Organic Chemistry

, by Fox, Marye Anne; Whitesell, James K.

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ISBN: 9780763721978 | 0763721972
Cover: Hardcover
Copyright: 1/1/2004

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Supplemental Materials

Structure and Bonding in Alkanes

(42)

The Development and Study of Organic Chemistry

(4)

The Formation of Molecules

(14)

Atomic Structure

(4)

Bonding

(2)

Covalent Bonding

(5)

Ionic Bonding

(1)

Representing Molecules

(1)

Drawing Three-Dimensional Structures

(1)

Simple Hydrocarbons

(4)

Properties of Hydrocarbons

(1)

Alkanes (Saturated Hydrocarbons)

(1)

Structural Isomers

(2)

Cycloalkanes

(1)

Structures and Formulas

(2)

Ring Strain

Nomenclature

(4)

IUPAC Rules

(1)

Straight-Chain Hydrocarbons

(1)

Branched Hydrocarbons

(1)

Alkyl Groups

(3)

Cis and Trans Isomers

Alkane Stability

(28)

Heat of Combustion

(2)

Heat of Formation

(1)

Summary

(1)

Review Problems

(2)

Supplementary Problems

(3)

Alkenes, Aromatic Hydrocarbons, and Alkynes

(44)

Alkenes

(18)

Hybridization

(1)

Sigma Bonding

(1)

Pi Bonding

(1)

Molecular Orbitals

(4)

Structures of Alkenes

(3)

Isomerism in Alkenes

(1)

Nomenclature for Alkenes

(4)

Alkene Stability

(6)

Dienes and Polyenes

(2)

Aromatic Hydrocarbons

(11)

Resonance Structures

(2)

Stability

(2)

Aromaticity and Huckel's Rule

(2)

Arenes

(2)

Nomenclature for Aromatic Hydrocarbons

(2)

Alkynes

(11)

sp Hybridization

(1)

Higher Alkynes

(2)

Nomenclature for Alkynes

(1)

Allenes

(1)

Summary

(1)

Review of Reactions

(1)

Review Problems

(2)

Supplementary Problems

(4)

Functional Groups Containing Heteroatoms

(68)

Compounds Containing sp3-Hybridized Nitrogen

(5)

Ammonia: Hybridization and Geometry

(1)

Amines

(3)

Polar Covalent Bonding in Amines

(9)

Dipole Moments

(1)

Hydrogen Bonding

(2)

Solvation

(2)

Acidity and Basicity of Amines

(3)

Chemical Reactions

100

(1)

Compounds Containing sp2-Hybridized Nitrogen

101

(6)

Double Bonding at Nitrogen

101

(1)

Bond Strengths of Multiple Bonds

102

(1)

Calculating Oxidation Levels

103

(4)

Compounds Containing sp-Hybridized Nitrogen

107

(1)

Compounds Containing sp3-Hybridized Oxygen

108

(5)

Water

108

(1)

Alcohols: R---H

109

(3)

Ethers: R---O---R

112

(1)

Bond Cleavage

113

(11)

Homolytic Cleavage: Bond Energies and Radical Structure

115

(2)

Radical Stabilization

117

(1)

Heterolytic Cleavage of C---OH Bonds: Carbocation Formation

118

(2)

Cation Stabilization

120

(1)

Ordering Alcohol Reactivity by Class

120

(1)

Conjugation in Cations and Radicals

121

(3)

Bond Formation: Nucleophiles and Electrophiles

124

(1)

Carbonyl Compounds (Aldehydes and Ketones): R2C=O

125

(1)

Resonance Structures

126

(1)

Carboxylic Acids: RCO2H

126

(5)

Derivatives of Carboxylic Acids

127

(3)

Oxidation Levels 1

130

(1)

Sulfur-Containing Compounds

131

(2)

Aromatic Compounds Containing Heteroatoms

133

(5)

Biologically Important Heteroaromatics

134

(3)

Heteroatom-Substituted Arenes

137

(1)

Alkyl Halides

138

(2)

Solvents for Organic Chemistry

140

(1)

Nomenclature for Functional Groups

141

(13)

Summary

143

(2)

Review of Reactions

145

(1)

Review Problems

145

(2)

Supplementary Problems

147

(7)

Chromatography and Spectroscopy: Purification and Structure Determination

154

(62)

Using Physical Properties to Establish Structure

155

(2)

Purification of Compounds

156

(1)

Determination of Structure

157

(1)

Chromatography

157

(8)

Partitioning and Extraction

158

(1)

Liquid Chromatography on Stationary Columns

158

(2)

Detectors

160

(1)

Paper and Thin-Layer Chromatography

161

(1)

Reverse-Phase Chromatography

162

(1)

Gel Electrophoresis

162

(1)

Gas Chromatography

163

(2)

Spectroscopy

165

(51)

Nuclear Magnetic Resonance (NMR) Spectroscopy

166

(2)

13C NMR Spectroscopy

168

(3)

1H NMR Spectroscopy

171

(17)

Infrared (IR) Spectroscopy

188

(10)

Visible and Ultraviolet (UV) Spectroscopy

198

(7)

Mass Spectroscopy

205

(3)

Summary

208

(1)

Review Problems

209

(2)

Supplementary Problems

211

(5)

Stereochemistry

216

(52)

Geometric Isomerization: Rotation about Pi Bonds

218

(4)

Geometry of Alkenes

218

(1)

Energetics of Rotation about Pi Bonds

219

(1)

Reaction Energetics

220

(1)

Light-Induced Isomerization of Alkenes

221

(1)

Geometric Isomerization to the Less Stable Isomer

222

(1)

Conformational Analysis: Rotation about Sigma Bonds

222

(8)

Ethane

223

(2)

Butane

225

(5)

Cycloalkanes

230

(2)

Six-Member Carbon Rings

232

(9)

Cyclohexane

232

(4)

Monosubstituted Cyclohexanes

236

(2)

Disubstituted Cyclohexanes

238

(2)

Fused Six-Member Rings: Decalins

240

(1)

Chirality

241

(4)

Enantiomers

243

(1)

Representing Enantiomers in Two Dimensions

244

(1)

Absolute Configuration

245

(2)

Polarimetry

247

(4)

Optical Activity

248

(2)

Optical Purity

250

(1)

Designating Configuration

251

(6)

A Single Center of Chirality: Relative Configuration

251

(1)

Multiple Centers of Chirality: Absolute Configuration

252

(1)

Resolution of Enantiomers

253

(1)

Meso Compounds

254

(2)

Fischer Projections

256

(1)

Stereoisomerism at Heteroatom Centers

257

(1)

Optical Activity in Allenes

258

(10)

Summary

259

(1)

Review of Reactions

260

(1)

Review Problems

261

(2)

Supplementary Problems

263

(5)

Understanding Organic Reactions

268

(50)

Reaction Profiles (Energy Diagrams)

269

(4)

Free Energy

270

(1)

Thermodynamics: Initial and Final States

270

(1)

Kinetics: The Reaction Pathway

271

(1)

The Transition State

271

(1)

Reactive Intermediates

272

(1)

Thermodynamic Factors

273

(6)

Enthalpy Effects: Keto-Enol Tautomerization

274

(2)

Entropy Effects: The Diels-Alder Reaction

276

(3)

Characterizing Transition States: The Hammond Postulate

279

(1)

Types of Reactive Intermediates

279

(6)

Carbocations and Radicals

280

(1)

Carbanions

280

(2)

Carbenes

282

(1)

Radical Ions

283

(2)

Kinetics: Relative Rates from Reaction Profiles

285

(2)

Kinetic and Thermodynamic Control

287

(4)

Chemical Equilibria

291

(3)

Relating Free Energy to an Equilibrium Constant

291

(1)

Acid-Base Equilibria

292

(2)

Acidity

294

(11)

A Quantitative Measure of Thermodynamic Equilibria

294

(3)

Electronegativity

297

(1)

Bond Energies

297

(1)

Inductive and Steric Effects

297

(3)

Hybridization Effects

300

(1)

Resonance Effects

300

(2)

Enolate Anion Stability

302

(1)

Aromaticity

303

(2)

Reaction Rates: Understanding Kinetics

305

(13)

Unimolecular Reactions

306

(1)

Boltzmann Energy Distributions

307

(2)

Bimolecular Reactions

309

(1)

Summary

310

(1)

Review of Reactions

310

(1)

Review Problems

311

(3)

Supplementary Problems

314

(4)

Mechanisms of Organic Reactions

318

(52)

Classification of Reactions

320

(5)

Addition Reactions

320

(1)

Elimination Reactions

320

(1)

Substitution Reactions

321

(1)

Condensation Reactions

321

(1)

Le Chatelier's Principle

322

(1)

Rearrangement Reactions

322

(1)

Isomerization Reactions

323

(1)

Oxidation-Reduction Reactions

323

(1)

Reaction Mechanisms

324

(1)

Bond Making and Bond Breaking: Thermodynamic Feasibility

325

(4)

Energy Changes in Homolytic Reactions

325

(2)

Energy Changes in Heterolytic Reactions

327

(2)

How to Study a New Organic Reaction

329

(2)

Mechanism of a Concerted Reaction: Bimolecular Nucleophilic Substitution (SN2)

331

(11)

The Transition State of an SN2 Reaction

333

(2)

Inversion of Configuration

335

(1)

Nonsymmetrical SN2 Transition States

336

(1)

Factors Affecting the Rate of SN2 Reactions

337

(4)

Synthetic Utility of SN2 Reactions

341

(1)

Mechanism of Two Multistep Heterolytic Reactions: Electrophilic Addition and Nucleophilic Substitution (SN1)

342

(10)

Electrophilic Addition of HCl to an Alkene

342

(3)

Multistep Nucleophilic Substitution (SN1): Hydrolysis of Alkyl Bromides

345

(4)

Factors Affecting the Rate of SN1 Reactions

349

(1)

Rearrangements

350

(2)

Mechanism of a Multistep Homolytic Cleavage: Free-Radical Halogenation of Alkanes

352

(9)

Energetics of Homolytic Substitution in the Chlorination of Ethane

352

(1)

Steps in a Radical Chain Reaction

353

(2)

Relative Reactivity of Halogens

355

(2)

Regiocontrol in Homolytic Substitution

357

(4)

Synthetic Applications

361

(9)

Summary

363

(1)

Review Problems

364

(3)

Supplementary Problems

367

(3)

Substitution by Nucleophiles at sp3-Hybridized Carbon

370

(48)

Review of Mechanisms of Nucleophilic Substitution

372

(3)

SN2 Mechanism

372

(1)

SN1 Mechanism

372

(1)

Solvents for Organic Reactions

373

(2)

Competition between SN2 and SN1 Pathways

375

(2)

Functional-Group Transformations through SN2 and SN1 Reactions

377

(19)

Substitution of Halogen to Form Alcohols by an SN2 Mechanism

377

(2)

Substitution of Halogen to Form Alcohols by an SN1 Mechanism

379

(2)

Substitution of Halogen to Form Ethers: Williamson Ether Synthesis

381

(2)

Sulfonate Esters as Leaving Groups for Substitution Reactions

383

(1)

Substitution of Alcohols to Form Alkyl Halides

384

(4)

Substitution of Halogen to Form Thiols and Thioethers

388

(2)

Substitution of Halogen to Form Amines

390

(4)

Substitution of Halogen by Phosphines

394

(2)

Preparation and Use of Carbon Nucleophiles

396

(9)

Carbon Nucleophiles

397

(1)

General Methods for Preparation of Carbon Nucleophiles

397

(1)

sp-Hybridized Carbon Nucleophiles: Cyanide and Acetylide Anion

398

(2)

sp2- and sp3-Hybridized Carbon Nucleophiles: Organometallic Compounds

400

(3)

Reaction of Organometallic Compounds as Bases

403

(2)

Synthetic Methods: Functional-Group Conversion

405

(1)

Spectroscopy

405

(13)

Summary

409

(1)

Review of Reactions

410

(1)

Review Problems

411

(2)

Supplementary Problems

413

(5)

Elimination Reactions

418

(48)

Mechanistic Options for Elimination Reactions

420

(6)

E1 Mechanism: Carbocation Intermediates

420

(3)

E2 Mechanism: Synchronous Elimination

423

(1)

E1cB Mechanism: Carbanion Intermediates

423

(2)

Transition States and Reaction Profiles for E1 and E2 Eliminations

425

(1)

Dehydration of Alcohols

426

(2)

Dehydration via an E1 Mechanism

426

(1)

Dehydration via an E2 Mechanism

427

(1)

Dehydration via an E1cB Mechanism

427

(1)

Summary of Alcohol Dehydration Reactions

428

(1)

E2 Elimination Reactions: Dehydrohalogenation of Alkyl Halides

428

(9)

Transition State for E2 Elimination: Anti-periplanar Relationship

428

(1)

Stereochemistry of E2 Elimination Reactions

429

(2)

Regiochemistry of E2 Elimination Reactions

431

(1)

Effect of Reaction Conditions on Regiochemistry in E2 Reactions

431

(4)

Effect of Substrate Structure on the Regiochemistry of E2 Elimination in Cyclohexane Rings

435

(2)

Summary of E2 Elimination

437

(1)

E1 Elimination Reactions

437

(3)

Intermediate Cations in E1 Elimination Reactions

437

(1)

Stereochemistry of E1 Elimination Reactions

437

(1)

Factors Affecting Regioselectivity in E1 Reactions

438

(2)

Competing Rearrangements in E1 Reactions

440

(3)

E1 versus E2 Elimination

441

(1)

Substrate Structure

441

(1)

Leaving Groups

441

(2)

Elimination of X2

443

(1)

Elimination of HX from Vinyl Halides

443

(3)

E1 Elimination of HX from Vinyl Halides

444

(1)

E1cB and E2 Elimination of HX from Vinyl Halides

445

(1)

Preparation and Use of Vinyl Halides

445

(1)

Elimination of HX from Aryl Halides: Formation and Reactions of Benzyne

446

(2)

Mechanisms of Elimination from Aryl Halides

446

(1)

Structure of Benzyne

447

(1)

Reactions of Benzyne

447

(1)

Oxidation

448

(4)

Oxidation of Alcohols with Chromium Reagents

448

Functional Group Conversions Using Chromate Oxidations

(401)

Biological Oxidations

451

(1)

Oxidation of Hydrocarbons: Dehydrogenation

452

(3)

Direct Dehydrogenation

452

(1)

Laboratory-Scale Dehydrogenation

452

(3)

Synthetic Methods

455

(11)

Summary

457

(1)

Review of Reactions

458

(1)

Review Problems

458

(3)

Supplementary Problems

461

(5)

Addition to Carbon-Carbon Multiple Bonds

466

(56)

Electrophilic Addition of HC1, HBr, and H2O

Mechanism of Electrophilic Addition

468

(3)

Addition of HC1

471

(3)

Regiochemistry of Electrophilic Addition

474

(2)

Addition to Conjugated Dienes

476

(1)

Stereochemistry of Electrophilic Addition

477

(2)

Rearrangements

479

(1)

Addition of HX to Alkynes: Formation of Geminal Dihalides

480

(2)

Addition of Other Electrophiles

482

(8)

Oxymercuration--Demercuration

482

(3)

Hydration of Alkynes

485

(1)

Addition of Halogens

485

(4)

Carbocations as Electrophiles

489

(1)

Radical Additions

490

(3)

Radical Addition of HBr: Reversing Markovnikov Regiochemistry

490

(2)

Radical Polymerization

492

(1)

Cycloaddition Reactions

493

(14)

Synthesis of Cyclopropanes

493

(2)

Epoxidation

495

(2)

Four-Member Cyclic Transition State: Hydroboration-Oxidation

497

(3)

Five-Member Cyclic Intermediates

500

(3)

Formation of Six-Member Rings: The Diels-Alder Reaction

503

(2)

Stereochemistry in the Diels-Alder Reaction

505

(2)

Reduction of Multiple Bonds

507

(6)

Catalytic Hydrogenation

508

(3)

Dissolving-Metal Reductions

511

(2)

Synthetic Methods

513

(9)

Summary

515

(1)

Review of Reactions

516

(1)

Review Problems

517

(3)

Supplementary Problems

520

(2)

Electrophilic Aromatic Substitution

522

(48)

Mechanism of Electrophilic Aromatic Substitution

524

(1)

Step 1: Addition of the Electrophile and Formation of a Pentadienyl Cation as Intermediate

524

(1)

Step 2: Loss of a Proton

525

(1)

Introduction of Groups by Electrophilic Aromatic Substitution: Activated Electrophiles

525

(9)

Halogenation

526

(1)

Nitration

527

(1)

Sulfonation

528

(1)

Friedel-Crafts Alkylation

528

(4)

Friedel-Crafts Acylation

532

(2)

Reactions of Substituents and Side Chains of Aromatic Rings

534

(5)

Reduction of Nitro Groups to Primary Amines

534

(1)

Diazotization

535

(3)

Oxidation of Carbon Side Chains

538

(1)

Reactions of Aryl Side Chains

538

(1)

Substituent Effects in Aromatic Compounds: Reactivity and Orientation

539

(16)

Weakly Activating Substituents: Alkyl Groups

540

(4)

Strongly Activating Heteroatom Substituents

544

(2)

Moderately Activating Heteroatom Substituents

546

(1)

Moderately Deactivating Substituents: The Halogens

546

(2)

Moderately and Strongly Deactivating Substituents

548

(1)

Summary of Substituent Effects

549

(1)

Activating/Deactivating Versus Directing Effects

550

(1)

Multiple Substituents

551

(1)

Using Substituent Effects in Synthesis

552

(3)

Electrophilic Attack on Polycyclic Aromatic Compounds

555

(2)

Synthetic Applications

557

(3)

Spectroscopy

560

(10)

Summary

561

(1)

Review of Reactions

561

(1)

Review Problems

562

(2)

Supplementary Problems

564

(6)

Nucleophilic Addition and Substitution at Carbonyl Groups

570

(68)

Nucleophilic Addition to a Carbonyl Group

571

(5)

The Carbonyl Group

571

(2)

Possible Reactions of a Nucleophile with a Carbonyl Group

573

(1)

Anions as Nucleophiles

574

(2)

Nucleophilic Addition of Hydrogen to Carbonyl Groups

576

(8)

Complex Metal Hydride Reductions

576

(6)

Relative Reactivity of Carbonyl Compounds toward Hydride Reducing Agents

582

(2)

Oxygen Nucleophile

584

(9)

Addition of Water: Hydrate Formation

584

(3)

Addition of Hydroxide Ion: The Cannizzaro Reaction and Hydride Transfer

587

(2)

Addition of Alcohols

589

(4)

Nitrogen Nucleophiles

593

(6)

Amines

593

(4)

Other Nitrogen Nucleophiles

597

(2)

Nucleophilic Acyl Substitution of Carboxylic Acids and Derivatives

599

(11)

Relative Stability of Carboxylic Acid Derivatives

600

(1)

Interconversion of Carboxylic Acid Derivatives

601

(5)

Carboxylic Acid Chlorides

606

(3)

Reactions of Acid Anhydrides

609

(1)

Hydrolysis of Nitriles to Carboxylic Acids

609

(1)

Derivatives of Sulfonic and Phosphoric Acids

610

(3)

Sulfonic Acid Derivatives

610

(2)

Phosphoric Acid Derivatives

612

(1)

Carbon Nucleophiles

613

(8)

Cyanide Ion

613

(2)

Grignard Reagents

615

(3)

Organolithium Reagents

618

(1)

The Wittig Reaction

618

(3)

Synthetic Applications

621

(1)

Spectroscopy

621

(17)

Summary

626

(1)

Review of Reactions

627

(1)

Review Problems

628

(3)

Supplementary Problems

631

(7)

Substitution Alpha to Carbonyl Groups: Enolate Anions and Enols as Nucleophiles

638

(40)

Formation and Reactions of Enolate Anions and Enols

640

(7)

Molecular Orbitals of Enolate Anions

640

(1)

Structure of Enolate Anions

641

(1)

Protonation of Enolate Anions

641

(2)

Halogenation Alpha to Carbonyl Groups

643

(3)

Kinetic versus Thermodynamic Deprotonation of Carbonyl Groups

646

(1)

Alkylation of Ketones and Esters: SN2 Reaction with Alkyl Halides

647

(2)

Aldol Reaction, Aldol Condensation, and Related Reactions: Nucleophilic Addition of Enolate Anions to Carbonyl Groups

649

(9)

The Aldol Reaction

649

(1)

The Aldol Condensation

650

(1)

Aldol Reaction and Aldol Condensation of Ketones

650

(1)

Intramolecular Aldol Reaction and Aldol Condensation

651

(1)

Crossed Aldol Reaction

652

(2)

Nucleophilic Addition to α,ß-Unsaturated Carbonyl Groups: Conjugate Addition

654

(4)

The Claisen Condensation and Related Reactions: Acylation of Esters

658

(4)

The Claisen Condensation

658

(1)

The Dieckmann Condensation

659

(1)

Crossed Claisen Condensation

660

(1)

The Reformatsky Reaction

661

(1)

Alkylation of ß-Dicarbonyl Compounds

662

(7)

ß-Dicarbonyl Compounds

662

(1)

Alkylation of ß-Ketoesters

663

(1)

Alkylation of Malonic Acid Diesters

664

(1)

Hydrolysis and Decarboxylation of ß-Ketoesters and Malonic Acid Diesters

665

(2)

Acetoacetic Ester and Malonic Ester Syntheses

667

(1)

Formation of Carbocyclic Rings Using Acetoacetic Ester and Malonic Ester Syntheses

668

(1)

Synthetic Methods

669

(1)

Spectroscopy

669

(9)

Summary

672

(1)

Review of Reactions

673

(1)

Review Problems

673

(3)

Supplementary Problems

676

(2)

Skeletal-Rearrangement Reactions

678

(40)

Carbon-Carbon Rearrangements

679

(11)

Cationic Rearrangements

680

(4)

Anionic Rearrangements

684

(1)

Pericyclic Rearrangements

685

(5)

Carbon-Nitrogen Rearrangements

690

(5)

The Beckmann Rearrangement

691

(2)

The Hofmann Rearrangement

693

(2)

Carbon-Oxygen Rearrangements

695

(4)

The Baeyer-Villiger Oxidation

696

(2)

The Claisen Rearrangement

698

(1)

Synthetic Applications

699

(19)

Summary

700

(1)

Review of Reactions

700

(1)

Review of Reactions from Chapters 8--14

701

(10)

Review Problems

711

(2)

Supplementary Problems

713

(5)

Multistep Syntheses

718

(42)

Grouping Chemical Reactions

720

(4)

Retrosynthetic Analysis

724

(2)

Designing a Synthesis by Working Backward

724

(1)

Rationale for Retrosynthetic Analysis

724

(2)

Reactions Requiring Both Functional-Group Transformation and Skeletal Construction

726

(2)

Extending the Retrosynthetic Approach: Alternative Routes for Synthesizing

More Complex Molecules

728

(1)

Analyzing Individual Reactions in a Sequence

728

(1)

Order of Chemical Transformations

728

(2)

Selecting the Best Synthetic Route

730

(3)

Criteria for Evaluating Synthetic Efficiency

733

(4)

Linear Synthesis

733

(1)

Convergent Synthesis

734

(1)

Logistical Factors

735

(2)

Real-World Synthetic Objectives

737

(4)

Multifunctional Compounds

737

(2)

Functional-Group Compatibility

739

(2)

Protecting Groups

741

(5)

Protection of Aldehydes and Ketones

741

(1)

Requirements for the Use of Protecting Groups

742

(1)

Protection of Alcohols

743

(1)

Protection of Carboxylates

743

(1)

Protection of Amines

744

(1)

Use of an Alcohol Protecting Group

745

(1)

Practical Examples of Multistep Syntheses

746

(14)

Phenylpropionic Acid Analogs: Ibuprofen and Ketoprofen

746

(2)

Benzodiazepines: Valium

748

(4)

Summary

752

(1)

Review of Reactions

752

(1)

Review Problems

753

(2)

Supplementary Problems

755

(5)

Polymeric Materials

760

(42)

Monomers and Polymers

761

(2)

Linear and Branched Polymers

763

(2)

Types of Polymerization

765

(1)

Addition Polymerization

765

(11)

Radical Polymerization

765

(2)

Ionic Polymerization

767

(5)

Cross-Linking in Polymers

772

(1)

Heteroatom-Containing Addition Polymers

773

(3)

Condensation Polymers

776

(7)

Polyesters

776

(1)

Polysaccharides

777

(2)

Polyamides

779

(2)

Polypeptides

781

(1)

Polyurethanes

782

(1)

Extensively Cross-Linked Polymers

783

(3)

Three-Dimensional Structure of Polymers

786

(16)

Polypropylene

786

(2)

Naturally Occurring Polypeptides

788

(7)

Cellulose and Starch

795

(2)

Summary

797

(1)

Review of Reactions

798

(1)

Review Problems

798

(3)

Supplementary Problems

801

(1)

Naturally Occurring Oxygen-Containing Compounds

802

(44)

Lipids

803

(16)

Fats and Waxes

803

(11)

Terpenes

814

(4)

Steroids

818

(1)

Biosynthesis

819

(6)

Biosynthesis of Terpenes

820

(1)

Phosphates as Leaving Groups

821

(1)

Biosynthetic Pathways Involving Phosphates

822

(2)

Biosynthetic Pathways Involving Epoxides

824

(1)

Carbohydrates

825

(8)

Trioses

826

(1)

Aldotetroses

827

(1)

Aldopentoses

828

(2)

Aldohexoses

830

(2)

Ketoses

832

(1)

Dimeric and Polymeric Carbohydrates

833

(13)

Summary

837

(1)

Review of Reactions

838

(1)

Review Problems

839

(2)

Supplementary Problems

841

(5)

Naturally Occurring Nitrogen-Containing Compounds

846

(46)

Methods for Forming Carbon-Nitrogen Bonds: A Review

847

(6)

Amines via Nucleophilic Substitution

848

(1)

Amides

848

(1)

Imines

849

(1)

The Mannich Condensation

850

(2)

Amines via Nitrile Reduction

852

(1)

The Beckmann Rearrangement of Oximes: Amides from Carbonyl Compounds

852

(1)

Amino Acids: Structure and Properties

853

(5)

Structure of Amino Acids

853

(1)

Properties of Amino Acids

854

(4)

Polypeptides: Structure, Function, and Synthesis

858

(9)

Structure and Function of Polypeptides

585

(275)

Synthesis of Polypeptides

860

(7)

Alkaloids: Structure and Biological Activity

867

(3)

Structure of Nucleic Acids

870

(5)

Polynucleotide Backbone

871

(1)

Nucleic Acid Bases

871

(1)

Attachment of Base to Sugar

872

(2)

Sugar-Phosphate Linkages

874

(1)

Aminocarbohydrates: Structure and Function

875

(1)

Abiotic Synthesis

876

(16)

Adenine

877

(4)

Carbohydrates (Ribose)

881

(2)

Summary

883

(1)

Review of Reactions

883

(1)

Review Problems

884

(2)

Supplementary Problems

886

(6)

Noncovalent Interactions and Molecular Recognition

892

(30)

Nonpolar (Hydrophobic) Interactions

893

(2)

Influence of van der Waals Interactions on Physical Properties

834

(60)

Strength of van der Waals Interactions

894

(1)

Origin of van der Waals Interactions

895

(1)

Polar Interactions

895

(13)

Dipole-Dipole Interactions

895

(2)

Hydrogen Bonds

897

(5)

Metal-Heteroatom Bonds

902

(6)

Genetic Coding

908

(6)

Hydrogen Bonding in Biopolymers

908

(1)

Complementary Base Pairing

909

(1)

Replication

910

(1)

Coding Requirements

911

(1)

Reading the Genetic Code

912

(1)

Misreading the Genetic Code

913

(1)

Molecular Recognition of Chiral Molecules

914

(8)

Necessity of Three-Point Contact for Chiral Recognition

914

(3)

Resolution of Enantiomers

917

(1)

Biological Significance of Chirality

917

(2)

Summary

919

(1)

Review Problems

919

(2)

Supplementary Problems

921

(1)

Catalyzed Reactions

922

(42)

General Concepts of Catalysis

925

(5)

Transition-State Stabilization

925

(2)

Effect of Solvation on SN2 Reactions

927

(3)

Avoiding Charge Separation in Multistep Reactions

930

(5)

Intermolecular Proton Transfer

933

(1)

Proton Transfer via Charge Relay

934

(1)

Distinction between Catalysis and Induction

935

(3)

Base Catalysis

938

(1)

Comparison of Intermolecular and Intramolecular Reactions

939

(2)

Transition-Metal Catalysis

941

(8)

Catalytic Addition of Hydrogen to Alkenes

941

(5)

Catalysis of Olefin Polymerization

946

(3)

Catalysis by Enzymes

949

(15)

Enzyme-Substrate Binding

949

(1)

Catalysis by the Enzyme Chymotrypsin

950

(2)

Stabilization of Transition States by Enzymes

952

(1)

Enzymes and Chiral Recognition

953

(3)

Artificial Enzymes: Catalytic Antibodies

956

(3)

Summary

959

(1)

Review Problems

960

(2)

Supplementary Problems

962

(2)

Cofactors for Biological Reactions

964

(30)

Molecular Recognition

966

(1)

Recycling of Biological Reagents

966

(2)

Cofactors: Chemical Reagents for Biological Transformations

968

(1)

Cofactors for Redox Reactions

969

(7)

Pyridoxamine Phosphate

969

(3)

NADPH

972

(2)

FADH2

974

(2)

Acetyl CoA: Cofactor for Acyl Transfer

976

(1)

The Role of Thiol Esters

976

(1)

Activation of Carboxylic Acids (as Thiol Esters) toward Nucleophilic Attack

976

(1)

Tetrahydrofolic Acid: A One-Carbon Transfer Cofactor for Methylation of Nucleic Acids

977

(4)

Structure and Function of Tetrahydrofolic Acid

977

(2)

Transfer of a Methylene Fragment

979

(1)

Reductive Methylation of Deoxyuridylic Acid to Form Deoxythymidylic Acid

980

(1)

Thiamine Pyrophosphate and Lipoic Acid: Cofactors for the Decarboxylation of a-Ketoacids

981

(3)

Mechanisms of Decarboxylation

982

(1)

Structure and Function of the Cofactors Thiamine z Pyrophosphate and Lipoic Acid

982

(1)

Decarboxylation of α-Ketoacids in Biological Systems

983

(1)

Mimicking Biological Activation with Reverse-Polarity Reagents

984

(10)

Analysis of Carbon Reactivity

985

(1)

Analysis of Carbon Reactivity in ß-Ketoesters

986

(1)

Analysis of Carbon Reactivity in α-Ketoesters

987

(1)

Reversal of Reactivity

988

(2)

Summary

990

(1)

Review Problems

990

(2)

Supplementary Problems

992

(2)

Energy Storage in Organic Molecules

994

(44)

Reaction Energetics

995

(5)

Kinetics and Thermodynamics

995

(2)

Catalysis

997

(1)

Multistep Transformations

998

(2)

Complex Reaction Cycles

1000

(1)

Energy in Living Organisms

1000

(1)

Energy Transfer via Phosphoric Acid Anhydrides

1001

(2)

Energy Transfer through Redox Reactions

1003

(1)

Energy Storage in Fatty Acid Biosynthesis

1004

(5)

Carbon-Carbon Bond Formation

1004

(2)

Reduction

1006

(1)

Synthesis of Longer Chains

1007

(2)

Energy Release in Fatty Acid Degradation

1009

(1)

The Krebs Cycle: Release and Transfer of Energy from Acetate

1010

(7)

Oxidative Decarboxylation: Overview of the Krebs Cycle

1010

(3)

Prochiral Centers in Citric Acid

1013

(1)

Energy Transfer

1014

(3)

Maximizing the Efficiency of Energy Release by Controlling Heat Release

1017

(2)

Energy Release from Carbohydrates through Glycolysis

1019

(12)

Isomerization of Glucose to Fructose

1020

(1)

Cleavage of Fructose into Three-Carbon Fragments

1021

(4)

Conversion of the Three-Carbon Fragments into Acetic Acid Derivatives

1025

(6)

Biological Reactions in Energy Storage and Utilization

1031

(7)

Summary

1033

(1)

Review Problems

1034

(2)

Supplementary Problems

1036

(2)

Molecular Basis for Drug Action

1038

(43)

Chemical Basis of Disease States

1040

(3)

Intact Biological Systems as Chemical Factories

1043

(1)

H2 Blockers: Modern Antacids

1044

(2)

Neurologically Active Drugs: ß-Phenethylamines

1046

(3)

Antibiotics

1049

(12)

Blocking Synthesis of Tetrahydrofolic Acid

1049

(3)

Disruption of Membrane Structure and Interference with Ion Balance across Membranes

1052

(2)

Disruption of Bacterial Cell Walls

1054

(7)

Antiviral Agents

1061

(4)

Viral Structure

1061

(1)

Viral Attack on Cells

1061

(2)

Viral Replication: The ``Coup de Grace''

1063

(1)

Antiviral Therapy: Looking for a ``Magic Bullet''

1063

(2)

Prions

1065

(2)

Identification of Disease-Causing Agents

1065

(1)

Diseases Caused by Prions

1066

(1)

Protein Misfolding and Alzheimer's Disease

1066

(1)

Cancer Chemotherapy

1067

(10)

Characteristics of Cancer

1067

(1)

Causes of Cancer

1068

(1)

Treatment of Cancer: Chemotherapeutic Agents

1068

(1)

Drugs Affecting Nucleic Acid Synthesis

1069

(5)

Photochemotherapy

1074

(3)

Organic Chemistry: Retrospective and Prospects

1077

(4)

Summary

1078

(1)

Review Problems

1078

(3)

Appendix

1081

(10)

Glossary

1091

(22)

Index

1113

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