国外名校名著 有机化学 第8版 英文影印版2025|PDF|Epub|mobi|kindle电子书版本百度云盘下载

国外名校名著 有机化学 第8版 英文影印版PDF格式电子书版下载

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chapter 1 Carbon Compounds and Chemical Bonds1

“We Are Slardust”1（Molecular graphic：Glycine，an organic molecule found in space）2

1.1 Introduction2

1.2 The Development of Organic Chemistry as a Science3

1.3 The Structural Theory of Organic Chemistry4

1.4 Chemical Bonds：The Octet Rule6

1.5 Writing Lewis Structures8

1.6 Exceptions to the Octet Rule10

1.7 Formal Charge11

1.8 Resonance14

1.9 Quantum Mechanics19

1.10 Atomic Orbitals20

1.11 Molecular Orbitals22

1.12 The Structure of Methane and Ethane：sp3 Hybridization25

The Chemistry of...Calculated Molecular Models：Electron Density Surfaces29

1.13 The Structure of Ethene（Ethylene）：sp2 Hybridization29

1.14 The Structure of Ethyne（Acetylene）：sp Hybridization34

1.15 A Summary of Important Concepts that Come From Quantum Mechanics36

1.16 Molecular Geometry：The Valence Shell Electron Pair Repulsion Model38

1.17 Representation of Structural Formulas41

Chapter 2 Representative Carbon Compounds：Functional Groups,Intermolecular Forces,and Infrared（IR）Spectroscopy52

Structure and Function：Organic Chemistry,Nanotechnology,and Bioengineering（Molecular graphic：A molecular template for bone growth）52

2.1 Carbon-Carbon Covalent Bonds53

2.2 Hydrocarbons：Representative Alkanes，Alkenes，Alkynes，and Aromatic Compounds53

2.3 Polar Covalent Bonds56

The Chemistry of... calculated Molecular Models：Maps of Electrostatic Potentlal58

2.4 Polar and Nonpolar Molecules59

2.5 Functional Groups61

2.6 Alkyl Halides or Haloalkanes63

2.7 Alcohols63

2.8 Ehers65

2.9 Amines66

2.10 Aldehydes and Ketones67

2.11 Carboxylic Acids，Esters，and Amides68

2.12 Nitriles69

2.13 Summary of Important Families of Organic Compounds70

2.14 Physical Properties and Molecular Structure70

2.15 Summary of Attractive Electric Forces78

The Chemistry of... Organic Templates Engineered to Mimic Bone Growth78

2.16 Infrared Spectroscopy：An Instrumental Method for Detecting Functional Groups79

Chapter 3 An Introdution to Organic Reactions：ACIds and Bases94

Shuttling the Protons（Molecular graphic：Diamox，a drug that prevents altitude sickness）94

3.1 Reactions and Their Mechanisms95

3.2 Acid-Base Reactions97

The Chemistry of...HOMOs and LUMOs in Reactions101

3.3 Heterolysis of Bonds to Carbon：Carbocations and Carbanions101

3.4 The Use of Curved Arrows in Illustrating Reactions102

3.5 The Strength of Acids and Bases：Ka and pKa104

3.6 Predicting the Outcome of Acid-Base Reactions107

3.7 The Relationship Between Structure and Acidity109

3.8 Energy Changes113

3.9 The Relationship Between the Equilibrium Constant and the Standard Free-Energy Change， △G°114

3.10 The Acidity of Carboxylic Acids115

3.11 The Effect of the Solvent on Acidity120

3.12 Organic Compounds as Bases121

3.13 A Mechanism for an Organic Reaction122

The Chemistry of...Carbonic Anhydrase124

3.14 Acids and Bases in Nonaqueous Solutions124

3.15 Acid-Base Reactions and the Synthesis of Deuterium-and Tritium-Labeled Compounds126

Chapter 4 Alkanes：Nomenclature,Conformational Analysis,and an Introduction to Synthesis134

To Be Flexible or inflexible-Molecular Structure Makes the Difference（Molecular graphic：A portion of the structure of diamond，an exceptionally rigid molecule）134

4.1 Introduction to Alkanes and Cycloalkanes135

4.2 Shapes of Alkanes137

4.3 IUPAC Nomenclature of Alkanes，Alkyl Halides，and Alcohols139

4.4 Nomenclature of Cycloalkanes147

4.5 Nomenclature of Alkenes and Cycloalkenes150

4.6 Nomenclature of Alkynes152

4.7 Physical Properties of Alkanes and Cycloalkanes152

4.8 Sigma Bonds and Bond Rotation154

4.9 Conformational Analysis of Butane157

4.10 The Relative Stabilities of Cycloalkanes：Ring Strain159

4.11 The Origin of Ring Strain in Cyclopropane and Cyclobutane：Angle Strain and Torsional Strain162

4.12 Conformations of Cyclohexane163

The Chemistry of…Nanoscale Motors and Molecular Switches166

4.13 Substituted Cyclohexanes：Axial and Equatorial Hydrogen Atoms167

4.14 Disubstituted Cycloalkanes：Cis-Trans Isomerism171

4.15 Bicyclic and Polycyclic Alkanes175

The Chemistry of…Pheromones：Communication by Means of Chemicals177

4.16 Chemical Reactions of Alkanes177

4.17 Synthesis of Alkanes and Cycloalkanes178

4.18 Some General Principles of Structure and Reactivity： A Look toward Synthesis180

4.19 An Introduction to Organic Synthesis181

The Chemistry of…From the Inorganic to Organic185

Chapter 5 Stereochemistry：Chhiral Molecules193

The Handedness of Life（Molecular graphic：The mirror-image stereoisomners of alanine，a chiral amino acid）193

5.1 The Biological Significance of Chirality194

5.2 Isomerism：Constitutional Isomers and Stereoisomers195

5.3 Enantiomers and Chiral Molecules196

5.4 More about the Biological Importance of Chirality200

5.5 Historical Origin of Stereochemist201

5.6 Tests for Chirality： Planes of Symmetry202

5.7 Nomenclature of Enantiomers：The R，S System203

5.8 Properties of Enantiomers：Optical Activity208

5.9 The Origin of Optical Activity212

5.10 The Synthesis of Chiral Molecules215

5.11 Chiral Drugs217

The Chemmistry of…Selective Binding of Drug Enantiomers to Left-and Right-Hand Coiled DNA218

5.12 Molecules with More than One Stereogenic Center219

5.13 Fischer Projection Formulas223

5.14 Stereoisomerism of Cyclic Compounds224

5.15 Relating Configurations Through Reactions in Which No Bonds to the Stereogenic Carbon Are Broken227

5.16 Separation of Enantiomers：Resolution230

5.17 Compounds with Stereogenic Centers Other than Carbon231

5.18 Chiral Molecules that Do Not Possess a Tetrahedral Atom with Four Different Groups231

Chapter 6 Ionic Reactions—Nucleophilic Substitution and Elimination Reactions of Alkyl Halides238

Breaking Bacterlal Cell Walls with Organic Chemistrry（Molecular graphic：The SN2 transition state resulting from collision of a hydroxide anion with chloromethane）238

6.1 Introduction239

6.2 Nucleophilic Substitution Reactions241

6.3 Nucleophiles241

6.4 Leaving Groups242

6.5 Kinetics of a Nucleophilic Substitution Reaction：An SN2 Reaction243

6.6 A Mechanism for the SN2 Reaction244

6.7 Transition State Theory：Free-Energy Diagrams245

6.8 The Stereochemistry of SN2 Reactions249

6.9 The Reaction of tert-Butyl Chloride with Hydroxide Ion：An SN1 Reaction251

6.10 A Mechanism for the SN1 Reaction252

6.11 Carbocations254

6.12 The Stereochemistry of SN1 Reactions256

6.13 Factors Affecting the Rates of SN1 and SN2 Reactions258

6.14 Organic Synthesis：Functional Group Transformations Using SN2 Reactions267

The Chemistry of…Biological Methylation：A Biological Nucleophilic Substitution Reaction268

6.15 Elimination Reactions of Alkyl Halides271

6.16 The E2 Reaction273

6.17 The E1 Reaction274

6.18 Substitution versus Elimination275

6.19 Overall Summary278

Chapter 7 Alkenes and AHkynesⅠ：Properties and Synthesis.Elimination Reactions of Alkyl Halides287

Cell Membrane Fluidity（Molecular graphic：cis-9-Octadecenoic acid，an unsaturated fatty acid incorporated into cell membrane phospholipids）287

7.1 Introduction288

7.2 The（E）-（Z）System for Designating Alkene Diastereomers288

7.3 Relative Stabilities of Alkenes290

7.4 Cycloalkenes292

7.5 Synthesis of Alkenes via Elimination Reactions292

7.6 Dehydrohalogenation of Alkyl Halides293

7.7 Acid-Catalyzed Dehydration of Alcohols298

7.8 Carbocation Stability and the Occurrence of Molecular Rearrangements303

7.9 Synthesis of Alkynes by Elimination Reactions307

7.10 The Acidity of Terminal Alkynes308

7.11 Replacement of the Acetylenic Hydrogen Atom of Terminal Alkynes309

7.12 Hydrogenation of Alkenes310

The Chemistry of...Mydrogenation in the Food Industry311

7.13 Hydrogenation：The Function of the Catalyst312

The Chemistry of…Homogeneous Asymmetric Catalytic Hydrogenation：Examples Involvlng L-DOPA,（S）-Naproxen,and Aspartame313

7.14 Hydrogenation of Alkynes315

7.15 Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency317

Chapter 8 Alkenes and AlkynesⅡ：Addition Reactions328

The Sea：A Treasury of Biologically Active Natural Products（Molecular graphic：Dactylyne，a halogenated marine natural product）328

8.1 Introduction：Addition to Alkenes329

8.2 Addition of Hydrogen Halides to Alkenes：Markovnikov’s Rule331

8.3 Stereochemistry of the Ionic Addition to an Alkene336

8.4 Addition of Sulfuric Acid to Alkenes337

8.5 Addition of Water to Alkenes：Acid-Catalyzed Hydration338

8.6 Alcohols from Alkenes through Oxymercuration-Demercuration：Markovnikov Addition340

8.7 Alcohols from Alkenes through Hydroboration-Oxidation：Anti-Markovnikov Syn Hydration343

8.8 Hydroboration：Synthesis of Alkylboranes343

8.9 Oxidation and Hydrolysis of Alkyboranes346

8.10 Summary of Alkene Hydration Methods348

8.11 Protonolysis of Alkyboranes348

8.12 Addition of Bromine and Chlorine to Alkenes349

8.13 Stereochemistry of the Addition of Halogens to Alkenes351

8.14 Halohydrin Formation354

The Chemistry of…Regiospecificity in Unsymmetrically Substituted Bromonium lons：Bromonium lons of Ethene,Propene,and2-Methlypropene355

8.15 Divalent Carbon Compounds：Carbenes357

8.16 Oxidations of Alkenes：Syn1，2-Dihydroxylation359

The Chemistry of…Catalytic Asymmetric Dihydroxylation361

8.17 Oxidative Cleavage of Alkenes362

8.18 Addition of Bromine and Chlorine to Alkynes365

8.19 Addition of Hydrogen Halides to Alkynes366

8.20 Oxidative Cleavage of Alkynes367

8.21 Synthetic Strategies Revisited367

The Chemistry 0f…Cholesterol Biosynthesis：Elegant and Familiar Reactions in Nature370

Chapter 9 Nuclear Magnetic Resonance and Mass Spectrometry：Tools for Structure Determination383

A Thermos？of Liquid Helium383（Molecular graphic：1-Chloro-2-propanol）383

9.1 Introduction384

9.2 The Electromagnetic Spectrum384

9.3 Nuclear Magnetic Resonance Spectroscopy386

9.4 Nuclear Spin： The Origin of the Signal390

9.5 Shielding and Deshielding of Protons392

9.6 The Chemical Shift394

9.7 Chemical Shift Equivalent and Nonequivalent Protons395

9.8 Signal Splitting： Spin-Spin Coupling397

9.9 Proton NMR Spectra and Rate Processes406

9.10 Carbon-l3 NMR Spectroscopy409

9.11 Two-Dimensional（2D）NMR Techniques414

The Chemistry of...Magnetic Resonance Imaging In Medicine417

9.12 An Introduction to Mass Spectrometry418

9.13 The Mass Spectrometer418

9.14 The Mass Spectrum421

9.15 Determination of Molecular Formulas and Molecular Weights423

9.16 Fragmentation428

9.17 GC/MS Analysis434

9.18 Mass Spectrometry of Biomolecules435

Chapter 10 Radical Reactions447

Calicheamicin γ1:A Radical Device for Slicing the Backbone of DNA447（Molecular graphic：Calicheamicin γ1Ⅰ，a molecule capable of double-strand DNA cleavage，bound to DNA）447

10.1 Introduction449

The Chemistry of...Radicals ln Biology,Medicine,and lndustry450

10.2 Homolytic Bond Dissociation Energies450

10.3 The Reactions of Alkanes with Halogens454

10.4 Chlorination of Methane：Mechanism of Reaction456

10.5 Chlorination of Methane：Energy Changes459

10.6 Halogenation of Higher Alkanes466

10.7 The Geometry of Alkyl Radicals469

10.8 Reactions that Generate Tetrahedral Stereogenic Carbons469

10.9 Radical Addition to Alkenes：The Anti-Markovnikov Addition of Hydrogen Bromide472

10.10 Radical Polymerization of Alkenes：Chain-Growth Polymers474

10.11 Other Important Radical Reactions476

Special Topic A：Chain-Growth Polymers485

Chapter 11 Alcohols and Ethers492

Molecular Hosts（Molecular graphic：Monensin sodium salt，an antibiotic that transports ions across cell membranes）492

11.1 Structure and Nomenclature493

11.2 Physical Properties of Alcohols and Ethers495

11.3 Important Alcohols and Ethers497

11.4 Synthesis of Alcohols from Alkenes499

11.5 Reactions of Alcohols501

11.6 Alcohols as Acids502

11.7 Conversion of Alcohols into Alkyl Halides503

11.8 Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides503

11.9 Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCl506

11.10 Tosylates，Mesylates，and Triflates：Leaving Group Derivatives of Alcohols507

The Chemistry of&Alkyl Phosphates510

11.11 Synthesis of Ethers510

11.12 Reactions of Ethers515

11.13 Epoxides516

The Chemistry of…The sharpless Asymmetric Epoxidation517

11.14 Reactions of Epoxides519

The Chemistry of…Epoxides,Carcinogens,and Biological Oxidation521

11.15 Anti1，2-Dihydroxylation of Alkenes via Epoxides523

The Chemistry of…Environmentally Friendly Alkene Oxidatlon Methods525

11.16 Crown Ethers：Nucleophilic Substitution Reactions in Relatively Nonpolar Aprotic Solvents by Phase-Transfer Catalysis526

11.17 Summary of Reactions of Alkenes，Alcohols，and Ethers529

Chapter 12 Alcohols from Carbonyl Compounds. Oxidation-Reduction and Orgganometallic Compounds537

The Two Aspects of the Coenzyme NADH（Molecular graphic：Nicotinamide [niacin]）537

12.1 Introduction538

12.2 Oxidation-Reduction Reactions in Organic Chemistry539

12.3 Alcohols by Reduction of Carbonyl Compounds541

The Chemistry of…Alcohol Dehydragenase544

The Chemistry of…Stereoselective Reductions of Carbonyl Groups544

12.4 Oxidation of Alcohols546

12.5 Organometallic Compounds550

12.6 Preparation of Organolithium and Organomagnesium Compounds551

12.7 Reactions of Organolithium and Organomagnesium Compounds553

12.8 Alcohols from Grignard Reagents556

12.9 Lithium Dialkylcuprates：The Corey-Posner，Whitesides-House Synthesis564

12.10 Protecting Groups566

First Review Problem Set573

Chapter 13 Conjugated Unsaturated Systems577

MoleCuies with the Nobel Prize in Theirsynthetic Lineage（Molecular graphic：Morphine，the synthesis of which involved the Diels-Alder reaction）577

13.1 Introduction578

13.2 Allylic Substitution and the Allyl Radical578

13.3 The Stability of the Allyl Radical582

13.4 The Allyl Cation586

13.5 Summary of Rules for Resonance587

13.6 Alkadienes and Polyunsaturated Hydrocarbons591

13.7 1，3-Butadiene：Electron Delocalization593

13.8 The Stability of Conjugated Dienes595

13.9 Ultraviolet-Visible Spectroscopy596

The Chemistry of…The Photochemistry of vision600

13.10 Electrophilic Attack on Conjugated Dienes：1，4Addition604

13.11 The Diels-Alder Reaction：A1，4-Cycloaddition Reaction of Dienes607

Chapter 14 Aromatic Compounds622

Geen Chemistry（Molecular graphic：Benzene，parent molecule in the family of aromatic hydrocarbons）622

14.1 Introduction623

14.2 Nomenclature of Benzene Derivatives624

14.3 Reactions of Benzene626

14.4 The Kekule Structure for Benzene627

14.5 The Stability of Benzene628

14.6 Modern Theories of the Structure of Benzene629

14.7 Hiickel’s Rule： The 4n+2πElectron Rule632

14.8 Other Aromatic Compounds640

The Chemistry of…Nanotubes643

14.9 Heterocylic Aromatic Compounds644

14.10 Aromatic Compounds in Biochemistry645

14.11 Spectroscopy of Aromatic Compounds648

The Chemistry of…Sunscreens（Catching the Sun’s Rays and what Happens to Them）652

Chapter 15 Reactions of Aromatic Compounds664

Biosynthesis of Thyroxine：Aromatic Substitution lnvolving Iodine（Molecular graphic：Thyroxine，an aromatic iodine-containing hormone associated with regulation of metabolic rate）664

15.1 Electrophilic Aromatic Substitution Reactions665

15.2 A General Mechanism for Electrophilic Aromatic Substitution：Arenium Ions666

15.3 Halogenation of Benzene668

15.4 Nitration of Benzene669

15.5 Sulfonation of Benzene670

15.6 Friedel-Crafts Alkylation671

15.7 Friedel-Crafts Acylation673

15.8 Limitations of Friedel-Crafts Reactions675

15.9 Synthetic Applications of Friedel-Crafts Acylations：The Clemmensen Reduction677

15.10 Effect of Substituents on Reactivity and Orientation679

15.11 Theory of Substituent Effects on Electrophilic Aromatic Substitution681

The Chemistry of…Iodine lncorporatlon In Thyroxine Biosynthesis681

15.12 Reactions of the Side Chain of Alkylbenzenes693

The Chemistry of…Industrial Styrene synthesis694

15.13 Alkenylbenzenes697

15.14 Synthetic Applications699

15.15 Allylic and Benzylic Halides in Nucleophilic Substitution Reactions703

15.16 Reduction of Aromatic Compounds705

Chapter 16 Aldehydes and KetonesI.Nucleophilic Addition to the Carbonyl Group716

A Very Versatile Vitamin,Pyridoxine（Vitamin B6）（Molecular graphic：Pyridoxal phosphate[vitamin B6]）716

16.1 Introduction717

16.2 Nomenclature of Aldehydes and Ketones717

16.3 Physical Properties719

16.4 Synthesis of Aldehydes720

16.5 Synthesis of Ketones724

16.6 Nucleophilic Addition to the Carbon-Oxygen Double Bond728

16.7 The Addition of Alcohols： Hemiacetals and Acetals731

16.8 The Addition of Primary and Secondary Amines738

The Chemistry of…Pyridoxal Phosphate741

16.9 The Addition of Hydrogen Cyanide743

16.10 The Addition of Ylides：The Wittig Reaction745

16.11 The Addition of Organometallic Reagents：The Reformatsky Reaction749

16.12 Oxidation of Aldehydes and Ketones751

16.13 Chemical Analyses for Aldehydes and Ketones753

16.14 Spectroscopic Properties of Aldehydes and Ketones754

Chaptet 17 Aldehydes and KetonesⅡ.Aldol Reactions769

TIM（Triose Phosphate Isomerase）Recycles Carbon via an Enol（Molecular graphic：Glyceraldehyde-3-phosphate， a key intermediate in metabolic energy production）769

17.1 The Acidity of the α Hydrogens of Carbonyl Compounds：Enolate Anions770

17.2 Keto and Enol Tautomers772

17.3 Reactions Via Enols and Enolate Anions773

17.4 The Aldol Reaction：The Addition of Enolate Anions to Aldehydes and Ketones779

The Chemistry of…A Retro-Aldol Reaction In Glycolysls—Dividing Assets to Double the ATP yield782

17.5 Crossed Aldol Reactions784

17.6 Cyclizations via Aldol Condensations789

17.7 Lithium Enolates791

The Chemistry of…Silyl Fnol Ethers795

17.8 α-Selenation：A Synthesis of α，β-Unsaturated Carbonyl Compounds796

17.9 Additions to α，β3-Unsaturated Carbonyl Compounds797

The Chemistry of…Calicheamicin γ1ⅠActivation for Cleavage of DNA801

Chapter 18 Carboxylic Acids and Their Derivatives.Nucleophilic Addition-Elimination at the Acyl Carbon813

A Common Bond（Molecular graphic：A portion of nylon 6，6，a polyamide）813

18.1 Introduction814

18.2 Nomenclature and Physical Properties814

18.3 Preparation of Carboxylic Acids823

18.4 Nucleophilic Addition-Elimination at the Acyl Carbon826

18.5 Acyl Chlorides828

18.6 Carboxylic Acid Anhydrides830

18.7 Esters832

18.8 Amides838

The Chemistry of…Penicillins845

18.9 Derivatives of Carbonic Acid846

18.10 Decarboxylation of Carboxylic Acids848

The Chemistry of…Thiamine849

18.11 Chemical Tests for Acyl Compounds851

Special TopicB：Step-Growth Polymers867

Chapter 19 Synthesis and Reactions of β-Dicarbonyl Compounds：More Chemistry of Enolate Ions878

Imposters（Molecular graphic：5-Fluorouracil， an enzyme inhibitor that has anticancer activity by masquerading as a natural substrate）878

19.1 Introduction879

19.2 The Claisen Condensation：The Synthesis of β-Keto Esters880

19.3 The Acetoacetic Ester Synthesis： Synthesis of Methyl Ketones（Substituted Acetones）885

19.4 The Malonic Ester Synthesis： Synthesis of Substituted Acetic Acids891

19.5 Further Reactions of Active Hydrogen Compounds895

19.6 Direct Alkylation of Esters and Nitriles896

19.7 Alkylation of 1，3-Dithianes897

19.8 The Knoevenagel Condensation898

19.9 Michael Additions898

19.10 The Mannich Reaction900

The Chenmistry of…A suicide Enzyme substrate901

19.11 Synthesis of Enamines：Stork Enamine Reactions902

The Chemistry of…Antibody-Catalyzed Aldol Condensations906

19.12 Barbiturates907

Special Topic C：Thiols，Sulfur Ylides，and Disulfides922

Special Topic D：Thiol Esters and Lipid Biosynthesis927

Chapter 20 Amines940

Neurotoxins and Neurotransmitters（Molecular graphic：Histrionicatoxin，a paralyzing neurotoxin from certain dart frogs）940

20.1 Nomenclature941

20.2 Physical Properties and Structure of Amines943

20.3 Basicity of Amines：Amine Salts945

The Chemistry of…HPLC Resolution of Enantiomers951

20.4 Some Biologically Important Amines952

20.5 Preparation of Amines954

20.6 Reactions of Amines962

20.7 Reactions of Amines with Nitrous Acid963

The Chemistry of…N-Nitrosoamines965

20.8 Replacement Reactions of Arenediazonium Salts966

20.9 Coupling Reactions of Arenediazonium Salts969

20.10 Reactions of Amines with Sulfonyl Chlorides972

20.11 The Sulfa Drugs： Sulfanilamide974

20.12 Analysis of Amines977

20.13 Eliminations Involving Ammonium Compounds979

Special TopicE：Alkaloids994

Chapter 21 Phenols and Aryl Halides：Nucleophilic Aromatic Substitution1000

A Silver Chalice（Molecular graphic：4-tert-Butylcalix[4]arene， a chalice-shaped molecule）1001

21.1 Structure and Nomenclature of Phenols1001

21.2 Naturally Occurring Phenols1002

21.3 Physical Properties of Phenols1003

21.4 Synthesis of Phenols1003

The Chemistry of…Polyketide Anticancer Antiblotic Biosynthesis1004

21.5 Reactions of Phenols as Acids1008

21.6 Other Reactions of the O—H Group of Phenols1010

21.7 Cleavage of Alkyl Aryl Ethers1011

21.8 Reactions of the Benzene Ring of Phenols1012

21.9 The Claisen Rearrangement1014

21.10 Quinones1015

21.11 Aryl Halides and Nucleophilic Aromatic Substitution1016

The Chemistry of…The Bombardier Beetles’s Noxious spray1017

The Chemistry of…Bacterlal Dehalogenatlon of a PCB Derivative1020

21.12 Spectroscopic Analysis of Phenols and Aryl Halides1025

Second Review：Problem Set1035

Special Topic F：Electrocyclic and Cycloaddition Reactions1041

Special Topic G：Transition Metal Organometallic Compounds1055

Special Topic H：Organic Halides and Organometallic Compounds In the Environment1066

Chapter 22 Carbohydrates1072

Carhohydrate ReCOgnition in Healing and Disease（Molelcular graphic：Sialyl Lewis，x a carbohydrate that is important in the recognition and healing of traumatized tissue）1072

22.1 Introduction1073

22.2 Monosaccharides1076

22.3 Mutarotation1081

22.4 Glycoside Formation1082

22.5 Other Reactions of Monosaccharides1085

22.6 Oxidation Reactions of Monosaccharides1088

22.7 Reduction of Monosaccharides：Alditols1093

22.8 Reactions of Monosaccharides with Phenylhydrazine：Osazones1094

22.9 Synthesis and Degradation of Monosaccharides1095

22.10 The D Family of Aldoses1097

22.11 Fischer’s Proof of the Configuration of D-（+）-Glucose1099

The Chemistry of…Stereoselective synthesis of All the L-Aldohexoses1101

22.12 Disaccharides1102

The Chemistry of…Artificial Sweeteners（How sweet it is）1106

22.13 Polysaccharides1107

The Chemistry of…Oligosaccharldes synthesis on a Solid Support-The Glycal Assembly Approach1112

22.14 Other Biologically Important Sugars1113

22.15 Sugars that Contain Nitrogen1114

22.16 Glycolipids and Glycoproteins of the Cell Surface：Cell Recognition and the Immune System1116

The Chemistry of…Vacclnes Agalnst CanCer1118

22.17 Carbohydrate Antibiotics1119

Chapter 23 Lipids1129

lnsulation for Nerves（Molecular graphic：A sphingomyelin molecule，found in myelin sheath membranes）1129

23.1 Introduction1130

23.2 Fatty Acids and Triacylglycerols1131

The Chemistry of…Olestra and Other Fat Substitutes1135

Thhe Chemistry of…Self-Assembled Monolayers—Lipids in Materials SCienCe and Bioengineering1138

23.3 Terpenes and Terpenoids1139

23.4 Steroids1143

23.5 Prostaglandins1153

23.6 Phospholipids and Cell Membranes1154

The Chemistry of…Stealth? Lipesomes for Drug Delivery1157

23.7 Waxes1158

Chapter 24 Amino Acids and Proteins1166

Catalytic Antibodies：Designer Catalysts（Molecular graphic：A synthetic Diels-Alderase catalytic antibody with a bound hapten）1166

24.1 Introduction1167

24.2 Amnino Acids1168

24.3 Synthesis of α-Amino Acids1173

24.4 Polypeptides and Proteins1177

24.5 Primary Structure of Polypeptides and Proteins1181

24.6 Examples of Polypeptide and Protein Primary Structure1185

The Chemistry of…Sickle-Cell Anemia1188

24.7 Polypeptide and Protein Synthesis1189

24.8 Secondary，Tertiary， and Quaternary Structure of Proteins1195

24.9 Introduction to Enzymes1200

24.10 Lysozyme：Mode of Action of an Enzyme1202

24.11 Serine Proteases1203

The Chemistry of…Some CatalytiC Antibodies1208

24.12 Hemoglobin：A Conjugated Protein1210

24.13 Purification and Analysis of Polypeptides and Proteins1211

24.14 Proteomics1213

Chapter 25 NUCleic Acids and Protein Synthesis1220

Tools for Finding Families（Molecular graphic：A cytosine-guanine base pair， depicting the van der Waals surface as an electrostatic potential map）1220

25.1 Introduction1221

25.2 Nucleotides and Nucleosides1222

25.3 Laboratory Synthesis of Nucleosides and Nucleotides1225

25.4 Deoxyribonucleic Acid：DNA1228

25.5 RNA and Protein Synthesis1236

25.6 Determining the Base Sequence of DNA：The Chain Terminating （Dideoxynucleotide Method）1243

25.7 Laboratory Syntesis of Oligonucleotides1247

25.8 The Polymerase Chain Reaction1249

25.9 Sequencing of the Human Genome：An Instruction Book for the Molecules of Life1251