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Organic Chemistry, 10th Edition

December 2009, ©2011
Organic Chemistry, 10th Edition (EHEP000270) cover image
The Tenth Edition of Organic Chemistry continues Solomons/Fryhle’s tradition of excellence in teaching and preparing students for success in the organic classroom and beyond. In the Tenth Edition, virtually every aspect of the teaching and learning solution has been revisited and redesigned to assist students in comprehending the fundamentals of organic chemistry. The authors’ thoroughly explain and illustrate each new idea when it is first introduced and then reinforce the new idea or concept by having students work related problems.
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1 THE BASICS: Bonding and Molecular Structure   1

1.1 We Are Stardust  2

1.2 Atomic Structure 2

1.3 The Structural Theory of Organic Chemistry 5

1.4 Chemical Bonds: The Octet Rule 7

1.5 How to Write Lewis Structures 9

1.6 Exceptions to the Octet Rule 11

1.7 Formal Charges and How to Calculate Them 13

1.8 Resonance Theory 15

1.9 Quantum Mechanics and Atomic Structure 20

1.10 Atomic Orbitals and Electron Configuration 21

1.11 Molecular Orbitals 23

1.12 The Structure of Methane and Ethane: sp3 Hybridization 25

THE CHEMISTRY OF . . . Calculated Molecular Models: Electron Density Surfaces 29

1.13 The Structure of Ethene (Ethylene): sp2 Hybridization 30

1.14 The Structure of Ethyne (Acetylene): sp Hybridization 34

1.15 A Summary of Important Concepts that Come from Quantum Mechanics 36

1.16 Molecular Geometry: The Valence Shell Electron Pair Repulsion Model 38

1.17 How to Interpret and Write Structural Formulas 41

1.18 Applications of Basic Principles 46

2 FAMILIES OF CARBON COMPOUNDS: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy 53

2.1 Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds 54

2.2 Polar Covalent Bonds 57

THE CHEMISTRY OF . . . Calculated Molecular Models: Maps of Electrostatic Potential 59

2.3 Polar and Nonpolar Molecules 60

2.4 Functional Groups 62

2.5 Alkyl Halides or Haloalkanes 64

2.6 Alcohols 65

2.7 Ethers 67

THE CHEMISTRY OF . . . Ethers as General Anesthetics 67

2.8 Amines 68

2.9 Aldehydes and Ketones 69

2.10 Carboxylic Acids, Esters, and Amides 70

2.11 Nitriles 72

2.12 Summary of Important Families of Organic Compounds 72

2.13 Physical Properties and Molecular Structure 73

THE CHEMISTRY OF . . . Fluorocarbons and Teflon 78

2.14 Summary of Attractive Electric Forces 82

THE CHEMISTRY OF . . . Organic Templates Engineered to Mimic Bone Growth 82

2.15 Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups 83

2.16 Interpreting IR Spectra 87

2.17 Applications of Basic Principles 92

3 AN INTRODUCTION TO ORGANIC REACTIONS AND THEIR MECHANISMS: Acids and Bases 98

3.1 Reactions and Their Mechanisms 99

3.2 Acid-Base Reactions 101

3.3 Lewis Acids and Bases 102

3.4 Heterolysis of Bonds to Carbon: Carbocations and Carbanions 104

THE CHEMISTRY OF . . . HOMOs and LUMOs in Reactions 105

3.5 How to Use Curved Arrows in Illustrating Reactions 106

3.6 The Strength of Acids and Bases: Ka and pKa 109

3.7 How to Predict  the Outcome of Acid-Base Reactions 113

3.8 Relationships between Structure and Acidity 115

3.9 Energy Changes 119

3.10 The Relationship between the Equilibrium Constant and the Standard Free-Energy

Change, ΔG° 120

3.11 The Acidity of Carboxylic Acids 121

3.12 The Effect of the Solvent on Acidity 125

3.13 Organic Compounds as Bases 126

3.14 A Mechanism for an Organic Reaction 127

THE CHEMISTRY OF . . . Carbonic Anhydrase

3.15 Acids and Bases in Nonaqueous Solutions 128

3.16 Acid-Base Reactions and the Synthesis of Deuterium- and Tritium-Labeled Compounds 130

3.17 Applications of Basic Principles 131

4 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 137

4.1 Introduction to Alkanes and Cycloalkanes 138

THE CHEMISTRY OF . . . Petroleum Refining 139

4.2 Shapes of Alkanes 140

4.3 IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols 142

4.4 How to Name Cycloalkanes  149

4.5 Nomenclature of Alkenes and Cycloalkenes 151

4.6 Nomenclature of Alkynes 154

4.7 Physical Properties of Alkanes and Cycloalkanes 154

THE CHEMISTRY OF . . . Pheromones: Communication by Means of Chemicals 156

4.8 Sigma Bonds and Bond Rotation 157

4.9 Conformational Analysis of Butane 160

THE CHEMISTRY OF . . . Muscle Action 162

4.10 The Relative Stabilities of Cycloalkanes: Ring Strain 162

4.11 Conformations of Cyclohexane: The Chair and the Boat 163

THE CHEMISTRY OF . . . Nanoscale Motors and Molecular Switches 166

4.12 Substituted Cyclohexanes: Axial and Equatorial Hydrogen Atoms 167

4.13 Disubstituted Cycloalkanes: Cis-Trans Isomerism 171

4.14 Bicyclic and Polycyclic Alkanes 175

THE CHEMISTRY OF . . . Elemental Carbon 176

4.15 Chemical Reactions of Alkanes 177

4.16 Synthesis of Alkanes and Cycloalkanes 177

4.17 How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency 178

4.19 Applications of Basic Principles 181

5 STEREOCHEMISTRY: Chiral Molecules 186

5.1 Chirality and Stereochemistry 186

5.2 Isomerism: Constitutional Isomers and Stereoisomers 188

5.3 Enantiomers and Chiral Molecules 190

5.4 A Single Chirality Center Causes a Molecule to Be Chiral 191

THE CHEMISTRY OF . . .Life's Molecular Handedness 193

5.5 More about the Biological Importance of Chirality 194

5.6 How to Test for Chirality: Planes of Symmetry 195

5.7 Naming Enantiomers: The R,S-System 196

5.8 Properties of Enantiomers: Optical Activity 201

5.9 The Origin of Optical Activity 205

5.10 The Synthesis of Chiral Molecules 207

5.11 Chiral Drugs 209

THE CHEMISTRY OF . . . Selective Binding of Drug Enantiomers to Left- and Right-Handed Coiled DNA 211

5.12 Molecules with More than One Chirality Center 211

5.13 Fischer Projection Formulas 215

5.14 Stereoisomerism of Cyclic Compounds 217

5.15 Relating Configurations through Reactions in Which No Bonds to the Chirality Center Are Broken  219

5.16 Separation of Enantiomers: Resolution 223

5.17 Compounds with Chirality Centers Other than Carbon 224

5.18 Chiral Molecules that Do Not Possess a Chirality Center 224

6 IONIC REACTIONS: Nucleophilic Substitution and Elimination Reactions of Alkyl Halides 230

6.1 Organic Halides 231

6.2 Nucleophilic Substitution Reactions 233

6.3 Nucleophiles 234

6.4 Leaving Groups 237

6.5 Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction 237

6.6 A Mechanism for the SN2 Reaction 238

6.7 Transition State Theory: Free-Energy Diagrams 240

6.8 The Stereochemistry of SN2 Reactions 243

THE CHEMISTRY OF . . . Lysozyme

6.9 The Reaction of tert-Butyl Chloride with Hydroxide Ion: An SN1 Reaction 246

6.10 A Mechanism for the SN1 Reaction 247

6.11 Carbocations 248

6.12 The Stereochemistry of SN1 Reactions 251

6.13 Factors Affecting the Rates of SN1 and SN2 Reactions 254

6.14 Organic Synthesis: Functional Group Transformations Using SN2 Reactions 264

THE CHEMISTRY OF . . . Biological Methylation: A Biological Nucleophilic Substitution Reaction 266

6.15 Elimination Reactions of Alkyl Halides 268

6.16 The E2 Reaction 269

6.17 The E1 Reaction 271

6.18 How to Determine whether Substitutions or Elimination Is Favored 273

6.19 Overall Summary 276

7 ALKENES AND ALKYNES I: Properties and Synthesis. Elimination Reactions of Alkyl Halides 285

7.1 Introduction 286

7.2 The (E)-(Z) System for Designating Alkene Diastereomers 286

7.3 Relative Stabilities of Alkenes 288

7.4 Cycloalkenes 290

7.5 Synthesis of Alkenes via Elimination Reactions 291

7.6 Dehydrohalogenation of Alkyl Halides 291

7.7 Acid-Catalyzed Dehydration of Alcohols 297

7.8 Carbocation Stability and the Occurrence of Molecular Rearrangements 303

7.9 The Acidity of Terminal Alkynes 307

7.10 Synthesis of Alkynes by Elimination Reactions 308

7.11 Replacement of the Acetylenic Hydrogen Atom of Terminal Alkynes 310

7.12 Alkylation of Alkynide Anions: Some General Principles of Structure and Reactivity Illustrated 312

7.13 Hydrogenation of Alkenes 313

THE CHEMISTRY OF . . . Hydrogenation in the Food Industry 313

7.14 Hydrogenation: The Function of the Catalyst 314

7.15 Hydrogenation of Alkynes 315

7.16 An Introduction to Organic Synthesis  317

THE CHEMISTRY OF . . . From the Inorganic to the Organic 321

8 ALKENES AND ALKYNES II: Addition Reactions 331

8.1 Addition Reactions of Alkenes 332

8.2 Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov's Rule 334

8.3 Stereochemistry of the Ionic Addition to an Alkene 339

8.4 Addition of Sulfuric Acid to Alkenes 340

8.5 Addition of Water to Alkenes: Acid-Catalyzed Hydration 340

8.6 Alcohols from Alkenes through Oxymercuration-Demercuration: Markovnikov Addition 344

8.7 Alcohols from Alkenes through Hydroboration-Oxidation: Anti-Markovnikov Syn Hydration 347

8.8 Hydroboration: Synthesis of Alkylboranes 347

8.9 Oxidation and Hydrolysis of Alkyboranes 350

8.10 Summary of Alkene Hydration Methods 353

8.11 Protonolysis of Alkyboranes 353

8.12 Electrophilic Addition of Bromine and Chlorine to Alkenes 354

THE CHEMISTRY OF . . .The Sea: A Treasure of Biologically Active Natural Products 357

8.13 Stereospecific Reactions 358

8.14 Halohydrin Formation 359

8.15 Divalent Carbon Compounds: Carbenes 361

8.16 Oxidations of Alkenes: Syn 1,2-Dihydroxylation 363

THE CHEMISTRY OF . . . Catalytic Asymmetric Dihydroxylation 365

8.17 Oxidative Cleavage of Alkenes 365

8.18 Electrophilic Addition of Bromine and Chlorine to Alkynes 368

8.19 Addition of Hydrogen Halides to Alkynes 369

8.20 Oxidative Cleavage of Alkynes 370

8.21 How to Plan a Synthesis: Some Approaches and Examples 370

9 NUCLEAR MAGNETIC RESONANCE AND MASS SPECTROMETRY: Tools for Structure Determination 385

9.1 Introduction 386

9.2 Nuclear Magnetic Resonance (NMR) Spectroscopy 386

9.3 How to Interpret Proton NMR Spectra 392

9.4 Nuclear Spin: The Origin of the Signal 395

9.5 Detecting the Signal: Fourier Transform NMR Spectrometers 397

9.6 Shielding and Deshielding of Protons 399

9.7 The Chemical Shift 400

9.8 Chemical Shift Equivalent and Nonequivalent Protons 401

9.9 Signal Splitting: Spin-Spin Coupling 405

9.10 Proton NMR Spectra and Rate Processes 415

9.11 Carbon-13 NMR Spectroscopy 417

9.12 Two-Dimensional (2D) NMR Techniques 422

THE CHEMISTRY OF . . . Magnetic Resonance Imaging in Medicine 425

9.13 An Introduction to Mass Spectrometry 426

9.14 Formation of Ions: Electron Impact Ionization 427

9.15 Depicting the Molecular Ion 427

9.16 Fragmentation 428

9.17 How to Determine Molecular Formulas and Molecular Weights Using Mass Spectrometry 435

9.18 Mass Spectrometer Instrument Designs 440

9.19 GC/MS Analysis 442

9.20 Mass Spectrometry of Biomolecules 443

10 RADICAL REACTIONS 459

10.1 Introduction: How Radicals Form and How They React 460

10.2 Homolytic Bond Dissociation Energies (DH°) 461

10.3 The Reactions of Alkanes with Halogens 465

10.4 Chlorination of Methane: Mechanism of Reaction 467

10.5 Chlorination of Methane: Energy Changes 470

10.6 Halogenation of Higher Alkanes 477

10.7 The Geometry of Alkyl Radicals 480

10.8 Reactions that Generate Tetrahedral Chirality Centers 481

10.9 Radical Addition to Alkenes: The Anti-Markovnikov Addition of Hydrogen Bromide 484

10.10 Radical Polymerization of Alkenes: Chain-Growth Polymers 486

10.11 Other Important Radical Reactions 490

THE CHEMISTRY OF . . . Calicheamicin λ11: A Radical Device for Slicing the Backbone of DNA 492

THE CHEMISTRY OF . . . Antioxidants 494

THE CHEMISTRY OF . . . Ozone Depletion and Chlorofluorocarbons (CFCs) 495

11 ALCOHOLS AND ETHERS 502

11.1 Structure and Nomenclature 503

11.2 Physical Properties of Alcohols and Ethers 505

11.3 Important Alcohols and Ethers 507

THE CHEMISTRY OF . . . Ethanol as a Biofuel 508

11.4 Synthesis of Alcohols from Alkenes 508

11.5 Reactions of Alcohols 511

11.6 Alcohols as Acids 513

11.7 Conversion of Alcohols into Alkyl Halides 514

11.8 Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides 514

11.9 Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCl2 517

11.10 Tosylates, Mesylates, and Triflates: Leaving Group Derivatives of Alcohols 518

THE CHEMISTRY OF . . . Alkyl Phosphates 521

11.11 Synthesis of Ethers 522

11.12 Reactions of Ethers 527

11.13 Epoxides 528

THE CHEMISTRY OF . . . The Sharpless Asymmetric Epoxidation 529

11.14 Reactions of Epoxides 531

THE CHEMISTRY OF . . . Epoxides, Carcinogens, and Biological Oxidation 533

11.15 Anti 1,2-Dihydroxylation of Alkenes via Epoxides 535

THE CHEMISTRY OF . . . Environmentally Friendly Alkene Oxidation Methods 537

11.16 Crown Ethers 537

THE CHEMISTRY OF . . . Transport Antibiotics and Crown Ethers 539

11.17 Summary of Reactions of Alkenes, Alcohols, and Ethers 540

12 ALCOHOLS FROM CARBONYL COMPOUNDS: Oxidation-Reduction and Organometallic Compounds 548

12.1 Structure of the Carbonyl Group 549

12.2 Oxidation-Reduction Reactions in Organic Chemistry 550

12.3 Alcohols by Reduction of Carbonyl Compounds 552

THE CHEMISTRY OF . . . Alcohol Dehydrogenase - A Bioehcmical Hydride Reagent 554

THE CHEMISTRY OF . . . Stereoselective Reductions of Carbonyl Groups 555

12.4 Oxidation of Alcohols 557

12.5 Organometallic Compounds 561

12.6 Preparation of Organolithium and Organomagnesium Compounds 562

12.7 Reactions of Organolithium and Organomagnesium Compounds 563

12.8 Alcohols from Grignard Reagents 566

12.9 Protecting Groups 575

CONJUGATED UNSATURATED SYSTEMS 585

13.1 Introduction 586

13.2 Allylic Substitution and the Allyl Radical 586

THE CHEMISTRY OF . . . Allylic Bromination 590

13.3 The Stability of the Allyl Radical 590

13.4 The Allyl Cation 594

13.5 Resonance Theory Revisited 595

13.6 Alkadienes and Polyunsaturated Hydrocarbons 599

13.7 1,3-Butadiene: Electron Delocalization 600

13.8 The Stability of Conjugated Dienes 602

13.9 Ultraviolet-Visible Spectroscopy 604

THE CHEMISTRY OF . . . The Photochemistry of Vision 609

13.10 Electrophilic Attack on Conjugated Dienes: 1,4 Addition 612

13.11 The Diels-Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes 616

THE CHEMISTRY OF . . . Molecules with the Nobel Prize in Their Synthetic Lineage 620

14 AROMATIC COMPOUNDS 632

14.1 The Discovery of Benzene 633

14.2 Nomenclature of Benzene Derivatives 634

14.3 Reactions of Benzene 637

14.4 The Kekulé Structure for Benzene 638

14.5 The Thermodynamic Stability of Benzene 639

14.6 Modern Theories of the Structure of Benzene 640

14.7 Hückel's Rule: The 4n + 2 π Electron Rule 643

14.8 Other Aromatic Compounds 651

THE CHEMISTRY OF . . . Nanotubes 655

14.9 Heterocylic Aromatic Compounds 655

14.10 Aromatic Compounds in Biochemistry 657

14.11 Spectroscopy of Aromatic Compounds 660

THE CHEMISTRY OF . . . Sunscreens (Catching the Sun's Rays and What Happens to Them) 664

15 REACTIONS OF AROMATIC COMPOUNDS 676

15.1 Electrophilic Aromatic Substitution Reactions 677

15.2 A General Mechanism for Electrophilic Aromatic Substitution 678

15.3 Halogenation of Benzene 680

15.4 Nitration of Benzene 681

15.5 Sulfonation of Benzene 682

15.6 Friedel-Crafts Alkylation 684

15.7 Friedel-Crafts Acylation 685

15.8 Limitations of Friedel-Crafts Reactions 687

15.9 Synthetic Applications of Friedel-Crafts Acylations: The Clemmensen Reduction 690

15.10 Substituents Can Affect Both the Reactivity of the Ring and the Orientation of the Incoming Group 691

15.11 How Substituents Affect Electrophilic Aromatic Substitution: A Closer Look 697

15.12 Reactions of the Side Chain of Alkylbenzenes 706

THE CHEMISTRY OF . . . Iodine Incorporation in Thyroxine Biosynthesis 707

THE CHEMISTRY OF . . . Industrial Styrene Synthesis 709

15.13 Alkenylbenzenes 712

15.14 Synthetic Applications 714

15.15 Allylic and Benzylic Halides in Nucleophilic Substitution Reactions 717

15.16 Reduction of Aromatic Compounds 719   

16 ALDEHYDES AND KETONES: Nucleophilic Addition to the Carbonyl Group 729

16.1 Introduction 730

16.2 Nomenclature of Aldehydes and Ketones 730

16.3 Physical Properties 732

THE CHEMISTRY OF . . . Aldehydes and Ketones in Perfumes 733

16.4 Synthesis of Aldehydes 733

16.5 Synthesis of Ketones 738

16.6 Nucleophilic Addition to the Carbon-Oxygen Double Bond 741

16.7 The Addition of Alcohols: Hemiacetals and Acetals 744

16.8 The Addition of Primary and Secondary Amines 751

THE CHEMISTRY OF . . . A Very Versatile Vitamin, Pyridoxine (Vitamin B6) 753

16.9 The Addition of Hydrogen Cyanide: Cyanohydrins 755

16.10 The Addition of Ylides: The Wittig Reaction 757

16.11 Oxydation of Aldehydes 761

16.12 Chemical Analyses for Aldehydes and Ketones 761

16.13 Spectroscopic Properties of Aldehydes and Ketones 762

16.14 Summary of Aldehyde and Ketone Addition Reactions 765

17 CARBOXYLIC ACIDS AND THEIR DERIVATIVES: Nucleophilic Addition-Elimination at  the Acyl Carbon 779

17.1 Introduction 780

17.2 Nomenclature and Physical Properties 780

17.3 Preparation of Carboxylic Acids 789

17.4 Acyl Substitution: Nucleophilic Addition-Elimination at the Acyl Carbon 792

17.5 Acyl Chlorides 794

17.6 Carboxylic Acid Anhydrides 796

17.7 Esters 797

17.8 Amides 804

THE CHEMISTRY OF . . . Penicillins 811

17.9 Derivatives of Carbonic Acid 812

17.10 Decarboxylation of Carboxylic Acids 814

17.11 Chemical Tests for Acyl Compounds 816

17.12 Polyesters and Polyamides: Step-Growth Polymers 817

17.13 Summary of the Reactions of Carboxylic Acids and Their Derivatives 818

18 REACTIONS AT THE α  CARBON OF CARBONYL COMPOUNDS: Enols and Enolates 831

18.1 The Acidity of the α Hydrogens of Carbonyl Compounds: Enolate Anions 832

18.2 Keto and Enol Tautomers 833

18.3 Reactions via Enols and Enolates 834

THE CHEMISTRY OF . . . Chloroform in Drinking Water 839

18.4 Lithium Enolates 841

18.5 Enolates of  β-Dicarbonyl Compounds 844

18.6 Synthesis of Methyl Ketones: The Acetoacetic Ester Snythesis 845

18.7 Synthesis of Substituted Acetic Acids: The Malonic Ester Synthesis 856

18.8 Further Reactions of Active Hydrogen Compounds 853

18.9 Synthesis of Enamines: Stork Enamine Reactions 854

18.10 Summary of Enolate Chemistry 857

19 CONDENSATION AND CONJUGATE ADDITION REACTIONS OF CARBONYL COMPOUNDS: More Chemistry of Enolates 869

19.1 Introduction 870

19.2 The Claisen Condensation: The Synthesis of β-Keto Esters 870

19.3 β-Dicarbonyl Compounds by Acylation of Ketone Enolates 875

19.4 Aldol Reactions: Addition of Enolates and Enols to Aldehydes and Ketones 876

THE CHEMISTRY OF . . .A Retro-Aldol Reaction in Glycolysis-Dividing Assets to Double the ATP Yield 878

19.5 Crossed Aldol Condensations 882

19.6 Cyclizations via Aldol Condensations 888

19.7 Additions to α,β-Unsaturated Aldehydes and Ketones 889

THE CHEMISTRY OF . . .  Calicheamicin γ11 Activation for Cleavage of DNA 894

19.8 The Mannich Reaction 894

THE CHEMISTRY OF . . . A Suicide Enzyme Substrate 895

19.9 Summary of Important Reactions 897

20 AMINES 911

20.1 Nomenclature 912

20.2 Physical Properties and Structure of Amines 913

20.3 Basicity of Amines: Amine Salts 915

THE CHEMISTRY OF . . . Biologically Important Amines 922

20.4 Preparation of Amines 924

20.5 Reactions of Amines 933

20.6 Reactions of Amines with Nitrous Acid 935

THE CHEMISTRY OF . . . N-Nitrosoamines 936

20.7 Replacement Reactions of Arenediazonium Salts 937

20.8 Coupling Reactions of Arenediazonium Salts 941

20.9 Reactions of Amines with Sulfonyl Chlorides 943

THE CHEMISTRY OF . . . Chemotherapy and Sulfa Drugs 944

20.10 Synthesis of Sulfa Drugs 947

20.11 Analysis of Amines 947

20.12 Eliminations Involving Ammonium Compounds 949

20.13 Summary of Preparations and Reactions of Amines 950

21 PHENOLS AND ARYL HALIDES: Nucleophilic Aromatic Substitution  964

21.1 Structure and Nomenclature of Phenols 965

21.2 Naturally Occurring Phenols 966

21.3 Physical Properties of Phenols 966

21.4 Synthesis of Phenols 967

21.5 Reactions of Phenols as Acids 969

21.6 Other Reactions of the O-H Group of Phenols 972

21.7 Cleavage of Alkyl Aryl Ethers 973

21.8 Reactions of the Benzene Ring of Phenols 973

THE CHEMISTRY OF . . . Polyketide Anticancer Antibiotic Biosynthesis 975

21.9 The Claisen Rearrangement 977

21.10 Quinones 978

THE CHEMISTRY OF . . . The Bombardier Beetle's Noxious Spray 979

21.11 Aryl Halides and Nucleophilic Aromatic Substitution 980

THE CHEMISTRY OF . . . Bacterial Dehalogenation of a PCB Derivative 983

21.12 Spectroscopic Analysis of Phenols and Aryl Halides 988

THE CHEMISTRY OF . . . Aryl Halides: Their Uses and Environmental Concerns 989

22 CARBOHYDRATES 1000

22.1 Introduction 1001

22.2 Monosaccharides 1004

22.3 Mutarotation 1009

22.4 Glycoside Formation 1010

22.5 Other Reactions of Monosaccharides 1013

22.6 Oxidation Reactions of Monosaccharides 1016

22.7 Reduction of Monosaccharides: Alditols 1022

22.8 Reactions of Monosaccharides with Phenylhydrazine: Osazones 1022

22.9 Synthesis and Degradation of Monosaccharides 1023

22.10 The D Family of Aldoses 1025

22.11 Fischer's Proof of the Configuration of D-(+)-Glucose 1027

22.12 Disaccharides 1029

THE CHEMISTRY OF . . . Artificial Sweeteners (How Sweet It Is) 1032

22.13 Polysaccharides 1033

22.14 Other biologically Important Sugars 1037

22.15 Sugars That Contain Nitrogen 1038

22.16 Glycolipids and Glycoproteins of the Cell Surface: Cell Recognition and the Immune System 1040

22.17 Carbohydrate Antibiotics 1042

22.18 Summary of Reactions of Carbohydrates 1042

23 LIPIDS 1050

23.1 Introduction 1051

23.2 Fatty Acids and Triacylglycerols 1052

THE CHEMISTRY OF . . . Olestra and Other Fat Substitutes 1055

THE CHEMISTRY OF . . . Self-Assembled Monolayers-Lipids in Materials Science and

Bioengineering  1060

23.3 Terpenes and Terpenoids 1061

23.4 Steroids 1064

23.5 Prostaglandins 1073

23.6 Phospholipids and Cell Membranes 1074

THE CHEMISTRY OF . . . STEALTH Liposomes for Drug Delivery 1077

23.7 Waxes 1078

24 AMINO ACIDS AND PROTEINS 1084

24.1 Introduction 1085

24.2 Amino Acids 1086

24.3 Synthesis of α-Amino Acids 1092

24.4 Polypeptides and Proteins 1094

24.5 Primary Structure of Polypeptides and Proteins 1097

24.6 Examples of Polypeptide and Protein Primary Structure 1101

THE CHEMISTRY OF . . . Sickle-Cell Anemia 1103

24.7 Polypeptide and Protein Synthesis 1104

24.8 Secondary, Tertiary, and Quaternary Structure of Proteins 1110

24.9 Introduction to Enzymes 1115

24.10 Lysozyme: Mode of Action of an Enzyme 1116

THE CHEMISTRY OF . . . Carbonic Anhydrase: Shuttling the Protons 1119

24.11 Serine Proteases  1120

24.12 Hemoglobin: A Conjugated Protein 1122

THE CHEMISTRY OF . . . Some Catalytic Antibodies 1123

24.13 Purification and Analysis of Polypeptides and Proteins 1125

24.14 Proteomics 1126

25 NUCLEIC ACIDS AND PROTEIN SYNTHESIS 1131

25.1 Introduction 1132

25.2 Nucleotides and Nucleosides 1133

25.3 Laboratory Synthesis of Nucleosides and Nucleotides 1137

25.4 Deoxyribonucleic Acid: DNA 1139

25.5 RNA and Protein Synthesis 1146

25.6 Determining the Base Sequence of DNA: The Chain-Terminating (Dideoxynucleotide) Method 1155

25.7 Laboratory Synthesis of Oligonucleotides 1157

25.8 The Polymerase Chain Reaction 1158

25.9 Sequencing of the Human Genome: An Instruction Book for the Molecules of Life 1162

1 The Basics Bonding and Molecular Structure.

2 Families of Carbon Compounds Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy.

3 An Introduction to Organic Reactions and Their Mechanisms Acids and Bases.

4 Nomenclature and Conformations of Alkanes and Cycloalkanes.

5 Stereochemistry Chiral Molecules.

6 Ionic Reactions Nucleophilic Substitution and Elimination Reactions of Alkyl Halides.

7 Alkenes and Alkynes I Properties and Synthesis. Elimination Reactions of Alkyl Halides.

8 Alkenes and Alkynes II Addition Reactions.

9 Nuclear Magnetic Resonance and Mass Spectrometry Tools for Structure Determination.

10 Radical Reactions.

11 Alcohols and Ethers Synthesis and Reactions.

12 Alcohols From Carbonyl Compounds Oxidation–Reduction and Organometallic Compounds.

13 Conjugated Unsaturated Systems.

14 Aromatic Compounds.

15 Reactions of Aromatic Compounds.

16 Aldehydes and Ketones Nucleophilic Addition to the Carbonyl Group.

17 Carboxylic Acids and Their Derivatives Nucleophilic Addition–Elimination at the Acyl Carbon.

18 Reactions at the a Carbon of Carbonyl Compounds Enols and Enolates.

19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds More Chemistry of Enolates.

20 Amines.

21 Phenols and Aryl Halides Nucleophilic Aromatic Substitution.

Special Topic G Carbon-Carbon Bond-Forming and Other Reactions of Transition Metal Organometallic Compounds.

22 Carbohydrates.

23 Lipids.

24 Amino Acids and Proteins.

25 Nucleic Acids and Protein Synthesis.

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Content Changes to This Edition:
  • Chapters on carbonyl chemistry have been reorganized along mechanistic themes and with an emphasis on current synthetic techniques.   
  • New coverage of modern organometallic carbon-carbon bond forming reactions is included in the 10th edition. 
  • Special Topics are included at www.wileyplus.com for areas such as polymers, biosynthesis, electrocyclic reactions, and others. 

Pedagogical Changes to This Edition:

  • A focus on the essential. We have made fundamental revisions to our presentation of information to help students focus on what is essential in Organic Chemistry. Key ideas have been indicated by bullet points throughout the text to help students focus on the most important aspects of Organic Chemistry.  
  • How To sections within the chapters give step-by-step instructions to guide students in performing important tasks such as determining formal charges, writing Lewis structures, interpreting 13C spectra and using 1H NMR to determine structure.
  • Approximately 200 new Solved Problems guide students in their approaches to solving problems as they move through each chapter Subsequent in-chapter Review Problems then allow students to check their understanding of each new idea as they encounter it.  
  • Approximately 300 new end-of-chapter exercises, many of which are based on bond-line structural formulas instead of chemical names.
    • The end-of-chapter problems have been grouped and labeled according to their content and function.
    • The visual nature of problem-solving in organic chemistry has been emphasized by the recasting of many problems in a structure-based rather than a text-based format.  
  • New, streamlined chapter openers with photos introduce students to the topics and concepts to be covered in the chapter, and include applications from everyday life that will serve to pique student interest.  These applications are often revisited later in the chapter.
  • Mechanism for the Reaction boxes are catalogued in the front matter of the book, providing easy reference access for students. 
  • Completely revised and updated test bank.
  • Rich online teaching and learning solution delivered through WileyPLUS w/Catalyst.
    • Includes an e-book, rich assessment material (end of chapter exercises have been coded into WileyPLUS, alongside a database of over 25,000 mastery style questions called CATALYST) that includes many molecular drawing questions (MarvinSketch), and a gradebook . 
    • Clicker questions are also provided to support interactive styles of classroom teaching   
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  • A balanced approach – the text organization blends features of a  functional group approach with one based on reaction mechanisms. 
  • The study of mechanisms begins early in the context of acid-base chemistry. 
  • Mechanism of the Reaction boxes throughout the book explain in detail everything a student needs to know about a reaction mechanism. 
  • An emphasis on problem solving and critical thinking, key to helping students successfully meet the science and technology needs of the future.   
  • Coverage of topics in green chemistry, nanotechnology, and biochemistry to introduce students to exciting and important frontiers of organic chemistry.
  • The inclusion of “Chemistry Of” boxes present examples of biological and real-world chemistry that help students relate organic chemistry to the world around them.
  • Early introduction of infrared spectroscopy to give students evidence for functional groups and structure, and supports their use of instrumentation in laboratory classes.
  • Tools such as Concept Maps, Synthetic Connections, and Mechanism Reviews summarize key information for students at the end of chapters
  • Learning Group Problems facilitate active and collaborative student involvement in learning.
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Instructors Resources
Wiley Instructor Companion Site
Computerized Test Bank
Test items in either IBM or MAC formats.
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Students Resources
Wiley Student Companion Site
Computerized Test Bank
Test items in either IBM or MAC formats.
Available Materials
by T. W. Graham Solomons, Craig B. Fryhle
978-0-470-47839-4
February 2010, ©2011, Paperback (E-book also available)
ADDITIONAL RESOURCES
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CourseSmart
Instant access to textbooks as eTextbooks.
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Wiley E-Text   
Organic Chemistry, Student Study Guide and Student Solutions Manual , 10th Edition
ISBN : 978-0-470-60589-9
July 2010, ©2011
$71.50   BUY

Wiley E-Text   
Organic Chemistry, 10th Edition
ISBN : 978-0-470-56377-9
February 2010, ©2011
$103.50   BUY

Paperback   
Student Study Guide and Student Solutions Manual to Accompany Organic Chemistry 10th Edition Binder Ready Version
ISBN : 978-0-470-87638-1
744 pages
May 2010, ©2011
$129.95   BUY

Paperback   
Student Study Guide and Student Solutions Manual to accompany Organic Chemistry 10th Edition Binder Ready Version with Binder Set
ISBN : 978-0-470-87666-4
744 pages
March 2010, ©2011
$136.95   BUY

Loose-leaf   
Organic Chemistry, 10th Edition Binder Ready Version
ISBN : 978-0-470-55659-7
1328 pages
December 2009, ©2011
$197.95   BUY

Hardcover   
Organic Chemistry, 10th Edition
ISBN : 978-0-470-40141-5
1272 pages
December 2009, ©2011
$282.95   BUY

Hardcover   
Organic Chemistry 10th Edition with Student Study Guide/Solutions Manual Set
ISBN : 978-0-470-61068-8
November 2009, ©2011
$457.95   BUY

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