Amazon no longer offers textbook rentals. We do!

Organic Chemistry A Short Course

by: Hart, Harold; Craine, Leslie E.; Hart, David J.

Organic Chemistry A Short Course

by: Hart, Harold; Craine, Leslie E.; Hart, David J.

ISBN 13:
9780618215362
ISBN 10:
0618215360
Edition: 11th
Format: Hardcover
Copyright: 07/18/2002
Publisher: Brooks Cole
Newer Edition

Rent

Sorry, this item is currently unavailable.

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

Extend or Purchase Your Rental at Any Time

Need to keep your rental past your due date? At any time before your due date you can extend or purchase your rental through your account.

Preface

xviii

To the Student

(5)

Bonding and Isomerism

(35)

How Electrons Are Arranged in Atoms

(2)

Ionic and Covalent Bonding

(3)

Ionic Compounds

(2)

The Covalent Bond

(1)

Carbon and the Covalent Bond

(2)

Carbon--Carbon Single Bonds

(1)

Polar Covalent Bonds

(1)

Multiple Covalent Bonds

(2)

Valence

(1)

Isomerism

(1)

Writing Structural Formulas

(2)

Abbreviated Structural Formulas

(2)

Formal Charge

(2)

Resonance

(1)

Arrow Formalism

(2)

The Orbital View of Bonding; the Sigma Bond

(1)

Carbon sp3 Hybrid Orbitals

(2)

Tetrahedral Carbon; the Bonding in Methane

(1)

Classification According to Molecular Framework

(1)

Acyclic Compounds

(1)

Carbocyclic Compounds

(1)

Heterocyclic Compounds

(1)

Classification According to Functional Group

(8)

Additional Problems

(4)

Alkanes and Cycloalkanes; Conformational and Geometric Isomerism

(30)

The Structures of Alkanes

(2)

Nomenclature of Organic Compounds

(1)

IUPAC Rules for Naming Alkanes

(2)

Alkyl and Halogen Substituents

(2)

Use of the IUPAC Rules

(1)

Sources of Alkanes

(1)

A Closer Look at Natural Gas

(1)

Physical Properties of Alkanes and Nonbonding Intermolecular Interactions

(2)

A Closer Look At Hydrogen Bonding

(1)

Conformations of Alkanes

(2)

Cycloalkane Nomenclature and Conformation

(4)

Cis--trans Isomerism in Cycloalkanes

(1)

Summary of Isomerism

(2)

A Word About Isomers, Possible and Impossible

(1)

Reactions of Alkanes

(4)

Oxidation and Combustion; Alkanes as Fuels

(2)

Halogenation of Alkanes

(1)

A Word About Methane, Marsh Gas, and Miller's Experiment

(1)

The Free-Radical Chain Mechanism of Halogenation

(6)

Reaction Summary

(1)

Mechanism Summary

(1)

Additional Problems

(4)

Alkenes and Alkynes

(45)

Definition and Classification

(2)

Nomenclature

(3)

Some Facts About Double Bonds

(1)

The Orbital Model of a Double Bond; the Pi Bond

(3)

Cis--trans Isomerism in Alkenes

(3)

A Word About The Chemistry of Vision

(2)

Addition and Substitution Reactions Compared

(1)

Polar Addition Reactions

(2)

Addition of Halogens

(1)

Addition of Water (Hydration)

(1)

Addition of Acids

(1)

Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov's Rule

(2)

Mechanism of Electrophilic Addition to Alkenes

(2)

Markovnikov's Rule Explained

(2)

Reaction Equilibrium: What Makes a Reaction Go?

(1)

Reaction Rates: How Fast Does a Reaction Go?

(3)

Hydroboration of Alkenes

(1)

Addition of Hydrogen

(1)

Additions to Conjugated Systems

(3)

Electrophilic Addition to Conjugated Dienes

(2)

Cycloaddition to Conjugated Dienes: The Diels--Alder Reaction

(1)

Free-Radical Additions; Polyethylene

(2)

Oxidation of Alkenes

101

(3)

Oxidation with Permanganate; a Chemical Test

101

(1)

Ozonolysis of Alkenes

101

(1)

A Word About Ethylene: Raw Material and Plant Hormone

102

(1)

Other Alkene Oxidations

103

(1)

Some Facts About Triple Bonds

104

(1)

The Orbital Model of a Triple Bond

104

(1)

Addition Reactions of Alkynes

105

(3)

A Word About Petroleum, Gasoline, and Octane Number

106

(2)

Acidity of Alkynes

108

(8)

A Closer Look At Petroleum

109

(1)

Reaction Summary

110

(1)

Mechanism Summary

111

(1)

Additional Problems

112

(4)

Aromatic Compounds

116

(30)

Some Facts About Benzene

117

(1)

The Kekule Structure of Benzene

118

(1)

Resonance Model for Benzene

119

(1)

Orbital Model for Benzene

119

(1)

Symbols for Benzene

120

(1)

Nomenclature of Aromatic Compounds

120

(3)

The Resonance Energy of Benzene

123

(2)

Electrophilic Aromatic Substitution

125

(1)

The Mechanism of Electrophilic Aromatic Substitution

126

(4)

Halogenation

127

(1)

Nitration

128

(1)

Sulfonation

128

(1)

Alkylation and Acylation

129

(1)

Ring-Activating and Ring-Deactivating Substituents

130

(1)

Ortho, Para-Directing, and Meta-Directing Groups

130

(5)

Ortho, Para-Directing Groups

131

(2)

Meta-Directing Groups

133

(2)

Substituent Effects on Reactivity

135

(1)

The Importance of Directing Effects in Synthesis

135

(1)

Polycyclic Aromatic Hydrocarbons

136

(10)

A Word About Polycyclic Aromatic Hydrocarbons and Cancer

137

(1)

A Word About C60, an Aromatic Sphere: The Fullerenes

138

(2)

A Closer Look At Polycyclic Aromatic Hydrocarbons

140

(1)

Reaction Summary

141

(1)

Mechanism Summary

142

(1)

Additional Problems

142

(4)

Stereoisomerism

146

(34)

Chirality and Enantiomers

146

(2)

Stereogenic Centers; the Stereogenic Carbon Atom

148

(4)

Configuration and the R--S Convention

152

(5)

The E--Z Convention for Cis--Trans Isomers

157

(1)

Polarized Light and Optical Activity

158

(4)

A Word About Pasteur's Experiments and the van't Hoff--LeBel Explanation

160

(2)

Properties of Enantiomers

162

(1)

Fischer Projection Formulas

163

(2)

Compounds with More Than One Stereogenic Center; Diastereomers

165

(2)

Meso Compounds; the Stereoisomers of Tartaric Acid

167

(2)

Stereochemistry: A Recap of Definitions

169

(1)

Stereochemistry and Chemical Reactions

170

(3)

A Word About Enantiomers and Biological Activity

172

(1)

Resolution of a Racemic Mixture

173

(7)

A Closer Look At Thalidomide

174

(1)

Additional Problems

175

(5)

Organic Halogen Compounds: Substitution and Elimination Reactions

180

(23)

Nucleophilic Substitution

180

(1)

Examples of Nucleophilic Substitutions

181

(4)

Nucleophilic Substitution Mechanisms

185

(1)

The SN2 Mechanism

185

(3)

The SN1 Mechanism

188

(2)

The SN1 and SN2 Mechanisms Compared

190

(3)

A Word About SN2 Reactions in Nature: Biological Methylations

192

(1)

Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms

193

(1)

Substitution and Elimination in Competition

194

(2)

Tertiary Halides

194

(1)

Primary Halides

195

(1)

Secondary Halides

195

(1)

Polyhalogenated Aliphatic Compounds

196

(7)

A Word About CFCs, the Ozone Layer, and Trade-Offs

198

(1)

A Word About Halogenated Organic Compounds from the Sea

199

(1)

Reaction Summary

199

(1)

Mechanism Summary

200

(1)

Additional Problems

200

(3)

Alcohols, Phenols, and Thiols

203

(28)

Nomenclature of Alcohols

203

(2)

A Word About Industrial Alcohols

205

(1)

Classification of Alcohols

205

(1)

Nomenclature of Phenols

206

(1)

Hydrogen Bonding in Alcohols and Phenols

206

(1)

Acidity and Basicity Reviewed

207

(3)

The Acidity of Alcohols and Phenols

210

(3)

The Basicity of Alcohols and Phenols

213

(1)

Dehydration of Alcohols to Alkenes

213

(2)

The Reaction of Alcohols with Hydrogen Halides

215

(1)

Other Ways to Prepare Alkyl Halides from Alcohols

216

(1)

A Comparison of Alcohols and Phenols

217

(1)

Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids

217

(3)

A Word About Biologically Important Alcohols and Phenols

219

(1)

Alcohols with More Than One Hydroxyl Group

220

(1)

Aromatic Substitution in Phenols

221

(2)

A Word About Quinones and the Bombardier Beetle

222

(1)

Oxidation of Phenols

223

(1)

Phenols as Antioxidants

223

(1)

Thiols, the Sulfur Analogs of Alcohols and Phenols

224

(7)

A Word About Hair, Curly or Straight

225

(1)

Reaction Summary

226

(1)

Additional Problems

227

(4)

Ethers and Epoxides

231

(19)

Nomenclature of Ethers

232

(1)

Physical Properties of Ethers

233

(1)

Ethers as Solvents

233

(1)

The Grignard Reagent; an Organometallic Compound

234

(3)

Preparation of Ethers

237

(2)

A Closer Look at MTBE

238

(1)

Cleavage of Ethers

239

(2)

A Word About Ether and Anesthesia

240

(1)

Epoxides (Oxiranes)

241

(2)

A Word About The Gypsy Moth's Epoxide

242

(1)

Reactions of Epoxides

243

(1)

Cyclic Ethers

244

(6)

Reaction Summary

246

(1)

Additional Problems

247

(3)

Aldehydes and Ketones

250

(33)

Nomenclature of Aldehydes and Ketones

251

(1)

Some Common Aldehydes and Ketones

252

(2)

Synthesis of Aldehydes and Ketones

254

(1)

Aldehydes and Ketones in Nature

255

(1)

The Carbonyl Group

256

(1)

Nucleophilic Addition to Carbonyl Groups: An Overview

257

(1)

Addition of Alcohols: Formation of Hemiacetals and Acetals

258

(4)

Addition of Water; Hydration of Aldehydes and Ketones

262

(1)

Addition of Grignard Reagents and Acetylides

262

(3)

Addition of Hydrogen Cyanide; Cyanohydrins

265

(1)

Addition of Nitrogen Nucleophiles

266

(1)

Reduction of Carbonyl Compounds

267

(1)

Oxidation of Carbonyl Compounds

268

(2)

Keto--Enol Tautomerism

270

(1)

Acidity of α-Hydrogens; the Enolate Anion

271

(1)

Deuterium Exchange in Carbonyl Compounds

272

(1)

The Aldol Condensation

273

(2)

The Mixed Aldol Condensation

275

(1)

A Word About Water Treatment and the Chemistry of Enols/Enolates

276

(1)

Commercial Syntheses via the Aldol Condensation

276

(7)

Reaction Summary

277

(2)

Mechanism Summary

279

(1)

Additional Problems

279

(4)

Carboxylic Acids and Their Derivatives

283

(38)

Nomenclature of Acids

283

(4)

Physical Properties of Acids

287

(1)

Acidity and Acidity Constants

287

(2)

What Makes Carboxylic Acids Acidic?

289

(1)

Effect of Structure on Acidity; the Inductive Effect Revisited

290

(1)

Conversion of Acids to Salts

291

(1)

Preparation of Acids

291

(5)

Oxidation of Primary Alcohols and Aldehydes

292

(1)

Oxidation of Aromatic Side Chains

292

(1)

Reaction of Grignard Reagents with Carbon Dioxide

293

(1)

Hydrolysis of Cyanides (Nitriles)

293

(2)

A Word About Green Chemistry and Ibuprofen: A Case Study

295

(1)

A Closer Look At Green Chemistry

296

(1)

Carboxylic Acid Derivatives

296

(1)

Esters

296

(1)

Preparation of Esters; Fischer Esterification

297

(1)

The Mechanism of Acid-Catalyzed Esterification; Nucleophilic Acyl Substitution

298

(2)

Lactones

300

(1)

Saponification of Esters

300

(1)

Ammonolysis of Esters

301

(1)

Reaction of Esters with Grignard Reagents

302

(1)

Reduction of Esters

303

(1)

The Need for Activated Acyl Compounds

303

(1)

Acyl Halides

304

(2)

Acid Anhydrides

306

(3)

A Word About Thioesters, Nature's Acyl-Activating Groups

308

(1)

Amides

309

(2)

A Summary of Carboxylic Acid Derivatives

311

(1)

The α-Hydrogen of Esters; the Claisen Condensation

312

(9)

Reaction Summary

315

(1)

Mechanism Summary

316

(1)

Additional Problems

316

(5)

Amines and Related Nitrogen Compounds

321

(27)

Classification and Structure of Amines

321

(2)

Nomenclature of Amines

323

(1)

Physical Properties and Intermolecular Interactions of Amines

324

(1)

Preparation of Amines; Alkylation of Ammonia and Amines

325

(2)

Preparation of Amines; Reduction of Nitrogen Compounds

327

(2)

The Basicity of Amines

329

(2)

Comparison of the Basicity and Acidity of Amines and Amides

331

(2)

Reaction of Amines with Strong Acids; Amine Salts

333

(2)

A Word About Alkaloids and the Dart-Poison Frogs

334

(1)

Chiral Amines as Resolving Agents

335

(1)

Acylation of Amines with Acid Derivatives

336

(2)

Quaternary Ammonium Compounds

338

(1)

Aromatic Diazonium Compounds

338

(3)

Diazo Coupling; Azo Dyes

341

(7)

Reaction Summary

343

(1)

Mechanism Summary

344

(1)

Additional Problems

344

(4)

Spectroscopy and Structure Determination

348

(32)

Principles of Spectroscopy

349

(1)

Nuclear Magnetic Resonance Spectroscopy (NMR)

350

(10)

Measuring an NMR Spectrum

351

(1)

Chemical Shifts and Peak Areas

352

(4)

Spin--Spin Splitting

356

(4)

13C NMR Spectroscopy

360

(2)

A Word About NMR in Biology and Medicine

362

(1)

Infrared Spectroscopy

362

(6)

Visible and Ultraviolet Spectroscopy

368

(2)

Mass Spectrometry

370

(10)

Additional Problems

374

(6)

Heterocyclic Compounds

380

(21)

Pyridine: Bonding and Basicity

380

(2)

Substitution in Pyridine

382

(3)

Other Six-Membered Heterocycles

385

(3)

Five-Membered Heterocycles: Furan, Pyrrole, and Thiophene

388

(2)

Electrophilic Substitution in Furan, Pyrrole, and Thiophene

390

(1)

Other Five-Membered Heterocycles: Azoles

391

(2)

A Word About Porphyrins: What Makes Blood Red and Grass Green?

392

(1)

Fused-Ring Five-Membered Heterocycles: Indoles and Purines

393

(8)

A Word About Morphine and Other Nitrogen-Containing Drugs

395

(2)

Reaction Summary

397

(1)

Mechanism Summary

398

(1)

Additional Problems

398

(3)

Synthetic Polymers

401

(26)

Classification of Polymers

401

(1)

Free-Radical Chain-Growth Polymerization

402

(5)

Cationic Chain-Growth Polymerization

407

(1)

Anionic Chain-Growth Polymerization

408

(1)

Stereoregular Polymers; Ziegler--Natta Polymerization

409

(2)

A Word About Polyacetylene and Conducting Polymers

411

(1)

Diene Polymers: Natural and Synthetic Rubber

411

(2)

Copolymers

413

(1)

Step-Growth Polymerization: Dacron and Nylon

414

(5)

A Word About Degradable Polymers

416

(1)

A Word About Aramids, the Latest in Polyamides

417

(1)

A Closer Look At Nylon

418

(1)

Polyurethanes and Other Step-Growth Polymers

419

(8)

Reaction Summary

422

(1)

Mechanism Summary

423

(1)

Additional Problems

424

(3)

Lipids and Detergents

427

(21)

Fats and Oils; Triesters of Glycerol

427

(4)

Hydrogenation of Vegetable Oils

431

(1)

Saponification of Fats and Oils; Soap

431

(1)

How Do Soaps Work?

432

(1)

Synthetic Detergents (Syndets)

433

(4)

A Word About Commercial Detergents

436

(1)

Phospholipids

437

(1)

Prostaglandins, Leukotrienes, and Lipoxins

438

(2)

A Word About Prostaglandins, Aspirin, and Pain

439

(1)

Waxes

440

(1)

Terpenes and Steroids

440

(8)

Reaction Summary

445

(1)

Additional Problems

445

(3)

Carbohydrates

448

(31)

Definitions and Classification

448

(1)

Monosaccharides

449

(1)

Chirality in Monosaccharides; Fischer Projection Formulas and D,L-Sugars

450

(4)

The Cyclic Hemiacetal Structures of Monosaccharides

454

(2)

Anomeric Carbons; Mutarotation

456

(1)

Pyranose and Furanose Structures

457

(1)

Conformations of Pyranoses

458

(1)

Esters and Ethers from Monosaccharides

459

(1)

Reduction of Monosaccharides

460

(1)

Oxidation of Monosaccharides

460

(1)

Formation of Glycosides from Monosaccharides

461

(2)

Disaccharides

463

(4)

Maltose

463

(1)

Cellobiose

464

(1)

Lactose

464

(1)

Sucrose

465

(1)

A Word About Sweetness and Sweeteners

466

(1)

Polysaccharides

467

(4)

Starch and Glycogen

467

(2)

Cellulose

469

(1)

A Word About Fat Substitutes from Carbohydrates

470

(1)

Other Polysaccharides

471

(1)

Sugar Phosphates

471

(1)

Deoxy Sugars

472

(1)

Amino Sugars

472

(1)

Ascorbic Acid (Vitamin C)

472

(7)

Reaction Summary

474

(1)

Additional Problems

475

(4)

Amino Acids, Peptides, and Proteins

479

(36)

Naturally Occurring Amino Acids

479

(4)

A Word About Amino Acid Dating

482

(1)

The Acid--Base Properties of Amino Acids

483

(3)

The Acid--Base Properties of Amino Acids with More Than One Acidic or Basic Group

486

(1)

Electrophoresis

487

(1)

Reactions of Amino Acids

488

(1)

The Ninhydrin Reaction

489

(1)

Peptides

489

(3)

A Word About Some Naturally Occurring Peptides

491

(1)

The Disulfide Bond

492

(1)

Proteins

492

(1)

The Primary Structure of Proteins

492

(4)

Amino Acid Analysis

493

(1)

Sequence Determination

494

(1)

Cleavage of Selected Peptide Bonds

495

(1)

The Logic of Sequence Determination

496

(3)

A Word About Protein Sequencing and Evolution

498

(1)

Peptide Synthesis

499

(4)

Secondary Structure of Proteins

503

(3)

Geometry of the Peptide Bond

503

(1)

Hydrogen Bonding

504

(1)

The α Helix and the Pleated Sheet

504

(2)

Tertiary Structure: Fibrous and Globular Proteins

506

(2)

Quaternary Protein Structure

508

(7)

Reaction Summary

509

(1)

Additional Problems

510

(5)

Nucleotides and Nucleic Acids

515

(25)

The General Structure of Nucleic Acids

515

(1)

Components of Deoxyribonucleic Acid (DNA)

516

(1)

Nucleosides

517

(2)

Nucleotides

519

(1)

The Primary Structure of DNA

520

(1)

Sequencing Nucleic Acids

521

(2)

A Word About DNA and Crime

522

(1)

Laboratory Synthesis of Nucleic Acids

523

(1)

Secondary DNA Structure; the Double Helix

523

(3)

DNA Replication

526

(1)

Ribonucleic Acids; RNA

527

(2)

The Genetic Code and Protein Biosynthesis

529

(5)

A Word About The Human Genome

531

(1)

A Word About Nucleic Acids and Viruses

532

(2)

Other Biologically Important Nucleotides

534

(6)

Reaction Summary

537

(1)

Additional Problems

537

(3)

Photo Credits

540

(1)

Appendix

541

(3)

Table A: Bond energies for the dissociation of selected bonds in the reaction A -- X → A . + X . (in kcal/mol)

541

(1)

Table B: Bond lengths of selected bonds (in angstroms, A)

541

(1)

Table C: Typical acidities of organic functional groups

542

(2)

Index/Glossary

544

Amazon no longer offers textbook rentals. We do!

Organic Chemistry A Short Course

Organic Chemistry A Short Course

9780618215362

0618215360

Table of Contents

Supplemental Materials

Write a Review

Amazon no longer offers textbook rentals. We do!

Organic Chemistry A Short Course

Organic Chemistry A Short Course

9780618215362

0618215360

Table of Contents

Supplemental Materials

Write a Review

Related Products