Organic Chemistry

Note: Supplemental materials are not guaranteed with Rental or Used book purchases.

ISBN: 9780131478718 | 0131478710
Cover: Hardcover
Copyright: 1/1/2006

Rent

(Recommended)

$61.80

Term

Due

Price

Semester

Aug 2

$68.67

Quarter

Jul 18

$65.24

Short Term

Jun 7

$61.80

*This item is part of an exclusive publisher rental program and requires an additional convenience fee. This fee will be reflected in the shopping cart.
Buy Used

In Stock Usually Ships in 24 Hours.

$94.30

In a highly accessible fashion, this top-selling book bridges the gap between conceptual understanding and actual applicationwhile strongly emphasizing the development of problem-solving skills. The book focuses on traditional organic chemistry topics and offers up-to-date aspects of spectroscopy, relevant photographs, and many applications to polymer chemistry integrated throughout the book.

Preface

xxiii

About the Author

xli

1 Introduction and Review

(38)

1-1 The Origins of Organic Chemistry

(2)

1-2 Principles of Atomic Structure

(3)

1-3 Bond Formation: The Octet Rule

(1)

1-4 Lewis Structures

(1)

1-5 Multiple Bonding

(1)

Summary: Common Bonding Patterns (Uncharged)

(1)

1-6 Electronegativity and Bond Polarity

(2)

1-7 Formal Charges

(1)

1-8 Ionic Structures

(1)

Summary: Common Bonding Patterns in Organic Compounds and Ions

(1)

1-9 Resonance

(4)

1-10 Structural Formulas

(3)

1-11 Molecular Formulas and Empirical Formulas

(1)

1-12 Arrhenius Acids and Bases

(1)

1-13 Bransted-Lowry Acids and Bases

(7)

1-14 Lewis Acids and Bases

(3)

Chapter 1 Glossary

(2)

Study Problems

(5)

2 Structure and Properties of Organic Molecules

(42)

2-1 Wave Properties of Electrons in Orbitals

(2)

2-2 Molecular Orbitals

(3)

2-3 Pi Bonding

(1)

2-4 Hybridization and Molecular Shapes

(4)

2-5 Drawing Three-Dimensional Molecules

(1)

2-6 General Rules of Hybridization and Geometry

(4)

2-7 Bond Rotation

(2)

2-8 Isomerism

(2)

2-9 Polarity of Bonds and Molecules

(3)

2-10 Intermolecular Forces

(4)

2-11 Polarity Effects on Solubilities

(3)

2-12 Hydrocarbons

(3)

2-13 Organic Compounds Containing Oxygen

(2)

2-14 Organic Compounds Containing Nitrogen

(2)

Chapter 2 Glossary

(2)

Study Problems

(4)

3 Structure and Stereochemistry of Alkanes

(44)

3-1 Classification of Hydrocarbons (Review)

(1)

3-2 Molecular Formulas of Alkanes

(1)

3-3 Nomenclature of Alkanes

(6)

Summary: Rules for Naming Alkanes

(1)

3-4 Physical Properties of Alkanes

(2)

3-5 Uses and Sources of Alkanes

(2)

3-6 Reactions of Alkanes

(1)

3-7 Structure and Conformations of Alkanes

(4)

3-8 Conformations of Butane

(2)

3-9 Conformations of Higher Alkanes

100

(1)

3-10 Cycloalkanes

100

(3)

3-11 cis-trans Isomerism in Cycloalkanes

103

(1)

3-12 Stabilities of Cycloalkanes; Ring Strain

103

(4)

3-13 Cyclohexane Conformations

107

(4)

3-14 Conformations of Monosubstituted Cyclohexanes

111

(3)

3-15 Conformations of Disubstituted Cyclohexanes

114

(3)

3-16 Bicyclic Molecules

117

(2)

Chapter 3 Glossary

119

(3)

Study Problems

122

(3)

4 The Study of Chemical Reactions

125

(42)

4-1 Introduction

125

(1)

4-2 Chlorination of Methane

125

(1)

4-3 The Free-Radical Chain Reaction

126

(4)

Key Mechanism: Free-Radical Halogenation

128

(2)

4-4 Equilibrium Constants and Free Energy

130

(3)

4-5 Enthalpy and Entropy

133

(1)

4-6 Bond-Dissociation Enthalpies

134

(1)

4-7 Enthalpy Changes in Chlorination

135

(2)

4-8 Kinetics and the Rate Equation

137

(2)

4-9 Activation Energy and the Temperature Dependence of Rates

139

(1)

4-10 Transition States

140

(2)

4-11 Rates of Multistep Reactions

142

(1)

4-12 Temperature Dependence of Halogenation

143

(1)

4-13 Selectivity in Halogenation

144

(5)

4-14 The Hammond Postulate

149

(4)

4-15 Radical Inhibitors

153

(2)

4-16 Reactive Intermediates

155

(5)

Summary: Reactive Intermediates

160

(1)

Chapter 4 Glossary

160

(3)

Study Problems

163

(4)

5 Stereochemistry

167

(45)

5-1 Introduction

167

(1)

5-2 Chirality

168

(6)

5-3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms

174

(5)

5-4 Optical Activity

179

(5)

5-5 Biological Discrimination of Enantiomers

184

(1)

5-6 Racemic Mixtures

185

(1)

5-7 Enantiomeric Excess and Optical Purity

186

(1)

5-8 Chirality of Conformationally Mobile Systems

187

(2)

5-9 Chiral Compounds without Asymmetric Atoms

189

(2)

5-10 Fischer Projections

191

(5)

Summary: Fischer Projections and Their Use

196

(1)

5-11 Diastereomers

196

(2)

Summary: Types of Isomers

197

(1)

5-12 Stereochemistry of Molecules with Two or More Asymmetric Carbons

198

(1)

5-13 Meso Compounds

199

(2)

5-14 Absolute and Relative Configuration

201

(2)

5-15 Physical Properties of Diastereomers

203

(1)

5-16 Resolution of Enantiomers

204

(3)

Chapter 5 Glossary

207

(2)

Study Problems

209

(3)

6 Alkyl Halides: Nucleophilic Substitution and Elimination

212

(67)

6-1 Introduction

212

(1)

6-2 Nomenclature of Alkyl Halides

213

(2)

6-3 Common Uses of Alkyl Halides

215

(2)

6-4 Structure of Alkyl Halides

217

(1)

6-5 Physical Properties of Alkyl Halides

218

(2)

6-6 Preparation of Alkyl Halides

220

(5)

Summary: Methods for Preparing Alkyl Halides

223

(2)

6-7 Reactions of Alkyl Halides: Substitution and Elimination

225

(1)

6-8 Second-Order Nucleophilic Substitution: The SN2 Reaction

226

(2)

Key Mechanism: The SN2 Reaction

227

(1)

6-9 Generality of the SN2 Reaction

228

(2)

Summary: SN2 Reactions of Alkyl Halides

228

(2)

6-10 Factors Affecting SN2 Reactions: Strength of the Nucleophile

230

(4)

Summary: Trends in Nucleophilicity

231

(3)

6-11 Reactivity of the Substrate in SN2 Reactions

234

(4)

6-12 Stereochemistry of the SN2 Reaction

238

(2)

6-13 First-Order Nucleophilic Substitution: The SN1 Reaction

240

(4)

Key Mechanism: The 5N1 Reaction

241

(3)

6-14 Stereochemistry of the SN1 Reaction

244

(2)

6-15 Rearrangements in SN I Reactions

246

(3)

6-16 Comparison of SN1 and SN2 Reactions

249

(3)

Summary: Nucleophilic Substitutions

251

(1)

6-17 First-Order Elimination: The El Reaction

252

(5)

Key Mechanism: The El Reaction

252

(4)

Summary: Carbocation Reactions

256

(1)

6-18 Positional Orientation of Elimination: Zaitsev's Rule

257

(1)

6-19 Second-Order Elimination: The E2 Reaction

258

(3)

Key Mechanism: The E2 Reaction

259

(2)

6-20 Stereochemistry of the E2 Reaction

261

(1)

6-21 Comparison of El and E2 Elimination Mechanisms

262

(8)

Summary: Elimination Reactions

264

(3)

Summary: Reactions of Alkyl Halides

267

(3)

Chapter 6 Glossary

270

(3)

Study Problems

273

(6)

7 Structure and Synthesis of Alkenes

279

(42)

7-1 Introduction

279

(1)

7-2 The Orbital Description of the Alkene Double Bond

280

(1)

7-3 Elements of Unsaturation

281

(2)

7-4 Nomenclature of Alkenes

283

(2)

7-5 Nomenclature of Cis-Trans Isomers

285

(3)

Summary: Rules for Naming Alkenes

287

(1)

7-6 Commercial Importance of Alkenes

288

(2)

7-7 Stability of Alkenes

290

(6)

7-8 Physical Properties of Alkenes

296

(2)

7-9 Alkene Synthesis by Elimination of Alkyl Halides

298

(8)

7-10 Alkene Synthesis by Dehydration of Alcohols

306

(3)

Key Mechanism: Acid-Catalyzed Dehydration of an Alcohol

307

(2)

7-11 Alkene Synthesis by High-Temperature Industrial Methods

309

(7)

Summary: Methods for Synthesis of Alkenes

314

(2)

Chapter 7 Glossary

316

(2)

Study Problems

318

(3)

8 Reactions of Alkenes

321

(61)

8-1 Reactivity of the Carbon-Carbon Double Bond

321

(1)

8-2 Electrophilic Addition to Alkenes

322

(2)

Key Mechanism: Electrophilic Addition to Alkenes

322

(2)

8-3 Addition of Hydrogen Halides to Alkenes

324

(6)

8-4 Addition of Water: Hydration of Alkenes

330

(3)

8-5 Hydration by Oxymercuration-Demercuration

333

(2)

8-6 Alkoxymercuration-Demercuration

335

(1)

8-7 Hydroboration of Alkenes

336

(6)

8-8 Addition of Halogens to Alkenes

342

(3)

8-9 Formation of Halohydrins

345

(3)

8-10 Catalytic Hydrogenation of Alkenes

348

(2)

8-11 Addition of Carbenes to Alkenes

350

(3)

8-12 Epoxidation of Alkenes

353

(2)

8-13 Acid-Catalyzed Opening of Epoxides

355

(3)

8-14 Syn Hydroxylation of Alkenes

358

(2)

8-15 Oxidative Cleavage of Alkenes

360

(3)

8-16 Polymerization of Alkenes

363

(11)

Summary: Reactions of Alkenes

370

(4)

Chapter 8 Glossary

374

(2)

Study Problems

376

(6)

9 Alkynes

382

(35)

9-1 Introduction

382

(1)

9-2 Nomenclature of Alkynes

383

(1)

9-3 Physical Properties of Alkynes

384

(1)

9-4 Commercial Importance of Alkynes

384

(2)

9-5 Electronic Structure of Alkynes

386

(1)

9-6 Acidity of Alkynes; Formation of Acetylide Ions

387

(2)

9-7 Synthesis of Alkynes from Acetylides

389

(4)

9-8 Synthesis of Alkynes by Elimination Reactions

393

(3)

Summary: Syntheses of Alkynes

396

(1)

9-9 Addition Reactions of Alkynes

396

(10)

9-10 Oxidation of Alkynes

406

(6)

Summary: Reactions of Alkynes

409

(3)

Chapter 9 Glossary

412

(1)

Study Problems

413

(4)

10 Structure and Synthesis of Alcohols

417

(43)

10-1 Introduction

417

(1)

10-2 Structure and Classification of Alcohols

417

(2)

10-3 Nomenclature of Alcohols and Phenols

419

(4)

10-4 Physical Properties of Alcohols

423

(2)

10-5 Commercially Important Alcohols

425

(2)

10-6 Acidity of Alcohols and Phenols

427

(3)

10-7 Synthesis of Alcohols: Introduction and Review

430

(2)

Summary: Previous Alcohol Syntheses

430

(2)

10-8 Organometallic Reagents for Alcohol Synthesis

432

(3)

10-9 Addition of Organometallic Reagents to Carbonyl Compounds

435

(8)

Key Mechanism: Grignard Reactions

435

(7)

Summary: Grignard Reactions

442

(1)

10-10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides

443

(2)

10-11 Reduction of the Carbonyl Group: Synthesis of 1° and 2° Alcohols

445

(6)

Summary: Reactions of LiAlH4 and NaBH4

448

(1)

Summary: Alcohol Syntheses

449

(2)

10-12 Thiols (Mercaptans)

451

(3)

Chapter 10 Glossary

454

(1)

Study Problems

455

(5)

11 Reactions of Alcohols

460

(48)

11-1 Oxidation States of Alcohols and Related Functional Groups

460

(2)

11-2 Oxidation of Alcohols

462

(3)

11-3 Additional Methods for Oxidizing Alcohols

465

(2)

11-4 Biological Oxidation of Alcohols

467

(2)

11-5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates

469

(3)

Summary: SN2 Reactions of Tosylate Esters

471

(1)

11-6 Reduction of Alcohols

472

(1)

11-7 Reactions of Alcohols with Hydrohalic Acids

472

(5)

11-8 Reactions of Alcohols with Phosphorus Halides

477

(1)

11-9 Reactions of Alcohols with Thionyl Chloride

478

(2)

11-10 Dehydration Reactions of Alcohols

480

(8)

11-11 Unique Reactions of Diols

488

(2)

11-12 Esterification of Alcohols

490

(1)

11-13 Esters of Inorganic Acids

491

(3)

11-14 Reactions of Alkoxides

494

(8)

Key Mechanism: The Williamson Ether Synthesis

494

(5)

Summary: Reactions of Alcohols

499

(3)

Chapter 11 Glossary

502

(1)

Study Problems

503

(5)

12 Infrared Spectroscopy and Mass Spectrometry

508

(51)

12-1 Introduction

508

(1)

12-2 The Electromagnetic Spectrum

509

(1)

12-3 The Infrared Region

510

12-4 Molecular Vibrations 51

(512)

12-5 1R-Active and IR-Inactive Vibrations

513

(1)

12-6 Measurement of the IR Spectrum

514

(3)

12-7 Infrared Spectroscopy of Hydrocarbons

517

(5)

12-8 Characteristic Absorptions of Alcohols and Amines

522

(1)

12-9 Characteristic Absorptions of Carbonyl Compounds

523

(6)

12-10 Characteristic Absorptions of C-N Bonds

529

(1)

12-11 Simplified Summary of IR Stretching Frequencies

530

(2)

12-12 Reading and Interpreting IR Spectra (Solved Problems)

532

(5)

12-13 Introduction to Mass Spectrometry

537

(4)

12-14 Determination of the Molecular Formula by Mass Spectrometry

541

(3)

12-15 Fragmentation Patterns in Mass Spectrometry

544

(7)

Summary: Common Fragmentation Patterns

549

(2)

Chapter 12 Glossary

551

(1)

Study Problems

552

(7)

13 Nuclear Magnetic Resonance Spectroscopy

559

(64)

13-1 Introduction

559

(1)

13-2 Theory of Nuclear Magnetic Resonance

559

(3)

13-3 Magnetic Shielding by Electrons

562

(2)

13-4 The NMR Spectrometer

564

(1)

13-5 The Chemical Shift

565

(7)

13-6 The Number of Signals

572

(1)

13-7 Areas of the Peaks

573

(3)

13-8 Spin-Spin Splitting

576

(9)

13-9 Complex Splitting

585

(3)

13-10 Stereochemical Nonequivalence of Protons

588

(3)

13-11 Time Dependence of NMR Spectroscopy

591

(8)

Problem-Solving Strategy: Interpreting Proton NMR Spectra

594

(5)

13-12 Carbon-13 NMR Spectroscopy

599

(8)

13-13 Interpreting Carbon NMR Spectra

607

(2)

13-14 Nuclear Magnetic Resonance Imaging

609

(5)

Problem-Solving Strategy: Spectroscopy Problems

610

(4)

Chapter 13 Glossary

614

(2)

Study Problems

616

(7)

14 Ethers, Epoxides, and Sulfides

623

(40)

14-1 Introduction

623

(1)

14-2 Physical Properties of Ethers

623

(5)

14-3 Nomenclature of Ethers

628

(3)

14-4 Spectroscopy of Ethers

631

(2)

14-5 The Williamson Ether Synthesis

633

(1)

14-6 Synthesis of Ethers by Alkoxymercuration-Demercuration

634

(1)

14-7 Industrial Synthesis: Bimolecular Dehydration of Alcohols

635

(1)

Summary: Syntheses of Ethers

636

(1)

14-8 Cleavage of Ethers by HBr and HI

636

(3)

14-9 Autoxidation of Ethers

639

(1)

Summary: Reactions of Ethers

639

(1)

14-10 Sulfides (Thioethers)

640

(2)

14-11 Synthesis of Epoxides

642

(3)

Summary: Epoxide Syntheses

645

(1)

14-12 Acid-Catalyzed Ring Opening of Epoxides

645

(4)

14-13 Base-Catalyzed Ring Opening of Epoxides

649

(1)

14-14 Orientation of Epoxide Ring Opening

650

(2)

14-15 Reactions of Epoxides with Grignard and Organolithium Reagents

652

(1)

14-16 Epoxy Resins: The Advent of Modern Glues

653

(3)

Summary: Reactions of Epoxides

655

(1)

Chapter 14 Glossary

656

(2)

Study Problems

658

(5)

15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

663

(42)

15-1 Introduction

663

(1)

15-2 Stabilities of Dienes

663

(2)

15-3 Molecular Orbital Picture of a Conjugated System

665

(4)

15-4 Allylic Cations

669

(1)

15-5 1,2- and 1,4-Addition to Conjugated Dienes

670

(2)

15-6 Kinetic versus Thermodynamic Control in the Addition of HBr to 1,3-Butadiene

672

(2)

15-7 Allylic Radicals

674

(2)

15-8 Molecular Orbitals of the Allylic System

676

(2)

15-9 Electronic Configurations of the Ally! Radical, Cation, and Anion

678

(1)

15-10 SN2 Displacement Reactions of Allylic Halides and Tosylates

679

(1)

15-11 The Diels-Alder Reaction

680

(9)

Key Mechanism: The Diels-Alder Reaction

680

(9)

15-12 The Diels-Alder as an Example of a Pericyclic Reaction

689

(3)

15-13 Ultraviolet Absorption Spectroscopy

692

(7)

Chapter 15 Glossary

699

(2)

Study Problems

701

(4)

16 Aromatic Compounds

705

(44)

16-1 Introduction: The Discovery of Benzene

705

(1)

16-2 The Structure and Properties of Benzene

705

(4)

16-3 The Molecular Orbitals of Benzene

709

(3)

16-4 The Molecular Orbital Picture of Cyclobutadiene

712

(2)

16-5 Aromatic, Antiaromatic, and Nonaromatic Compounds

714

(1)

16-6 Hackers Rule

714

(2)

16-7 Molecular Orbital Derivation of Hiickel's Rule

716

(1)

16-8 Aromatic Ions

717

(6)

16-9 Heterocyclic Aromatic Compounds

723

(4)

16-10 Polynuclear Aromatic Hydrocarbons

727

(2)

16-11 Aromatic Allotropes of Carbon

729

(2)

16-12 Fused Heterocyclic Compounds

731

(1)

16-13 Nomenclature of Benzene Derivatives

732

(2)

16-14 Physical Properties of Benzene and Its Derivatives

734

(1)

16-15 Spectroscopy of Aromatic Compounds

735

(3)

Chapter 16 Glossary

738

(2)

Study Problems

740

(9)

17 Reactions of Aromatic Compounds

749

(56)

17-1 Electrophilic Aromatic Substitution

749

(2)

Key Mechanism: Electrophilic Aromatic Substitution

750

(1)

17-2 Halogenation of Benzene

751

(2)

17-3 Nitration of Benzene

753

(2)

17-4 Sulfonation of Benzene

755

(2)

17-5 Nitration of Toluene: The Effect of Alkyl Substitution

757

(2)

17-6 Activating, Ortho, Para-Directing Substituents

759

(4)

Summary: Activating, Ortho, Para-Directors

762

(1)

17-7 Deactivating, Meta-Directing Substituents

763

(3)

Summary: Deactivating, Meta-Directors

766

(1)

17-8 Halogen Substituents: Deactivating, but Ortho, Para-Directing

766

(2)

Summary: Directing Effects of Substituents

768

(1)

17-9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution

768

(3)

17-10 The Friedel-Crafts Alkylation

771

(4)

17-11 The Friedel-Crafts Acylation

775

(5)

Summary: Comparison of Friedel-Crafts Alkylation and Acylation

778

(2)

17-12 Nucleophilic Aromatic Substitution

780

(5)

17-13 Addition Reactions of Benzene Derivatives

785

(2)

17-14 Side-Chain Reactions of Benzene Derivatives

787

(4)

17-15 Reactions of Phenols

791

(6)

Summary: Reactions of Aromatic Compounds

794

(3)

Chapter 17 Glossary

797

(3)

Study Problems

800

(5)

18 Ketones and Aldehydes

805

(65)

18-1 Carbonyl Compounds

805

(1)

18-2 Structure of the Carbonyl Group

806

(1)

18-3 Nomenclature of Ketones and Aldehydes

806

(3)

18-4 Physical Properties of Ketones and Aldehydes

809

(2)

18-5 Spectroscopy of Ketones and Aldehydes

811

(7)

18-6 Industrial Importance of Ketones and Aldehydes

818

(1)

18-7 Review of Syntheses of Ketones and Aldehydes

818

(4)

18-8 Synthesis of Ketones and Aldehydes Using 1,3-Dithianes

822

(1)

18-9 Synthesis of Ketones from Carboxylic Acids

823

(1)

18-10 Synthesis of Ketones from Nitriles

824

(1)

18-11 Synthesis of Aldehydes and Ketones from Acid Chlorides

825

(4)

Summary: Syntheses of Ketones and Aldehydes

826

(3)

18-12 Reactions of Ketones and Aldehydes: Nucleophilic Addition

829

(3)

Key Mechanism: Nucleophilic Additions to Carbonyl Groups

831

(1)

18-13 The Wittig Reaction

832

(4)

18-14 Hydration of Ketones and Aldehydes

836

(2)

18-15 Formation of Cyanohydrins

838

(2)

18-16 Formation of Imines

840

(3)

Key Mechanism: Formation of Imines

840

(3)

18-17 Condensations with Hydroxylamine and Hydrazines

843

(2)

Summary: Condensations of Amines with Ketones and Aldehydes

844

(1)

18-18 Formation of Acetals

845

(5)

Key Mechanism: Formation of Acetals

846

(2)

Problem-Solving Strategy: Proposing Reaction Mechanisms

848

(2)

18-19 Use of Acetals as Protecting Groups

850

(2)

18-20 Oxidation of Aldehydes

852

(1)

18-21 Reductions of Ketones and Aldehydes

853

(5)

Summary: Reactions of Ketones and Aldehydes

855

(3)

Glossary

858

(3)

Study Problems

861

(9)

19 Amines

870

(65)

19-1 Introduction

870

(1)

19-2 Nomenclature of Amines

871

(2)

19-3 Structure of Amines

873

(2)

19-4 Physical Properties of Amines

875

(2)

19-5 Basicity of Amines

877

(1)

19-6 Effects on Amine Basicity

878

(2)

19-7 Salts of Amines

880

(2)

19-8 Amine Salts as Phase-Transfer Catalysts

882

(2)

19-9 Spectroscopy of Amines

884

(4)

19-10 Reactions of Amines with Ketones and Aldehydes (Review)

888

(1)

19-11 Aromatic Substitution of Arylamines and Pyridine (Review)

888

(4)

19-12 Alkylation of Amines by Alkyl Halides

892

(1)

19-13 Acylation of Amines by Acid Chlorides

893

(2)

19-14 Formation of Sulfonamides

895

(2)

19-15 Amines as Leaving Groups: The Hofmann Elimination

897

(3)

19-16 Oxidation of Amines: The Cope Elimination

900

(2)

19-17 Reactions of Amines with Nitrous Acid

902

(2)

19-18 Reactions of Arenediazonium Salts

904

(7)

Summary: Reactions of Amines

908

(3)

19-19 Synthesis of Amines by Reductive Amination

911

(2)

19-20 Synthesis of Amines by Acylation-Reduction

913

(2)

19-21 Syntheses Limited to Primary Amines

915

(8)

Summary: Synthesis of Amines

921

(2)

Chapter 19 Glossary

923

(3)

Study Problems

926

(9)

20 Carboxylic Acids

935

(43)

20-1 Introduction

935

(1)

20-2 Nomenclature of Carboxylic Acids

935

(4)

20-3 Structure and Physical Properties of Carboxylic Acids

939

(1)

20-4 Acidity of Carboxylic Acids

940

(4)

20-5 Salts of Carboxylic Acids

944

(3)

20-6 Commercial Sources of Carboxylic Acids

947

(1)

20-7 Spectroscopy of Carboxylic Acids

948

(4)

20-8 Synthesis of Carboxylic Acids

952

(5)

Summary: Syntheses of Carboxylic Acids

955

(2)

20-9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution

957

(1)

20-10 Condensation of Acids with Alcohols: The Fischer Esterification

958

(4)

Key Mechanism: Fischer Esterification

959

(3)

20-11 Esterification Using Diazomethane

962

(1)

20-12 Condensation of Acids with Amines: Direct Synthesis of Amides

963

(1)

20-13 Reduction of Carboxylic Acids

963

(2)

20-14 Alkylation of Carboxylic Acids to Form Ketones

965

(1)

20-15 Synthesis and Use of Acid Chlorides

966

(4)

Summary: Reactions of Carboxylic Acids

968

(2)

Chapter 20 Glossary

970

(1)

Study Problems

971

(7)

21 Carboxylic Acid Derivatives

978

(63)

21-1 Introduction

978

(1)

21-2 Structure and Nomenclature of Acid Derivatives

979

(6)

21-3 Physical Properties of Carboxylic Acid Derivatives

985

(3)

21-4 Spectroscopy of Carboxylic Acid Derivatives

988

(6)

21-5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution

994

(9)

Key Mechanism: Addition-Elimination Mechanism of Nucleophilic Acyl Substitution

995

(8)

21-6 Transesterification

1003

(3)

21-7 Hydrolysis of Carboxylic Acid Derivatives

1006

(5)

21-8 Reduction of Acid Derivatives

1011

(2)

21-9 Reactions of Acid Derivatives with Organometallic Reagents

1013

(1)

21-10 Summary of the Chemistry of Acid Chlorides

1014

(2)

21-11 Summary of the Chemistry of Anhydrides

1016

(3)

21-12 Summary of the Chemistry of Esters

1019

(3)

21-13 Summary of the Chemistry of Amides

1022

(3)

21-14 Summary of the Chemistry of Nitriles

1025

(1)

21-15 Thioesters

1026

(2)

21-16 Esters and Amides of Carbonic Acid

1028

(2)

Chapter 21 Glossary

1030

(2)

Study Problems

1032

(9)

22 Condensations and Alpha Substitutions of Carbonyl Compounds

1041

(56)

22-1 Introduction

1041

(1)

22-2 Enols and Enolate Ions

1042

(4)

22-3 Alpha Halogenation of Ketones

1046

(5)

22-4 a Bromination of Acids: The HVZ Reaction

1051

(1)

22-5 Alkylation of Enolate Ions

1052

(1)

22-6 Formation and Alkylation of Enamines

1053

(3)

22-7 The Aldol Condensation of Ketones and Aldehydes

1056

(4)

Key Mechanism: Base-Catalyzed Aldol Condensation

1056

(4)

22-8 Dehydration of Aldol Products

1060

(1)

Key Mechanism: Base-Catalyzed Dehydration of an Aldol

1060

(1)

22-9 Crossed Aldol Condensations

1061

(3)

Problem-Solving Strategy: Proposing Reaction Mechanisms

1062

(2)

22-10 Aldol Cyclizations

1064

(1)

22-11 Planning Syntheses Using Aldol Condensations

1065

(2)

22-12 The Claisen Ester Condensation

1067

(3)

Key Mechanism: The Claisen Ester Condensation

1067

(3)

22-13 The Dieckmann Condensation: A Claisen Cyclization

1070

(1)

22-14 Crossed Claisen Condensations

1071

(3)

22-15 Syntheses Using /3-Dicarbonyl Compounds

1074

(2)

22-16 The Malonic Ester Synthesis

1076

(3)

22-17 The Acetoacetic Ester Synthesis

1079

(2)

22-18 Conjugate Additions: The Michael Reaction

1081

(4)

22-19 The Robinson Annulation

1085

(3)

Problem-Solving Strategy: Proposing Reaction

Mechanisms

1086

(2)

Summary: Enolate Additions and Condensations

1088

(2)

Chapter 22 Glossary

1090

(2)

Study Problems

1092

(5)

23 Carbohydrates and Nucleic Acids

1097

(56)

23-1 Introduction

1097

(1)

23-2 Classification of Carbohydrates

1098

(1)

23-3 Monosaccharides

1099

(3)

23-4 Erythro and Threo Diastereomers

1102

(1)

23-5 Epimers

1103

(1)

23-6 Cyclic Structures of Monosaccharides

1104

(4)

23-7 Anomers of Monosaccharides; Mutarotation

1108

(2)

23-8 Reactions of Monosaccharides: Side Reactions in Base

1110

(2)

23-9 Reduction of Monosaccharides

1112

(1)

23-10 Oxidation of Monosaccharides; Reducing Sugars

1113

(2)

23-11 Nonreducing Sugars: Formation of Glycosides

1115

(2)

23-12 Ether and Ester Formation

1117

(2)

23-13 Reactions with Phenylhydrazine: Osazone Formation

1119

(1)

23-14 Chain Shortening: The Ruff Degradation

1120

(1)

23-15 Chain Lengthening: The Kiliani-Fischer Synthesis

1121

(3)

Summary: Reactions of Sugars

1122

(2)

23-16 Fischer's Proof of the Configuration of Glucose

1124

(3)

23-17 Determination of Ring Size; Periodic Acid Cleavage of Sugars

1127

(2)

23-18 Disaccharides

1129

(5)

23-19 Polysaccharides

1134

(3)

23-20 Nucleic Acids: Introduction

1137

(2)

23-21 Ribonucleosides and Ribonucleotides

1139

(2)

23-22 The Structure of Ribonucleic Acid

1141

(1)

23-23 Deoxyribose and the Structure of Deoxyribonucleic Acid

1141

(4)

23-24 Additional Functions of Nucleotides

1145

(2)

Chapter 23 Glossary

1147

(2)

Study Problems

1149

(4)

24 Amino Acids, Peptides, and Proteins

1153

(47)

24-1 Introduction

1153

(1)

24-2 Structure and Stereochemistry of the a-Amino Acids

1154

(4)

24-3 Acid-Base Properties of Amino Acids

1158

(2)

24-4 Isoelectric Points and Electrophoresis

1160

(1)

24-5 Synthesis of Amino Acids

1161

(6)

Summary: Syntheses of Amino Acids

1166

(1)

24-6 Resolution of Amino Acids

1167

(1)

24-7 Reactions of Amino Acids

1167

(3)

Summary: Reactions of Amino Acids

1170

(1)

24-8 Structure and Nomenclature of Peptides and Proteins

1170

(4)

24-9 Peptide Structure Determination

1174

(6)

24-10 Solution-Phase Peptide Synthesis

1180

(3)

24-11 Solid-Phase Peptide Synthesis

1183

(5)

24-12 Classification of Proteins

1188

(1)

24-13 Levels of Protein Structure

1189

(2)

24-14 Protein Denaturation

1191

(2)

Chapter 24 Glossary

1193

(3)

Study Problems

1196

(4)

25 Lipids

1200

(22)

25-1 Introduction

1200

(1)

25-2 Waxes

1200

(1)

25-3 Triglycerides

1201

(3)

25-4 Saponification of Fats and Oils; Soaps and Detergents

1204

(4)

25-5 Phospholipids

1208

(1)

25-6 Steroids

1209

(3)

25-7 Prostaglandins

1212

(1)

25-8 Terpenes

1213

(4)

Chapter 25 Glossary

1217

(1)

Study Problems

1218

(4)

26 Synthetic Polymers

1222

(21)

26-1 Introduction

1222

(1)

26-2 Addition Polymers

1223

(6)

26-3 Stereochemistry of Polymers

1229

(1)

26-4 Stereochemical Control of Polymerization; Ziegler-Natta Catalysts

1230

(1)

26-5 Natural and Synthetic Rubbers

1230

(2)

26-6 Copolymers of Two or More Monomers

1232

(1)

26-7 Condensation Polymers

1232

(4)

26-8 Polymer Structure and Properties

1236

(2)

Chapter 26 Glossary

1238

(2)

Study Problems

1240

(3)

Appendices

1243

1A NMR Absorption Positions of Protons in Various Structural Environments

1244

(2)

1B Spin-Spin Coupling Constants

1246

(1)

1C 13C Chemical Shifts in Organic Compounds

1247

(1)

2A Characteristic Infrared Group Frequencies

1248

(3)

2B IR: Characteristic Infrared Absorptions of Functional Groups

1251

(2)

3 UV: The Woodward-Fieser Rules for Predicting UV-Visible Spectra

1253

(4)

4A Methods and Suggestions for Proposing Mechanisms

1257

(3)

4B Suggestions for Developing Multistep Syntheses

1260

(1)

5 pKa Values for Representative Compounds

1261

Answers to Selected Problems

Photo Credits

PC1

Index

Please wait while the item is added to your bag...

FREE SHIPPING

Amazon no longer offers textbook rentals. We do!

Organic Chemistry

Summary

Table of Contents

Supplemental Materials