Organic Chemistry

by Brown, William H.; Foote, Christopher S.; Iverson, Brent L.

Edition:

4th

ISBN13:

9780534467739

ISBN10:

0534467733

Format:

Hardcover

Pub. Date:

10/21/2004

Publisher(s):

Brooks Cole

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Summary

This book provides an exciting introduction to organic chemistry for students majoring in chemistry and in related disciplines, especially the health and biological sciences. In this Fourth Edition, Brown, Foote, and Iverson build on the text's highly-praised hallmarks of unifying mechanistic themes, focusing on problem-solving, using applied problems from the pharmaceutical field, and making innovative use of color and emphasis on visualization. The new edition features increased coverage of mechanisms, more examples of bio-organic chemistry especially relevant to pre-medical students, new in-text learning aids including "How To" boxes, and state-of-the-art text/media integration with the Organic ChemistryNow Website.

Covalent Bonding and Shapes of Molecules

(55)

Electronic Structure of Atoms

(3)

Lewis Model of Bonding

(13)

How To Draw Lewis Structures From Condensed Structural Formulas

(2)

Chemical Connections The Octet Rule

(2)

Functional Groups

(5)

Bond Angles and Shapes of Molecules

(5)

Chemical Connections Fullerene---A New Form of Carbon

(1)

Polar and Nonpolar Molecules

(1)

Resonance

(5)

How To Draw Curved Arrows and Push Electrons

(4)

Quantum or Wave Mechanics

(3)

The Molecular Orbital and Valence Bond Theories of Covalent Bonding

(19)

Summary

(1)

Problems

(5)

Additional Problems

(3)

Alkanes and Cycloalkanes

(55)

The Structure of Alkanes

(1)

Constitutional Isomerism in Alkanes

(3)

Nomenclature of Alkanes

(4)

Cycloalkanes

(3)

The IUPAC System---A General System of Nomenclature

(2)

Conformations of Alkanes and Cycloalkanes

(14)

How To Draw Alternative Chair Conformations of Cyclohexane

(4)

Cis, Trans Isomerism in Cycloalkanes and Bicycloalkanes

(9)

How To Convert Planao Cyclohexanes to Chair Cyclohexanes

(4)

Chemical Connections The Poisonous Puffer Fish

(1)

Physical Properties of Alkanes and Cycloalkanes

(3)

Reactions of Alkanes

(3)

Sources and Importance of Alkanes

(12)

Chemical Connections Octane Rating: What Those Numbers at the Pump Mean

101

(1)

Summary

102

(1)

Key Reactions

103

(1)

Problems

103

(8)

Stereoisomerism and Chirality

111

(40)

Stereoisomerism

111

(1)

Chirality---The Handedness of Molecules

112

(4)

How To Draw Chiral Molecules

114

(2)

Naming Chiral Centers---The R,S System

116

(4)

How To Assign R or S Configuration to a Chiral Center

118

(2)

Acyclic Molecules with Two or More Chiral Centers

120

(5)

Cyclic Molecules with Two or More Chiral Centers

125

(5)

Properties of Stereoisomers

130

(1)

Optical Activity---How Chirality Is Detected in the Laboratory

130

(5)

Separation of Enantiomers---Resolution

135

(4)

Connections to Biological Chemistry Amino Acids

138

(1)

The Significance of Chirality in the Biological World

139

(12)

Connections to Biological Chemistry Chiral Drugs

141

(1)

Summary

142

(1)

Problems

143

(8)

Acids and Bases

151

(30)

Arrhenius Acids and Bases

151

(1)

Brønsted-Lowry Acids and Bases

152

(6)

Acid Dissociation Constants, pKa, and the Relative Strengths of Acids and Bases

158

(3)

The Position of Equilibrium in Acid-Base Reactions

161

(3)

Connections to Biological Chemistry

The Ionization of Functional Groups at Physiological pH

164

(1)

Molecular Structure and Acidity

164

(6)

Lewis Acids and Bases

170

(11)

Chemical Connections The Strongest Acid?

172

(1)

Summary

173

(1)

Key Reactions

174

(1)

Problems

174

(7)

Alkenes: Bonding, Nomenclature, and Properties

181

(23)

Structure of Alkenes

183

(3)

How To Calculate the Index of Hydrogen Deficiency

184

(2)

Nomenclature of Alkenes

186

(8)

Chemical Connections The Case of the Iowa and New York Strains of the European Corn Borer

193

(1)

Physical Properties of Alkenes

194

(1)

Naturally Occurring Alkenes---Terpene Hydrocarbons

194

(10)

Connections to Biological Chemistry

The Importance of cis Double Bonds in Fats Versus Oils

196

(2)

Summary

198

(1)

Problems

198

(6)

Reactions of Alkenes

204

(60)

Reactions of Alkenes---An Overview

205

(1)

Reaction Mechanisms

206

(3)

Electrophilic Additions

209

(20)

Hydroboration-Oxidation

229

(3)

Oxidation

232

(6)

How To Write a Balanced Half-Reaction

233

(5)

Reduction

238

(5)

Connections to Biological Chemistry

Trans Fatty Acids: What They Are and How to Avoid Them

242

(1)

Molecules Containing Chiral Centers as Reactants or Products

243

(21)

Summary

248

(1)

Key Reactions

249

(2)

Problems

251

(9)

Interchapter: Summary of Stereochemical Terms

260

(4)

Alkynes

264

(28)

Structure of Alkynes

264

(1)

Nomenclature of Alkynes

265

(2)

Physical Properties of Alkynes

267

(1)

Acidity of I-Alkynes

267

(1)

Preparation of Alkynes

268

(3)

Electrophilic Addition to Alkynes

271

(3)

Hydration of Alkynes to Aldehydes and Ketones

274

(5)

Reduction of Alkynes

279

(2)

Organic Synthesis: Retrosynthetic Analysis

281

(11)

Summary

284

(1)

Key Reactions

284

(2)

Problems

286

(6)

Haloalkanes, Halogenation, and Radical Reactions

292

(37)

Structure

292

(1)

Nomenclature

293

(2)

Physical Properties of Haloalkanes

295

(4)

Chemical Connections Freons

298

(1)

Preparation of Haloalkanes by Halogenation of Alkanes

299

(5)

Mechanism of Halogenation of Alkanes

304

(7)

Allylic Halogenation

311

(5)

Radical Autoxidation

316

(3)

Connections to Biological Chemistry Antioxidants

318

(1)

Radical Addition of HBr to Alkenes

319

(10)

Summary

321

(1)

Key Reactions

322

(1)

Problems

323

(6)

Nucleophilic Substitution and β-Elimination

329

(55)

Nucleophilic Substitution in Haloalkanes

330

(2)

Solvents for Nucleophilic Substitution Reactions

332

(2)

Mechanisms of Nucleophilic Aliphatic Substitution

334

(2)

Experimental Evidence for SN1 and SN2 Mechanisms

336

(15)

Analysis of Several Nucleophilic Substitution Reactions

351

(3)

β-Elimination

354

(2)

Mechanisms of β-Elimination

356

(2)

Experimental Evidence for E1 and E2 Mechanisms

358

(6)

Substitution Versus Elimination

364

(3)

Phase-Transfer Catalysis

367

(2)

Neighboring Group Participation

369

(15)

Connections to Biological Chemistry

Mustard Gases and the Treatment of Neoplastic Diseases

372

(1)

Summary

373

(1)

Key Reactions

374

(1)

Problems

375

(9)

Alcohols

384

(48)

Structure and Nomenclature of Alcohols

385

(3)

Physical Properties of Alcohols

388

(4)

Connections to Biological Chemistry

The Importance of Hydrogen Bonding in Drug-Receptor Interactions

390

(2)

Acidity and Basicity of Alcohols

392

(1)

Reaction of Alcohols with Active Metals

393

(1)

Conversion of Alcohols to Haloalkanes and Sulfonates

394

(7)

Acid-Catalyzed Dehydration of Alcohols

401

(5)

The Pinacol Rearrangement

406

(3)

Oxidation of Alcohols

409

(8)

Chemical Connections Blood Alcohol Screening

412

(2)

Connections to Biological Chemistry

The Oxidation of Alcohols by NAD+

414

(3)

Thiols

417

(15)

Summary

422

(1)

Key Reactions

422

(2)

Problems

424

(8)

Ethers, Sulfides, and Epoxides

432

(39)

Structure of Ethers

432

(1)

Nomenclature of Ethers

433

(1)

Physical Properties of Ethers

434

(2)

Preparation of Ethers

436

(4)

Reactions of Ethers

440

(3)

Silyl Ethers as Protecting Groups

443

(2)

Epoxides: Structure and Nomenclature

445

(1)

Synthesis of Epoxides

446

(5)

Reactions of Epoxides

451

(3)

Ethylene Oxide and Epichlorohydrin: Building Blocks in Organic Synthesis

454

(3)

Crown Ethers

457

(1)

Thioethers

458

(13)

Summary

460

(1)

Key Reactions

460

(3)

Problems

463

(8)

Infrared Spectroscopy

471

(22)

Electromagnetic Radiation

471

(2)

Molecular Spectroscopy

473

(1)

Infrared Spectroscopy

474

(5)

Interpreting Infrared Spectra

479

(10)

Solving Infrared Spectral Problems

489

(4)

Summary

489

(1)

Problems

490

(3)

Nuclear Magnetic Resonance Spectroscopy

493

(50)

Nuclear Spin States

494

(1)

Orientation of Nuclear Spins in an Applied Magnetic Field

494

(2)

Nuclear Magnetic Resonance

496

(2)

An NMR Spectrometer

498

(2)

Equivalent Hydrogens

500

(2)

Signal Areas

502

(2)

Chemical Shift

504

(4)

Signal Splitting and the (n + 1) Rule

508

(2)

The Origins of Signal Splitting

510

(8)

Stereochemistry and Topicity

518

(4)

Chemical Connections Magnetic Resonance Imaging

520

(2)

13C-NMR

522

(2)

The DEPT Method

524

(3)

Interpretation of NMR Spectra

527

(16)

How To Solve NMR Spectral Problems

530

(3)

Summary

533

(1)

Problems

534

(9)

Mass Spectrometry

543

(24)

A Mass Spectrometer

544

(3)

Features of a Mass Spectrum

547

(4)

Interpreting Mass Spectra

551

(10)

Connections to Biological Chemistry

Mass Spectrometry of Biological Macromolecules

560

(1)

Mass Spectrometry in the Organic Synthesis Laboratory and Other Applications

561

(6)

Summary

561

(1)

Problems

562

(5)

Organometallic Compounds

567

(17)

Organomagnesium and Organolithium Compounds

568

(5)

Lithium Diorganocopper (Gilman) Reagents

573

(3)

Carbenes and Carbenoids

576

(8)

Summary

580

(1)

Key Reactions

580

(1)

Problems

581

(3)

Aldehydes and Ketones

584

(61)

Structure and Bonding

584

(1)

Nomenclature

585

(4)

Physical Properties

589

(1)

Reactions

590

(1)

Addition of Carbon Nucleophiles

591

(5)

The Wittig Reaction

596

(4)

Addition of Oxygen Nucleophiles

600

(9)

Addition of Nitrogen Nucleophiles

609

(4)

Keto-Enol Tautomerism

613

(4)

Oxidation

617

(2)

Reduction

619

(6)

Connections to Biological Chemistry NADH: The Biological Equivalent of a Hydride Reducing Agent

620

(5)

Reactions at an α-Carbon

625

(20)

Summary

628

(1)

Key Reactions

628

(4)

Problems

632

(13)

Carboxylic Acids

645

(35)

Structure

645

(1)

Nomenclature

646

(3)

Physical Properties

649

(3)

Chemical Connections

From Willow Bark to Aspirin and Beyond

650

(2)

Acidity

652

(4)

Preparation of Carboxylic Acids

656

(2)

Reduction

658

(2)

Esterification

660

(5)

Chemical Connections

The Pyrethrins: Natural Insecticides of Plant Origin

662

(2)

Chemical Connections Esters as Flavoring Agents

664

(1)

Conversion to Acid Chlorides

665

(2)

Decarboxylation

667

(13)

Connections to Biological Chemistry

Ketone Bodies and Diabetes Mellitus

668

(2)

Summary

670

(1)

Key Reactions

670

(2)

Problems

672

(8)

Functional Derivatives of Carboxylic Acids

680

(50)

Structure and Nomenclature

681

(7)

Chemical Connections From Cocaine to Procaine and Beyond

683

(1)

Chemical Connections From Moldy Clover to a Blood Thinner

684

(2)

Chemical Connections The Penicillins and Cephalosporins: β-Lactam Antibiotics

686

(1)

Connections to Biological Chemistry The Unique Structure of Amide Bonds

687

(1)

Acidity of Amides, Imides, and Sulfonamides

688

(2)

Characteristic Reactions

690

(2)

Reaction with Water: Hydrolysis

692

(9)

Reaction with Alcohols

701

(3)

Reactions with Ammonia and Amines

704

(2)

Reaction of Acid Chlorides with Salts of Carboxylic Acids

706

(1)

Interconversion of Functional Derivatives

706

(1)

Reactions with Organometallic Compounds

707

(2)

Reduction

709

(21)

Summary

714

(1)

Key Reactions

714

(3)

Problems

717

(13)

Enolate Anions and Enamines

730

(53)

Formation and Reactions of Enolate Anions: An Overview

730

(2)

Aldol Reaction

732

(6)

Claisen and Dieckmann Condensations

738

(6)

Chemical Connections

Drugs That Lower Plasma Levels of Cholesterol

744

(1)

Claisen and Aldol Condensations in the Biological World

744

(3)

Enamines

747

(3)

Acetoacetic Ester Synthesis

750

(4)

Malonic Ester Synthesis

754

(4)

Chemical Connections Ibuprofen: The Evolution of an Industrial Synthesis

756

(2)

Conjugate Addition to α, β-Unsaturated Carbonyl Compounds

758

(25)

Summary

766

(1)

Key Reactions

766

(2)

Problems

768

(15)

Conjugated Systems

783

(18)

Stability of Conjugated Dienes

783

(4)

Electrophilic Addition to Conjugated Dienes

787

(6)

UV-Visible Spectroscopy

793

(8)

Chemical Connections Curry and Cancer

796

(2)

Summary

798

(1)

Key Reactions

798

(1)

Problems

798

(3)

Benzene and the Concept of Aromaticity

801

(56)

The Structure of Benzene

802

(4)

The Concept of Aromaticity

806

(12)

Nomenclature

818

(4)

Chemical Connections Carcinogenic Polynuclear Aromatic Hydrocarbons and Smoking

821

(1)

Phenols

822

(10)

Chemical Connections

Capsaicin, for Those Who Like It Hot

823

(9)

Reactions at a Benzylic Position

832

(25)

Summary

836

(1)

Key Reactions

836

(2)

Problems

838

(19)

Reactions of Benzene and Its Derivatives

857

(41)

Electrophilic Aromatic Substitution

858

(10)

Disubstitution and Polysubstitution

868

(8)

Nucleophilic Aromatic Substitution

876

(22)

Summary

880

(1)

Key Reactions

881

(2)

Problems

883

(15)

Amines

898

(54)

Structure and Classification

898

(2)

Nomenclature

900

(2)

Chirality of Amines and Quaternary Ammonium Ions

902

(2)

Physical Properties

904

(2)

Chemical Connections

The Poison Dart Frogs of South America

905

(1)

Basicity

906

(7)

Connections to Biological Chemistry

The Planarity of --- NH2 Groups on Aromatic Rings

910

(3)

Reactions with Acids

913

(4)

Preparation

917

(2)

Reaction with Nitrous Acid

919

(8)

Hofmann Elimination

927

(3)

Cope Elimination

930

(22)

Summary

931

(1)

Key Reactions

932

(3)

Problems

935

(17)

Carbon-Carbon Bond Formation and Synthesis

952

(48)

Carbon-Carbon Bond-Forming Reactions from Earlier Chapters

953

(1)

Organometallic Compounds

953

(1)

Organopalladium Reagents---The Heck Reaction

954

(7)

Organopalladium Reagents---The Suzuki Coupling

961

(2)

Alkene Metathesis

963

(3)

The Diels-Alder Reaction

966

(9)

Pericyclic Reactions and Transition State Aromaticity

975

(4)

Chemical Connections Singlet Oxygen

978

(1)

The Synthesis of Enantiomerically Pure Target Molecules

979

(21)

Summary

981

(1)

Key Reactions

981

(1)

Problems

982

(18)

Carbohydrates

1000

(36)

Monosaccharides

1001

(5)

The Cyclic Structure of Monosaccharides

1006

(5)

Chemical Connections L-Ascorbic Acid (Vitamin C)

1008

(3)

Reactions of Monosaccharides

1011

(6)

Chemical Connections Testing for Glucose

1016

(1)

Disaccharides and Oligosaccharides

1017

(4)

Chemical Connections

A, B, AB, and O Blood Group Substances

1020

(1)

Polysaccharides

1021

(3)

Chemical Connections High-Fructose Corn Syrup

1022

(2)

Acidic Polysaccharides

1024

(12)

Summary

1025

(1)

Key Reactions

1026

(2)

Problems

1028

(8)

Lipids

1036

(29)

Triglycerides

1036

(4)

Soaps and Detergents

1040

(2)

Prostaglandins

1042

(3)

Steroids

1045

(6)

Chemical Connections

Drugs That Lower Plasma Levels of Cholesterol

1050

(1)

Phospholipids

1051

(4)

Chemical Connections Snake Venom Phospholipases

1054

(1)

Fat-Soluble Vitamins

1055

(10)

Chemical Connections

Vitamin K, Blood Clotting, and Basicity

1058

(1)

Summary

1059

(1)

Problems

1060

(5)

Amino Acids and Proteins

1065

(39)

Amino Acids

1065

(4)

Acid-Base Properties of Amino Acids

1069

(5)

Polypeptides and Proteins

1074

(1)

Primary Structure of Polypeptides and Proteins

1075

(7)

Synthesis of Polypeptides

1082

(5)

Three-Dimensional Shapes of Polypeptides and Proteins

1087

(17)

Chemical Connections Spider Silk

1092

(3)

Summary

1095

(1)

Key Reactions

1096

(1)

Problems

1097

(7)

Nucleic Acids

1104

(25)

Nucleosides and Nucleotides

1105

(2)

The Structure of DNA

1107

(8)

Chemical Connections The Search for Antiviral Drugs

1109

(6)

Chemical Connections The Fountain of Youth

1115

(1)

Ribonucleic Acids

1115

(2)

The Genetic Code

1117

(3)

Sequencing Nucleic Acids

1120

(9)

Chemical Connections DNA Fingerprinting

1124

(1)

Summary

1125

(1)

Problems

1126

(3)

Organic Polymer Chemistry

1129

(1)

The Architecture of Polymers

1130

(1)

Polymer Notation and Nomenclature

1131

(1)

Molecular Weights of Polymers

1132

(1)

Polymer Morphology---Crystalline Versus Amorphous Materials

1132

(2)

Step-Growth Polymerizations

1134

(8)

Chemical Connections Stitches That Dissolve

1141

(1)

Chain-Growth Polymerizations

1142

(4)

Chemical Connections

Organic Polymers That Conduct Electricity

1146

(8)

Chemical Connections The Chemistry of Superglue

1154

(4)

Chemical Connections Recycling of Plastics

1158

(3)

Summary

1161

(1)

Key Reactions

1161

(1)

Problems

1162

Appendix 1 Thermodynamics and the Equilibrium Constant

(1)

Appendix 2 Major Classes of Organic Acids

(1)

Appendix 3 Bond Dissociation Enthalpies

(1)

Appendix 4 Characteristic 1H-NMR Chemical Shifts

(1)

Appendix 5 Characteristic 13C-NMR Chemical Shifts

(1)

Appendix 6 Characteristic Infrared Absorption Frequencies

(1)

Appendix 7 Electrostatic Potential Maps

Glossary

(1)

Index

Organic Chemistry

9780534467739

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