 | ||
| Acceptable Daily Intake | 574 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 574 | ||
| SUMMARY OF REACTIONS | 575 | ||
| PROBLEMS | 575 | ||
| Chapter 17 The Organic Chemistry of Amino Acids, Peptides, and Proteins | 577 | ||
| 17.1 The Nomenclature of Amino Acids | 578 | ||
| Proteins and Nutrition | 581 | ||
| 17.2 The Configuration of Amino Acids | 582 | ||
| Amino Acids and Disease | 582 | ||
| 17.3 The Acid-Base Properties of Amino Acids | 583 | ||
| 17.4 The Isoelectric Point | 584 | ||
| 17.5 Separating Amino Acids | 585 | ||
| Water Softeners: Examples of Cation-Exchange Chromatography | 588 | ||
| 17.6 The Synthesis of Amino Acids | 589 | ||
| 17.7 The Resolution of Racemic Mixtures of Amino Acids | 590 | ||
| 17.8 Peptide Bonds and Disulfide Bonds | 591 | ||
| Runner's High | 592 | ||
| Diabetes | 594 | ||
| Hair: Straight or Curly? | 594 | ||
| 17.9 An Introduction to Protein Structure | 595 | ||
| Primary Structure and Taxonomic Relationship | 595 | ||
| 17.10 How to Determine the Primary Structure of a Polypeptide or a Protein | 595 | ||
| PROBLEM-SOLVING STRATEGY | 597 | ||
| 17.11 Secondary Structure | 600 | ||
| 17.12 Tertiary Structure | 602 | ||
| Diseases Caused by a Misfolded Protein | 603 | ||
| 17.13 Quaternary Structure | 604 | ||
| 17.14 Protein Denaturation | 605 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 605 | ||
| PROBLEMS | 606 | ||
| Chapter 18 How Enzymes Catalyze Reactionss . The Organic Chemistry of the Vitamins available on-line | Online-1 | ||
| 18.1 Enzyme-Catalyzed Reactions | Online-1 | ||
| 18.2 An Enzyme-Catalyzed Reaction That Involves Two Sequential SN2 Reactions | Online-4 | ||
| How Tamiflu Works | Online-5 | ||
| 18.3 An Enzyme-Catalyzed Reaction That Is Reminiscent of Acid-Catalyzed Amide and Ester Hydrolysis | Online-8 | ||
| 18.4 An Enzyme-Catalyzed Reaction That Is Reminiscent of the Base-Catalyzed Enediol Rearrangement | Online-10 | ||
| 18.5 An Enzyme-Catalyzed Reaction That Is Reminiscent of a Retro-Aldol Addition | Online-12 | ||
| 18.6 Vitamins and Coenzymes | Online-13 | ||
| Vitamin B1 | Online-15 | ||
| 18.7 Niacin: The Vitamin Needed for Many Redox Reactions | Online-15 | ||
| Niacin Deficiency | Online-16 | ||
| 18.8 Riboflavin: Another Vitamin Used in Redox Reactions | Online-20 | ||
| 18.9 Vitamin B1: The Vitamin Needed for Acyl Group Transfer | Online-23 | ||
| Curing a Hangover with Vitamin B1 | Online-26 | ||
| 18.10 Vitamin H: The Vitamin Needed for Carboxylation of an a-Carbon | Online-28 | ||
| PROBLEM-SOLVING STRATEGY | Online-30 | ||
| 18.11 Vitamin B6: The Vitamin Needed for Amino Acid Transformations | Online-30 | ||
| Assessing the Damage After a Heart Attack | Online-34 | ||
| 18.12 Vitamin B12: The Vitamin Needed for Certain Isomerizations | Online-35 | ||
| 18.13 Folic Acid: The Vitamin Needed for One-Carbon Transfer | Online-37 | ||
| The First Antibiotics | Online-38 | ||
| Competitive Inhibitors | Online-41 | ||
| Cancer Drugs and Side Efects | Online-41 | ||
| 18.14 Vitamin K: The Vitamin Needed for Carboxylation of Glutamate | Online-41 | ||
| Anticoagulants | Online-42 | ||
| Too Much Broccoli | Online-43 | ||
| SOME IMPORTANT THINGS TO REMEMBER | Online-43 | ||
| PROBLEMS | Online-44 | ||
| Chapter 19 The Organic Chemistry of the Metabolic Pathways | 609 | ||
| Differences in Metabolism | 610 | ||
| 19.1 ATP Is Used for Phosphoryl Transfer Reactions | 610 | ||
| Why Did Nature Choose Phosphates? | 611 | ||
| 19.2 The \"High-Energy\" Character of Phosphoanhydride Bonds | 611 | ||
| 19.3 The Four Stages of Catabolism | 612 | ||
| 19.4 The Catabolism of Fats | 613 | ||
| 19.5 The Catabolism of Carbohydrates | 616 | ||
| PROBLEM-SOLVING STRATEGY | 620 | ||
| 19.6 The Fate of Pyruvate | 620 | ||
| 19.7 The Catabolism of Proteins | 621 | ||
| Phenylketonuria (PKU): An Inborn Error of Metabolism | 623 | ||
| 19.8 The Citric Acid Cycle | 623 | ||
| 19.9 Oxidative Phosphorylation | 626 | ||
| Basal Metabolic Rate | 627 | ||
| 19.10 Anabolism | 627 | ||
| 19.11 Gluconeogenesis | 628 | ||
| 19.12 Regulating Metabolic Pathways | 629 | ||
| 19.13 Amino Acid Biosynthesis | 630 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 631 | ||
| PROBLEMS | 632 | ||
| Chapter 20 The Organic Chemistry of Lipids | 634 | ||
| 20.1 Fatty Acids Are Long-Chain Carboxylic Acids | 635 | ||
| Omega Fatty Acids | 636 | ||
| Waxes Are Esters That Have High Molecular Weights | 636 | ||
| 20.2 Fats and Oils Are Triglycerides | 637 | ||
| Whales and Echolocation | 638 | ||
| 20.3 Soaps and Detergents | 638 | ||
| 20.4 Phosphoglycerides and Sphingolipids | 640 | ||
| Snake Venom | 641 | ||
| Multiple Sclerosis and the Myelin Sheath | 642 | ||
| 20.5 Prostaglandins Regulate Physiological Responses | 642 | ||
| 20.6 Terpenes Contain Carbon Atoms in Multiples of Five | 642 | ||
| 20.7 How Terpenes are Biosynthesized | 644 | ||
| PROBLEM-SOLVING STRATEGY | 645 | ||
| 20.8 How Nature Synthesizes Cholesterol | 646 | ||
| 20.9 Synthetic Steroids | 647 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 648 | ||
| PROBLEMS | 648 | ||
| Chapter 21 The Chemistry of the Nucleic Acids | 650 | ||
| 21.1 Nucleosides and Nucleotides | 650 | ||
| The Structure of DNA: Watson, Crick, Franklin, and Wilkins | 653 | ||
| 21.2 Nucleic Acids Are Composed of Nucleotide Subunits | 653 | ||
| 21.3 The Secondary Structure of DNA-The Double Helix | 654 | ||
| 21.4 Why DNA Does Not Have a 2'-OH Group | 656 | ||
| 21.5 The Biosynthesis of DNA Is Called Replication | 657 | ||
| 21.6 DNA and Heredity | 658 | ||
| Natural Products That Modify DNA | 658 | ||
| 21.7 The Biosynthesis of RNA Is Called Transcription | 659 | ||
| 21.8 The RNAs Used for Protein Biosynthesis | 660 | ||
| 21.9 The Biosynthesis of Proteins Is Called Translation | 662 | ||
| Sickle Cell Anemia | 664 | ||
| Antibiotics That Act by Inhibiting Translation | 664 | ||
| 21.10 Why DNA Contains Thymine Instead of Uracil | 665 | ||
| Antibiotics Act by a Common Mechanism | 666 | ||
| 21.11 Antiviral Drugs | 666 | ||
| Influenza Pandemics | 667 | ||
| 21.12 How the Base Sequence of DNA Is Determined | 667 | ||
| 21.13 Genetic Engineering | 669 | ||
| Resisting Herbicides | 669 | ||
| Using Genetic Engineering to Treat the Ebola Virus | 670 | ||
| SOME IMPORTANT THINGS TO REMEMBER | 670 | ||
| PROBLEMS | 671 | ||
| Appendix I Physical Properties of Organic Compounds | Online-A-1 | ||
| Appendix II Spectroscopy Tables | Online-A-8 | ||
| Answers to Selected Problems | A-1 | ||
| Glossary | G-1 | ||
| Photo Credits | P-1 | ||
| Index | I-1 | ||
| A | I-1 | ||
| B | I-2 | ||
| C | I-3 | ||
| D | I-4 | ||
| E | I-4 | ||
| F | I-5 | ||
| G | I-5 | ||
| H | I-5 | ||
| I | I-6 | ||
| J | I-6 | ||
| K | I-6 | ||
| L | I-6 | ||
| M | I-6 | ||
| N | I-7 | ||
| O | I-7 | ||
| P | I-7 | ||
| Q | I-8 | ||
| R | I-8 | ||
| S | I-9 | ||
| T | I-9 | ||
| U | I-10 | ||
| V | I-10 | ||
| W | I-10 | ||
| X | I-10 | ||
| Y | I-10 | ||
| Z | I-10 |