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Organic Chemistry:Short Course

by: Hart

Organic Chemistry:Short Course

by: Hart

ISBN 13:
9780395902257
ISBN 10:
0395902258
Edition: 10th
Format: Hardcover
Copyright: 01/01/1999
Publisher: Houghton Mifflin College Div
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Preface

xiv

To the Student

(5)

Bonding and Isomerism

(35)

How Electrons Are Arranged in Atoms

(2)

Ionic and Covalent Bonding

(4)

Ionic Compounds

(1)

The Covalent Bond

(2)

Carbon and the Covalent Bond

(1)

Carbon-Carbon Single Bonds

(1)

Polar Covalent Bonds

(2)

Multiple Covalent Bonds

(1)

Valence

(1)

Isomerism

(1)

Writing Structural Formulas

(2)

Abbreviated Structural Formulas

(2)

Formal Charge

(1)

Resonance

(2)

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

(2)

Acyclic Compounds

(1)

Carbocyclic Compounds

(1)

Heterocyclic Compounds

(1)

Classification According to Functional Group

(7)

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

(2)

A Word About: Isomers, Possible and Impossible

(1)

Physical Properties of Alkanes and Nonbonding Intermolecular Interactions

(2)

Conformations of Alkanes

(1)

Cycloalkane Nomenclature and Conformation

(5)

Cis--trans Isomerism in Cycloalkanes

(1)

Summary of Isomerism

(1)

Reactions of Alkanes

(3)

Oxidation and Combustion; Alkanes as Fuels

(1)

Halogenation of Alkanes

(2)

The Free-Radical Chain Mechanism of Halogenation

(7)

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

(3)

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

(2)

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

(1)

Cycloaddition to Conjugated Dienes: The Diels--Alder Reaction

(2)

Free-Radical Additions; Polyethylene

(1)

Oxidation of Alkenes

100

(4)

Oxidation with Permanganate; a Chemical Test

100

(1)

Ozonolysis of Alkenes

101

(2)

Other Alkene Oxidations

103

A Word About: Ethylene: Raw Material and Plant Hormone

102

(2)

Some Facts About Triple Bonds

104

(1)

The Orbital Model of a Triple Bond

104

(1)

Addition Reactions of Alkynes

105

(1)

Acidity of Alkynes

106

(10)

A Word About: Petroleum, Gasoline, and Octane Number

108

(2)

Reaction Summary

110

(2)

Mechanism Summary

112

(1)

Additional Problems

112

(4)

Aromatic Compounds

116

(29)

Some Facts About Benzene

117

(1)

The Kekule Structure of Benzene

118

(1)

The Resonance Model for Benzene

119

(1)

Orbital Model for Benzene

119

(1)

Symbols for Benzene

120

(1)

Nomenclature of Aromatic Compounds

121

(2)

The Resonance Energy of Benzene

123

(1)

Electrophilic Substitution

124

(1)

The Mechanism of Electrophilic Aromatic Substitution

125

(4)

Halogenation

127

(1)

Nitration

127

(1)

Sulfonation

128

(1)

Alkylation and Acylation

128

(1)

Ring-Activating and Ring-Deactivating Substituents

129

(1)

Ortho, Para-Directing, and Meta-Directing Groups

130

(4)

Ortho, Para-Directing Groups

130

(3)

Meta-Directing Groups

133

(1)

Substituent Effects on Reactivity

134

(1)

The Importance of Directing Effects in Synthesis

134

(1)

Polycyclic Aromatic Hydrocarbons

135

(10)

A Word About: Polycyclic Aromatic Hydrocarbons and Cancer

136

(2)

A Word About: C60, an Aromatic Sphere: The Fullerenes

138

(2)

Reaction Summary

140

(1)

Mechanism Summary

141

(1)

Additional Problems

141

(4)

Stereoisomerism

145

(34)

Chirality and Enantiomers

145

(2)

Stereogenic Centers; the Stereogenic Carbon Atom

147

(5)

Configuration and the R--S Convention

152

(4)

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

156

(1)

Polarized Light and Optical Activity

157

(5)

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

160

(2)

Properties of Enantiomers

162

(1)

Fischer Projection Formulas

163

(1)

Compounds with More Than One Stereogenic Center; Diastereomers

164

(2)

Meso Compounds; the Stereoisomers of Tartaric Acid

166

(2)

Stereochemistry: A Recap of Definitions

168

(2)

Stereochemistry and Chemical Reactions

170

(1)

Resolution of a Racemic Mixture

171

(8)

A Word About: Enantiomers and Biological Activity

172

(1)

Additional Problems

173

(6)

Organic Halogen Compounds; Substitution and Elimination Reactions

179

(25)

Nucleophilic Substitution

180

(1)

Examples of Nucleophilic Substitutions

180

(4)

Nucleophilic Substitution Mechanisms

184

(1)

The SN2 Mechanism

185

(3)

The SN1 Mechanism

188

(2)

The SN1 and SN2 Mechanisms Compared

190

(2)

Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms

192

(1)

Substitution and Elimination in Competition

193

(3)

Tertiary Halides

193

(1)

Primary Halides

194

(1)

Secondary Halides

194

(2)

A Word About: CFCs, the Ozone Layer, and Trade-offs

196

(1)

Polyhalogenated Aliphatic Compounds

196

(8)

A Word About: Insecticides and Herbicides

198

(2)

Reaction Summary

200

(1)

Mechanism Summary

200

(1)

Additional Problems

201

(3)

Alcohols, Phenols, and Thiols

204

(27)

Nomenclature of Alcohols

204

(1)

Classification of Alcohols

205

(1)

Nomenclature of Phenols

206

(1)

Hydrogen Bonding in Alcohols and Phenols

206

(2)

Acidity and Basicity Reviewed

208

(2)

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

(2)

Alcohols with More Than One Hydroxyl Group

219

(1)

Aromatic Substitution in Phenols

219

(2)

A Word About: Industrial Alcohols

220

(1)

Oxidation of Phenols

221

(3)

A Word About: Biologically Important Alcohols and Phenols

222

(2)

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

(18)

Nomenclature of Ethers

231

(1)

Physical Properties of Ethers

232

(1)

Ethers as Solvents

233

(1)

The Grignard Reagent; an Organometallic Compound

234

(2)

Preparation of Ethers

236

(2)

Cleavage of Ethers

238

(2)

A Word About: Ether and Anesthesia

239

(1)

Epoxides (Oxiranes)

240

(2)

A Word About: The Gypsy Moth's Epoxide

240

(2)

Reactions of Epoxides

242

(1)

Cyclic Ethers

243

(6)

Reaction Summary

245

(1)

Additional Problems

246

(3)

Aldehydes and Ketones

249

(34)

Nomenclature of Aldehydes and Ketones

250

(1)

Some Common Aldehydes and Ketones

251

(1)

Synthesis of Aldehydes and Ketones

252

(2)

A Word About: Quinones and the Bombardier Beetle

253

(1)

Aldehydes and Ketones in Nature

254

(1)

The Carbonyl Group

254

(2)

Nucleophilic Addition to Carbonyl Groups: An Overview

256

(2)

Addition of Alcohols: Formation of Hemiacetals and Acetals

258

(3)

Addition of Water; Hydration of Aldehydes and Ketones

261

(1)

Addition of Grignard Reagents and Acetylides

262

(2)

Addition of Hydrogen Cyanide; Cyanohydrins

264

(1)

Addition of Nitrogen Nucleophiles

265

(1)

Reduction of Carbonyl Compounds

266

(1)

Oxidation of Carbonyl Compounds

267

(2)

Keto--Enol Tautomerism

269

(2)

A Word About: Tautomerism and Photochromism

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)

Commercial Syntheses via the Aldol Condensation

275

(8)

Reaction Summary

276

(2)

Mechanism Summary

278

(1)

Additional Problems

278

(5)

Carboxylic Acids and Their Derivatives

283

(36)

Nomenclature of Acids

283

(4)

Physical Properties of Acids

287

(1)

Acidity and Acidity Constants

288

(1)

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

292

(2)

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

(1)

Carboxylic Acid Derivatives

294

(1)

Esters

295

(1)

Preparation of Esters; Fischer Esterification

296

(1)

The Mechanism of Acid-Catalyzed Esterification; Nucleophilic Acyl Substitution

296

(2)

Lactones

298

(1)

Saponification of Esters

299

(1)

Ammonolysis of Esters

300

(1)

Reaction of Esters with Grignard Reagents

300

(1)

Reduction of Esters

301

(1)

The Need for Activated Acyl Compounds

301

(1)

Acyl Halides

302

(2)

Acid Anhydrides

304

(3)

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

306

(1)

Amides

307

(2)

A Word About: Urea

309

(1)

A Summary of Carboxylic Acid Derivatives

309

(2)

The α-Hydrogen of Esters; the Claisen Condensation

311

(8)

Reaction Summary

313

(2)

Mechanism Summary

315

(1)

Additional Problems

315

(4)

Amines and Related Nitrogen Compounds

319

(29)

Classification and Structure of Amines

319

(1)

Nomenclature of Amines

320

(2)

Physical Properties and Intermolecular Interactions of Amines

322

(1)

Preparation of Amines; Alkylation of Ammonia and Amines

323

(2)

Preparation of Amines; Reduction of Nitrogen Compounds

325

(2)

The Basicity of Amines

327

(2)

Comparison of the Basicity and Acidity of Amines and Amides

329

(1)

Reaction of Amines with Strong Acids; Amine Salts

330

(3)

A Word About: Alkaloids and the Dart-Poison Frogs

332

(1)

Chiral Amines as Resolving Agents

333

(1)

Acylation of Amines with Acid Derivatives

334

(2)

Quaternary Ammonium Compounds

336

(1)

Aromatic Diazonium Compounds

336

(3)

Diazo Coupling; Azo Dyes

339

(9)

Reaction Summary

341

(2)

Mechanism Summary

343

(1)

Additional Problems

343

(5)

Spectroscopy and Structure Determination

348

(34)

Principles of Spectroscopy

349

(1)

Nuclear Magnetic Resonance Spectroscopy (NMR)

350

(11)

Measuring an NMR Spectrum

352

(1)

Chemical Shifts and Peak Areas

352

(5)

Spin--Spin Splitting

357

(4)

C NMR Spectroscopy

361

(3)

A Word About: NMR in Biology and Medicine

362

(2)

Infrared Spectroscopy

364

(5)

Visible and Ultraviolet Spectroscopy

369

(2)

Mass Spectrometry

371

(11)

Additional Problems

375

(7)

Heterocyclic Compounds

382

(22)

Pyridine: Bonding and Basicity

382

(2)

Substitution in Pyridine

384

(3)

Other Six-Membered Heterocycles

387

(2)

Five-Membered Heterocycles: Furan, Pyrrole, and Thiophene

389

(3)

Electrophilic Substitution in Furan, Pyrrole, and Thiophene

392

(1)

Other Five-Membered Heterocycles: Azoles

393

(3)

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

394

(2)

Fused-Ring Five-Membered Heterocycles: Indoles and Purines

396

(8)

A Word About: Morphine and Other Nitrogen-Containing Drugs

398

(2)

Reaction Summary

400

(1)

Mechanism Summary

401

(1)

Additional Problems

402

(2)

Synthetic Polymers

404

(25)

Classification of Polymers

404

(1)

Free-Radical Chain-Growth Polymerization

405

(6)

Cationic Chain-Growth Polymerization

411

(1)

Anionic Chain-Growth Polymerization

412

(1)

Stereoregular Polymers; Ziegler--Natta Polymerization

412

(2)

Diene Polymers: Natural and Synthetic Rubber

414

(2)

Copolymers

416

(1)

Step-Growth Polymerization: Dacron and Nylon

417

(3)

A Word About: Degradable Polymers

419

(1)

Polyurethanes and Other Step-Growth Polymers

420

(9)

A Word About: Aramids, the Latest in Polyamides

421

(3)

Reaction Summary

424

(1)

Mechanism Summary

425

(1)

Additional Problems

426

(3)

Lipids and Detergents

429

(22)

Fats and Oils; Triesters of Glycerol

429

(4)

Hydrogenation of Vegetable Oils

433

(1)

Saponification of Fats and Oils; Soap

433

(1)

How Do Soaps Work?

434

(2)

Synthetic Detergents (Syndets)

436

(4)

A Word About: Commercial Detergents

439

(1)

Phospholipids

440

(1)

Prostaglandins, Leukotrienes, and Lipoxins

440

(1)

Waxes

441

(1)

A Word About: Prostaglandins, Aspirin, and Pain

442

(1)

Terpenes and Steroids

442

(9)

Reaction Summary

447

(1)

Additional Problems

448

(3)

Carbohydrates

451

(31)

Definitions and Classification

451

(1)

Monosaccharides

452

(1)

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

453

(4)

The Cyclic Hemiacetal Structures of Monosaccharides

457

(2)

Anomeric Carbons; Mutarotation

459

(1)

Pyranose and Furanose Structures

460

(1)

Conformations of Pyranoses

461

(1)

Esters and Ethers from Monosaccharides

462

(1)

Reduction of Monosaccharides

463

(1)

Oxidation of Monosaccharides

463

(1)

Formation of Glycosides from Monosaccharides

464

(2)

Disaccharides

466

(4)

Maltose

466

(1)

Cellobiose

467

(1)

Lactose

467

(1)

Sucrose

468

(1)

A Word About: Sweetness and Sweeteners

468

(2)

Polysaccharides

470

(5)

Starch and Glycogen

470

(2)

Cellulose

472

(1)

Other Polysaccharides

473

(1)

A Word About: Fat Substitutes from Carbohydrates

474

(1)

Sugar Phosphates

475

(1)

Deoxy Sugars

475

(1)

Amino Sugars

475

(1)

Ascorbic Acid (Vitamin C)

476

(6)

Reaction Summary

477

(1)

Additional Problems

478

(4)

Amino Acids, Peptides, and Proteins

482

(37)

Naturally Occurring Amino Acids

482

(4)

A Word About: Amino Acid Dating

485

(1)

The Acid--Base Properties of Amino Acids

486

(3)

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

489

(2)

Electrophoresis

491

(1)

Reactions of Amino Acids

491

(1)

The Ninhydrin Reaction

492

(1)

Peptides

492

(2)

A Word About: Some Naturally Occurring Peptides

494

(1)

The Disulfide Bond

494

(2)

Proteins

496

(1)

The Primary Structure of Proteins

496

(4)

Amino Acid Analysis

496

(1)

Sequence Determination

497

(1)

Cleavage of Selected Peptide Bonds

498

(2)

The Logic of Sequence Determination

500

(2)

Peptide Synthesis

502

(5)

A Word About: Protein Sequencing and Evolution

503

(4)

Secondary Structure of Proteins

507

(4)

Geometry of the Peptide Bond

507

(1)

Hydrogen Bonding

508

(1)

The α Helix and the Pleated Sheet

508

(3)

Tertiary Structure: Fibrous and Globular Proteins

511

(2)

Quaternary Protein Structure

513

(6)

Reaction Summary

513

(1)

Additional Problems

514

(5)

Nucleotides and Nucleic Acids

519

(26)

The General Structure of Nucleic Acids

519

(1)

Components of Deoxyribonucleic Acid (DNA)

520

(1)

Nucleosides

521

(1)

Nucleotides

522

(2)

The Primary Structure of DNA

524

(1)

Sequencing Nucleic Acids

525

(2)

A Word About: DNA and Crime

526

(1)

Laboratory Synthesis of Nucleic Acids

527

(1)

Secondary DNA Structure; the Double Helix

528

(2)

DNA Replication

530

(2)

Ribonucleic Acids; RNA

532

(1)

The Genetic Code and Protein Biosynthesis

533

(3)

Other Biologically Important Nucleotides

536

(9)

A Word About: Nucleic Acids and Viruses

538

(3)

Reaction Summary

541

(1)

Additional Problems

541

(3)

Photo Credits

544

(1)

Appendix

545

(3)

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

545

(1)

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

545

(1)

Table C: Acidities of Organic Functional Groups

546

(2)

Index/Glossary

548

Amazon no longer offers textbook rentals. We do!

Organic Chemistry:Short Course

Organic Chemistry:Short Course

9780395902257

0395902258

Table of Contents

Supplemental Materials

Write a Review

Amazon no longer offers textbook rentals. We do!

Organic Chemistry:Short Course

Organic Chemistry:Short Course

9780395902257

0395902258

Table of Contents

Supplemental Materials

Write a Review

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