Rent 9780471418030 | Organic Chemistry, 7th Edition Upgrade | T. W. Graham Solomons (Univ. of South Florida); Craig B. Fryhle (Pacific Lutheran Univ.) @knetbooks.com

Summary Table of Contents Author Biography

On the cover of this book is a Pacific yew tree, found in the ancient forests of the Pacific Northwest. The bark of the Pacific yew tree produces Taxol, found to be a highly effective drug against ovarian and breast cancer. Taxol blocks mitosis during eukaryotic cell division. The supply of Taxol from the Pacific yew tree is vanishingly small, however. A single 100-year-old tree provides only about one dose of the drug (roughly 300 mg). For this reason, as well as the spectacular molecular architecture of Taxol, synthetic organic chemists fierc... MORE

Carbon Compounds and Chemical Bonds

(49)

Life Is Organic Chemistry (Molecular graphic: Glycine, an organic molecule found in space)

(1)

... MORE

Introduction

(1)

The Development of Organic Chemistry as a Science

(1)

The Structural Theory of Organic Chemistry

(3)

Chemical Bonds: The Octet Rule

(2)

Writing Lewis Structures

(1)

Exceptions to the Octet Rule

(2)

Formal Charge

(2)

Resonance

(4)

Quantum Mechanics

(1)

Atomic Orbitals

(2)

Molecular Orbitals

(3)

The Structure of Methane and Ethane: sp3 Hybridization

(4)

The Structure of Ethene (Ethylene): sp2 Hybridization

(5)

The Structure of Ethyne (Acetylene): sp Hybridization

(2)

A Summary of Important Concepts that Come from Quantum Mechanics

(2)

Molecular Geometry: The Valence Shell Electron-Pair Repulsion (VSEPR) Model

(3)

Representation of Structural Formulas

(10)

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy

(40)

Structure Is Everything (Molecular graphic: Crixivan, a drug used against HIV)

(1)

Carbon--Carbon Covalent Bonds

(1)

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

(4)

Polar Covalent Bonds

(1)

Polar and Nonpolar Molecules

(3)

Functional Groups

(1)

Alkyl Halides or Haloalkanes

(1)

Alcohols

(2)

Ethers

(1)

Amines

(1)

Aldehydes and Ketones

(2)

Carboxylic Acids, Amides, and Esters

(1)

Nitriles

(1)

Summary of Important Families of Organic Compounds

(1)

Physical Properties and Molecular Structure

(8)

Summary of Attractive Electric Forces

(1)

Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups

(14)

An Introduction to Organic Reactions: Acids and Bases

(39)

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

(1)

Reactions and Their Mechanisms

(3)

Acid-Base Reactions

(4)

The Chemistry of... HOMOs and LUMOs in Reactions

(1)

Heterolysis of Bonds to Carbon: Carbocations and Carbanions

(1)

Use of Curved Arrows in Illustrating Reactions

(2)

The Strength of Acids and Bases: Ka and pKa

101

(3)

Predicting the Outcome of Acid--Base Reactions

104

(2)

The Relationship between Structure and Acidity

106

(4)

Energy Changes

110

(1)

The Relationship between the Equilibrium Constant and the Standard Free-Energy Change, ΔG°

111

(1)

The Acidity of Carboxylic Acids

112

(4)

The Effect of the Solvent on Acidity

116

(1)

Organic Compounds as Bases

117

(2)

A Mechanism for an Organic Reaction

119

(1)

Acids and Bases in Nonaqueous Solutions

120

(3)

The Chemistry of Carbonic Anhydrase

121

(2)

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

123

(6)

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

129

(55)

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

129

(1)

Introduction to Alkanes and Cycloalkanes

130

(2)

Shapes of Alkanes

132

(3)

IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols

135

(7)

Nomenclature of Cycloalkanes

142

(2)

Nomenclature of Alkenes and Cycloalkenes

144

(2)

Nomenclature of Alkynes

146

(1)

Physical Properties of Alkanes and Cycloalkanes

147

(2)

Sigma Bonds and Bond Rotation

149

(2)

Conformational Analysis of Butane

151

(2)

The Relative Stabilities of Cycloalkanes: Ring Strain

153

(2)

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

155

(2)

Conformations of Cyclohexane

157

(3)

Substituted Cyclohexanes: Axial and Equatorial Hydrogen Atoms

160

(3)

Disubstituted Cycloalkanes: Cis-Trans Isomerism

163

(5)

Bicyclic and Polycyclic Alkanes

168

(1)

Pheromones: Communication by Means of Chemicals

169

(1)

Chemical Reactions of Alkanes

170

(1)

Synthesis of Alkanes and Cycloalkanes

170

(3)

Some General Principles of Structure and Reactivity: A Look Toward Synthesis

173

(1)

An Introduction to Organic Synthesis

174

(10)

The Chemistry of... From the Inorganic to the Organic

178

(6)

Stereochemistry: Chiral Molecules

184

(45)

The Handeness of Life (Molecular graphic: The mirror-image stereoisomers of alanine, a chiral amino acid)

184

(1)

Isomerism: Constitutional Isomers and Stereoisomers

185

(2)

Enantiomers and Chiral Molecules

187

(4)

The Biological Importance of Chirality

191

(2)

The Historical Origin of Stereochemistry

193

(1)

Tests for Chirality: Planes of Symmetry

194

(1)

Nomenclature of Enantiomers: The (R--S) System

195

(5)

Properties of Enantiomers: Optical Activity

200

(5)

The Origin of Optical Activity

205

(3)

The Synthesis of Chiral Molecules

208

(2)

Chiral Drugs

210

(1)

The Chemistry of... Selective Binding of Drug Enantiomers to Left- and Right-hand Coiled DNA

211

(1)

Molecules with More Than One Stereocenter

211

(4)

Fischer Projection Formulas

215

(2)

Stereoisomerism of Cyclic Compounds

217

(2)

Relating Configurations through Reactions in Which No Bonds to the Stereocenter Are Broken

219

(4)

Separation of Enantiomers: Resolution

223

(1)

Compounds with Stereocenters Other than Carbon

224

(1)

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

224

(5)

Ionic Reactions---Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

229

(52)

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

229

(1)

Introduction

230

(1)

Physical Properties of Organic Halides

231

(1)

Nucleophilic Substitution Reactions

231

(1)

Nucleophiles

232

(1)

Leaving Groups

233

(1)

Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction

234

(1)

A Mechanism for the SN2 Reaction

235

(2)

Transition State Theory: Free-Energy Diagrams

237

(3)

The Stereochemistry of SN2 Reactions

240

(3)

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

243

(1)

A Mechanism for the SN1 Reaction

244

(2)

Carbocations

246

(3)

The Stereochemistry of SN1 Reactions

249

(2)

Factors Affecting the Rates of SN1 and SN2 Reactions

251

(10)

Organic Synthesis: Functional Group Transformations Using SN2 Reactions

261

(4)

The Chemistry of... Biological Methylation: A Biological Nucleophilic Substitution Reaction

262

(3)

Elimination Reactions of Alkyl Halides

265

(2)

The E2 Reaction

267

(1)

The E1 Reaction

268

(1)

Substitution versus Elimination

269

(3)

Overall Summary

272

(9)

Alkenes and Alkynes 1: Properties and Synthesis. Elimination Reactions of Alkyl Halides

281

(40)

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

281

(1)

Introduction

282

(1)

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

282

(2)

Relative Stabilities of Alkenes

284

(3)

Cycloalkenes

287

(1)

Synthesis of Alkenes via Elimination Reactions

288

(1)

Dehydrohalogenation of Alkyl Halides

288

(5)

Dehydration of Alcohols

293

(6)

Carbocation Stability and the Occurrence of Molecular Rearrangements

299

(4)

Alkenes by Debromination of Vicinal Dibromides

303

(1)

Synthesis of Alkynes by Elimination Reactions

304

(1)

The Acidity of Terminal Alkynes

305

(1)

Replacement of the Acetylenic Hydrogen Atom of Terminal Alkynes

306

(1)

Hydrogenation of Alkenes

307

(2)

The Chemistry of... Hydrogenation in the Food Industry

308

(1)

Hydrogenation: The Function of the Catalyst

309

(1)

Hydrogenation of Alkynes

310

(2)

Molecular Formulas of Hydrocarbons: The Index of Hydrogen Deficiency

312

(9)

Alkenes and Alkynes II: Addition Reactions

321

(45)

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

321

(1)

Introduction: Additions to Alkenes

322

(2)

Addition of Hydrogen Halides to Alkenes: Markovnikov's Rule

324

(6)

Stereochemistry of the Ionic Addition to an Alkene

330

(1)

Addition of Sulfuric Acid to Alkenes

330

(1)

Addition of Water to Alkenes: Acid-Catalyzed Hydration

331

(3)

Addition of Bromine and Chlorine to Alkenes

334

(1)

Stereochemistry of the Addition of Halogens to Alkenes

335

(4)

Halohydrin Formation

339

(3)

The Chemistry of... Regioselectivity in Unsymmetrically Substituted Bromonium Ions: Bromonium Ions of Ethene, Propene, and 2-Methylpropene

340

(2)

Divalent Carbon Compounds: Carbenes

342

(2)

Oxidations of Alkenes: Syn Hydroxylation

344

(2)

Oxidative Cleavage of Alkenes

346

(2)

Addition of Bromine and Chlorine to Alkynes

348

(1)

Addition of Hydrogen Halides to Alkynes

349

(1)

Oxidative Cleavage of Alkynes

350

(1)

Synthetic Strategies Revisited

350

(16)

The Chemistry of... Cholesterol Biosynthesis: Elegant and Familiar Reactions in Nature

354

(12)

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

366

(63)

A Thermos of Liquid Helium (Molecular graphic: 1-Chloro-2-propanol)

366

(1)

Introduction

367

(1)

The Electromagnetic Spectrum

368

(2)

Nuclear Magnetic Resonance Spectroscopy

370

(4)

Nuclear Spin: The Origin of the Signal

374

(2)

Shielding and Deshielding of Protons

376

(1)

The Chemical Shift

377

(2)

Chemical Shift Equivalent and Nonequivalent Protons

379

(2)

Signal Splitting: Spin - Spin Coupling

381

(10)

Proton NMR Spectra and Rate Processes

391

(2)

Carbon-13 NMR Spectroscopy

393

(4)

Two-Dimensional (2D) NMR Techniques

397

(6)

The Chemistry of... Magnetic Resonance Imaging in Medicine

402

(1)

An Introduction to Mass Spectrometry

403

(1)

The Mass Spectrometer

403

(3)

The Mass Spectrum

406

(3)

Determination of Molecular Formulas and Molecular Weights

409

(4)

Fragmentation

413

(7)

GC/MS Analysis

420

(1)

Mass Spectrometry of Biomolecules

420

(9)

Radical Reactions

429

(47)

Calicheamicin γII: A Radical Device for Slicing the Backbone of DNA (Molecular graphic: Calicheamicin γI1, a molecule capable of double-strand DNA cleavage, bound to DNA)

429

(2)

Introduction

431

(2)

The Chemistry of... Radicals in Biology, Medicine, and Industry

432

(1)

Homolytic Bond Dissociation Energies

433

(4)

The Reactions of Alkanes with Halogens

437

(2)

Chlorination of Methane: Mechanism of Reaction

439

(3)

Chlorination of Methane: Energy Changes

442

(8)

Halogenation of Higher Alkanes

450

(3)

The Geometry of Alkyl Radicals

453

(1)

Reactions that Generate Tetrahedral Stereocenters

453

(3)

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

456

(2)

Radical Polymerization of Alkenes: Chain-Growth Polymers

458

(2)

Other Important Radical Reactions

460

(16)

Special Topic A: Chain-Growth Polymers

469

(7)

Alcohols and Ethers

476

(53)

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

476

(1)

Structure and Nomenclature

477

(3)

Physical Properties of Alcohols and Ethers

480

(2)

Important Alcohols and Ethers

482

(2)

Synthesis of Alcohols from Alkenes

484

(1)

Alcohols from Alkenes through Oxymercuration - Demercuration

485

(3)

Hydroboration: Synthesis of Organoboranes

488

(2)

Alcohols from Alkenes through Hydroboration - Oxidation

490

(3)

Reactions of Alcohols

493

(1)

Alcohols as Acids

494

(1)

Conversion of Alcohols into Mesylates and Tosylates

495

(2)

Mesylates and Tosylates in SN2 Reactions

497

(2)

The Chemistry of... Alkyl Phosphates

498

(1)

Conversion of Alcohols into Alkyl Halides

499

(1)

Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides

499

(3)

Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCI2

502

(1)

Synthesis of Ethers

503

(4)

Reactions of Ethers

507

(1)

Epoxides

508

(4)

The Chemistry of... The Sharpless Asymmetric Epoxidation

510

(2)

Reactions of Epoxides

512

(4)

The Chemistry of... Epoxides, Carcinogens, and Biological Oxidation

514

(2)

Anti Hydroxylation of Alkenes via Epoxides

516

(3)

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

519

(4)

Summary of Reactions of Alkenes, Alcohols, and Ethers

523

(6)

Alcohols from Carbonyl Compounds. Oxidation - Reduction and Organometallic Compounds

529

(42)

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

529

(1)

Introduction

530

(2)

Oxidation - Reduction Reactions in Organic Chemistry

532

(1)

Alcohols by Reduction of Carbonyl Compounds

533

(5)

The Chemistry of... Alcohol Dehydrogenase

536

(1)

The Chemistry of... Stereoselective Reduction of Carbonyl Groups

537

(1)

Oxidation of Alcohols

538

(5)

Organometallic Compounds

543

(1)

Preparation of Organolithium and Organomagnesium Compounds

544

(2)

Reactions of Organolithium and Organomagnesium Compounds

546

(3)

Alcohols from Grignard Reagents

549

(7)

Lithium Dialkylcuprates: The Corey - Posner, Whitesides - House Synthesis

556

(3)

Protecting Groups

559

(12)

First Review Problem Set

566

(5)

Conjugated Unsaturated Systems

571

(48)

Molecules with the Nobel Prize in Their Synthetic Lineage (Molecular graphic: Morphine, the synthesis of which involved the Diels - Alder reaction)

571

(1)

Introduction

572

(1)

Allylic Substitution and the Allyl Radical

573

(4)

The Stability of the Allyl Radical

577

(3)

The Allyl Cation

580

(2)

Summary of Rules for Resonance

582

(4)

Alkadienes and Polyunsaturated Hydrocarbons

586

(1)

1,3-Butadiene: Electron Delocalization

587

(2)

The Stability of Conjugated Dienes

589

(2)

Ultraviolet - Visible Spectroscopy

591

(9)

The Chemistry of... The Photochemistry of Vision

596

(4)

Electrophilic Attack on Conjugated Dienes: 1,4 Addition

600

(4)

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

604

(15)

Aromatic Compounds

619

(42)

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

619

(1)

Introduction

620

(1)

Nomenclature of Benzene Derivatives

621

(2)

Reactions of Benzene

623

(1)

The Kekule Structure for Benzene

624

(2)

The Stability of Benzene

626

(1)

Modern Theories of the Structure of Benzene

627

(3)

Huckel's Rule: The (4n + 2) π Electron Rule

630

(7)

Other Aromatic Compounds

637

(5)

The Chemistry of... Nanotubes

641

(1)

Heterocyclic Aromatic Compounds

642

(1)

Aromatic Compounds in Biochemistry

643

(3)

Spectroscopy of Aromatic Compounds

646

(15)

The Chemistry of... Sunscreens (Catching the Sun's Rays and What Happens to Them)

650

(11)

Reactions of Aromatic Compounds

661

(53)

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

661

(1)

Electrophilic Aromatic Substitution Reactions

662

(1)

A General Mechanism for Electrophilic Aromatic Substitution: Arenium Ions

663

(2)

Halogenation of Benzene

665

(2)

Nitration of Benzene

667

(1)

Sulfonation of Benzene

668

(1)

Friedel - Crafts Alkylation

669

(2)

Friedel - Crafts Acylation

671

(2)

Limitations of Friedel - Crafts Reactions

673

(2)

Synthetic Applications of Friedel - Crafts Acylations: The Clemmensen Reduction

675

(2)

Effect of Substituents on Reactivity and Orientation

677

(3)

Theory of Substituent Effects on Electrophilic Aromatic Substitution

680

(12)

The Chemistry of... Iodine Incorporation in Thyroxine Biosynthesis

690

(2)

Reactions of the Side Chain of Alkylbenzenes

692

(4)

The Chemistry of... Industrial Styrene Synthesis

693

(3)

Alkenylbenzenes

696

(2)

Synthetic Applications

698

(4)

Allylic and Benzylic Halides in Nucleophilic Substitution Reactions

702

(2)

Reduction of Aromatic Compounds

704

(10)

Aldehydes and Ketones I: Nucleophilic Addition to the Carbonyl Group

714

(52)

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

714

(1)

Introduction

715

(1)

Nomenclature of Aldehydes and Ketones

716

(1)

Physical Properties

717

(2)

Synthesis of Aldehydes

719

(4)

Synthesis of Ketones

723

(4)

Nucleophilic Addition to the Carbon -- Oxygen Double Bond

727

(3)

The Addition of Alcohols: Hemiacetals and Acetals

730

(8)

The Addition of Derivatives of Ammonia

738

(5)

The Chemistry of... Pyridoxal Phosphate

742

(1)

The Addition of Hydrogen Cyanide

743

(2)

The Addition of Ylides: The Wittig Reaction

745

(4)

The Addition of Organometallic Reagents: The Reformatsky Reaction

749

(1)

Oxidation of Aldehydes and Ketones

750

(2)

Chemical Analysis for Aldehydes and Ketones

752

(1)

Spectroscopic Properties of Aldehydes and Ketones

753

(13)

Aldehydes and Ketones II. Aldol Reactions

766

(44)

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

766

(1)

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

767

(2)

Keto and Enol Tautomers

769

(1)

Reactions via Enols and Enolate Anions

770

(6)

The Aldol Reaction: The Addition of Enolate Anions to Aldehydes and Ketones

776

(4)

Crossed Aldol Reactions

780

(6)

Cyclizations via Aldol Condensations

786

(2)

Lithium Enolates

788

(6)

The Chemistry of... Silyl Enol Ethers

792

(2)

α-Selenation: A Synthesis of α,β-Unsaturated Carbonyl Compounds

794

(1)

Additions to α,β-Unsaturated Aldehydes and Ketones

795

(15)

The Chemistry of... Calicheamicin γI1 Activation for Cleavage of DNA

799

(11)

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

810

(67)

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

810

(1)

Introduction

811

(1)

Nomenclature and Physical Properties

811

(9)

Preparation of Carboxylic Acids

820

(2)

Nucleophilic Addition - Elimination at the Acyl Carbon

822

(3)

Acyl Chlorides

825

(2)

Carboxylic Acid Anhydrides

827

(1)

Esters

828

(8)

Amides

836

(8)

The Chemistry of... Penicillins

844

(1)

α-Halo Acids: The Hell - Volhard - Zelinski Reaction

844

(2)

Derivatives of Carbonic Acid

846

(3)

Decarboxylation of Carboxylic Acids

849

(2)

The Chemistry of... Thiamine

850

(1)

Chemical Tests for Acyl Compounds

851

(26)

Special Topic B: Step-Growth Polymers

868

(9)

Synthesis and Reactions of β-Dicarbonyl Compounds: More Chemistry of Enolate Anions

877

(65)

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

877

(1)

Introduction

878

(1)

The Claisen Condensation: The Synthesis of β-Keto Esters

879

(6)

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

885

(7)

The Malonic Ester Synthesis: Synthesis of Substituted Acetic Acids

892

(4)

Further Reactions of Active Hydrogen Compounds

896

(1)

Direct Alkylation of Esters and Nitriles

897

(1)

Alkylation of 1,3-Dithianes

898

(2)

The Knoevenagel Condensation

900

(1)

Michael Additions

900

(2)

The Chemistry of... A Suicide Enzyme Substrate

902

(1)

The Mannich Reaction

902

(2)

Synthesis of Enamines: Stork Enamine Reactions

904

(4)

Barbiturates

908

(34)

The Chemistry of... Antibody-Catalyzed Aldol Condensations

909

(14)

Special Topic C: Thiols, Sulfur Ylides, and Disulfides

923

(5)

Special Topic D: Thiol Esters and Lipid Biosynthesis

928

(14)

Amines

942

(72)

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

942

(2)

Nomenclature

944

(1)

Physical Properties and Structure of Amines

945

(2)

Basicity of Amines: Amine Salts

947

(8)

The Chemistry of... HPLC Resolution of Enantiomers

954

(1)

Some Biologically Important Amines

955

(2)

Preparation of Amines

957

(8)

Reactions of Amines

965

(1)

Reactions of Amines with Nitrous Acid

966

(3)

The Chemistry of... N-Nitrosoamines

968

(1)

Replacement Reactions of Arenediazonium Salts

969

(3)

Coupling Reactions of Arenediazonium Salts

972

(3)

Reactions of Amines with Sulfonyl Chlorides

975

(2)

The Sulfa Drugs: Sulfanilamide

977

(3)

Analysis of Amines

980

(2)

Eliminations Involving Ammonium Compounds

982

(32)

Special Topic E: Reactions and Synthesis of Heterocyclic Amines

997

(11)

Special Topic F: Alkaloids

1008

(6)

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

1014

(74)

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

1014

(1)

Structure and Nomenclature of Phenols

1015

(1)

Naturally Occurring Phenols

1016

(3)

The Chemistry of... Polyketide Anticancer Antibiotic Biosynthesis

1017

(2)

Physical Properties of Phenols

1019

(1)

Synthesis of Phenols

1019

(4)

Reactions of Phenols as Acids

1023

(2)

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

1025

(1)

Cleavage of Alkyl Aryl Ethers

1026

(1)

Reactions of the Benzene Ring of Phenols

1027

(2)

The Claisen Rearrangement

1029

(1)

Quinones

1030

(2)

Aryl Halides and Nucleophilic Aromatic Substitution

1032

(7)

The Chemistry of... Bacterial Dehalogenation of a PCB Derivative

1035

(4)

Spectroscopic Analysis of Phenols and Aryl Halides

1039

(49)

Second Review Problem Set

1050

(6)

Special Topic G: Electrocyclic and Cycloaddition Reactions

1056

(15)

Special Topic H: Organic Halides and Organometallic Compounds in the Environment

1071

(6)

Special Topic I: Transition Metal Organometallic Compounds

1077

(11)

Carbohydrates

1088

(54)

Carbohydrate Recognition in Healing and Disease (Molecular graphic: Sialyl Lewis, x a carbohydrate that is important in the recognition and healing of traumatized tissue)

1088

(1)

Introduction

1089

(3)

Monosaccharides

1092

(6)

Mutarotation

1098

(1)

Glycoside Formation

1099

(3)

Other Reactions of Monosaccharides

1102

(2)

Oxidation Reactions of Monosaccharides

1104

(6)

Reduction of Monosaccharides: Alditols

1110

(1)

Reactions of Monosaccharides with Phenylhydrazine: Osazones

1110

(2)

Synthesis and Degradation of Monosaccharides

1112

(2)

The D Family of Aldoses

1114

(1)

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

1114

(4)

Disaccharides

1118

(5)

The Chemistry of... Artificial Sweeteners (How Sweet It Is)

1122

(1)

Polysaccharides

1123

(5)

Other Biologically Important Sugars

1128

(1)

Sugars that Contain Nitrogen

1129

(1)

Glycolipids and Glycoproteins of the Cell Surface

1130

(2)

Carbohydrate Antibiotics

1132

(10)

Lipids

1142

(37)

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

1142

(1)

Introduction

1143

(1)

Fatty Acids and Triacylglycerols

1144

(8)

The Chemistry of... Olestra and Other Fat Substitutes

1148

(4)

Terpenes and Terpenoids

1152

(4)

Steroids

1156

(9)

Prostaglandins

1165

(2)

Phospholipids and Cell Membranes

1167

(3)

Waxes

1170

(9)

Amino Acids and Proteins

1179

(49)

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

1179

(1)

Introduction

1180

(1)

Amino Acids

1181

(5)

Laboratory Synthesis of α-Amino Acids

1186

(4)

Analysis of Polypeptides and Proteins

1190

(3)

Amino Acid Sequence of Polypeptides and Proteins

1193

(3)

Primary Structure of Polypeptides and Proteins

1196

(4)

The Chemistry of... Sickle Cell Anemia

1199

(1)

Polypeptide and Protein Synthesis

1200

(5)

Secondary, Tertiary, and Quaternary Structure of Proteins

1205

(7)

Introduction to Enzymes

1212

(1)

Lysozyme: Mode of Action of an Enzyme

1213

(2)

Serine Proteases

1215

(7)

The Chemistry of... Some Catalytic Antibodies

1220

(2)

Hemoglobin: A Conjugated Protein

1222

(6)

Nucleic Acids and Protein Synthesis

1228

(1)

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

1228

(1)

Introduction

1229

(1)

Nucleotides and Nucleosides

1229

(3)

Laboratory Synthesis of Nucleosides and Nucleotides

1232

(4)

Deoxyribonucleic Acid: DNA

1236

(7)

RNA and Protein Synthesis

1243

(7)

Determining the Base Sequence of DNA

1250

(3)

Laboratory Synthesis of Oligonucleotides

1253

(2)

The Polymerase Chain Reaction

1255

(3)

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

1258

Answers to Selected Problems

(1)

Glossary

(1)

Illustration and Photo Credits

(10)

Index

Appendix A

Upgrade Edition Additional Problems

(23)

Answers to Upgraded Edition Additional Problems

Craig B. Fryhle is affiliated with Pacific Lutheran University. T. W. Graham Solomons is affiliated with the University of South Florida.

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