Organic Chemistry : A Brief Introduction

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ISBN: 9780138419332 | 0138419337
Cover: Paperback
Copyright: 8/28/1997

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Discussing difficult concepts with exceptional clarity, this book integrates synthetic organic chemistry with medical, pharmaceutical, and biological chemistry, and helps readers clearly define the relationship of organic chemistry to their particular occupation.The book provides numerous problems, exercises, and examples of the physical and chemical properties of bio-organic molecules, and presents complex organic structures on a continual basis throughout, enabling users to focus on relevant functional groups before covering advanced material on chemical reactions. It includes an extensive two-chapter review of general chemistry and offers chapter essays to examine material in greater depth.For nursing, agriculture, and other health and life science professionals.

Preface

1 Structure of Organic Compounds

(35)

1.1 Inorganic and Organic Compounds

(1)

1.2 Atomic Structure

(1)

1.3 Atomic Properties

(2)

1.4 Types of Bonds

(3)

1.5 Formal Charge

(2)

1.6 Resonance Structures

(2)

1.7 Predicting the Shapes of Simple Molecules

(2)

1.8 Orbitals and Molecular Shapes

(4)

1.9 Functional Groups

(3)

1.10 Structural Formulas

(5)

1.11 Isomers

(3)

1.12 Nomenclature

(1)

Explorations with Molecular Models

(1)

Exercises

Essay Pheromones--Chemical Communications in the Insect World

2 Properties of Organic Compounds

(33)

2.1 Structure and Physical Properties

(5)

2.2 Chemical Reactions

(2)

2.3 Acid-Base Reactions

(2)

2.4 Oxidation-Reduction Reactions

(3)

2.5 Classification of Organic Reactions

(2)

2.6 Chemical Equilibrium

(1)

2.7 Equilibria in Acid-Base Reactions

(3)

2.8 Structure and Acidity

(2)

2.9 Reaction Mechanisms

(2)

2.10 Reaction Rates

(4)

Explorations with Molecular Models

(1)

Exercises

Essays

Water-Soluble and Fat-Soluble Vitamins

Redox Reactions in Biochemistry

3 Alkanes and Cycloalkanes

(32)

3.1 Classes of Hydrocarbons

(1)

3.2 Alkanes

(2)

3.3 Nomenclature of Alkanes

(4)

3.4 Conformations of Alkanes

(3)

3.5 Cycloalkanes

(3)

3.6 Conformations of Cycloalkanes

(3)

3.7 Physical Properties of Saturated Hydrocarbons

(2)

3.8 Oxidation of Alkanes and Cycloalkanes

(2)

3.9 Halogenation of Saturated Hydrocarbons

(2)

3.10 Nomenclature of Haloalkanes

(3)

Summary of Reactions

(1)

Explorations with Molecular Models

(1)

Exercises

Essays

Steroids

Freons, Free Radicals, and the Ozone Layer

4 Alkenes and Alkynes

101

(37)

4.1 Unsaturated Hydrocarbons

101

(4)

4.2 Geometric Isomerism

105

(2)

4.3 The E,Z Designation of Geometric Isomers

107

(2)

4.4 Nomenclature of Alkenes and Alkynes

109

(3)

4.5 Acidity of Alkenes and Alkynes

112

(1)

4.6 Hydrogenation of Alkenes and Alkynes

113

(3)

4.7 Oxidation of Alkenes and Alkynes

116

(1)

4.8 Addition Reactions of Alkenes and Alkynes

117

(2)

4.9 Mechanism of Addition Reactions

119

(2)

4.10 Hydration of Alkenes and Alkynes

121

(1)

4.11 Polymerization of Alkenes

122

(2)

4.12 Preparation of Alkenes and Alkynes

124

(2)

4.13 Alkadienes

126

(2)

4.14 Terpenes

128

(1)

Summary of Reactions

129

(2)

Explorations with Molecular Models

131

(1)

Exercises

132

Essay Allylic Oxidation in Metabolic Reactions

127

5 Aromatic Compounds

138

(33)

5.1 Substituted Benzene Compounds

138

(1)

5.2 Aromaticity

139

(2)

5.3 Polycyclic and Heterocyclic Aromatic Compounds

141

(4)

5.4 Nomenclature of Benzene Compounds

145

(3)

5.5 Electrophilic Aromatic Substitution

148

(3)

5.6 Structural Effects in Electrophilic Aromatic Substitution

151

(2)

5.7 Interpretation of Rate Effects

153

(2)

5.8 Interpretation of Directing Effects

155

(2)

5.9 Reactions of Side Chains

157

(3)

5.10 Functional Group Modification

160

(2)

5.11 Synthesis of Substituted Aromatic Compounds

162

(2)

Summary of Reactions

164

(2)

Explorations with Molecular Models

166

(1)

Exercises

166

Essay Substituent Effects on Metabolism of Benzene Derivatives

158

6 Stereochemistry

171

(25)

6.1 Configuration of Molecules

171

(1)

6.2 Mirror Images and Chirality

172

(4)

6.3 Optical Activity

176

(2)

6.4 Fischer Projection Formulas

178

(2)

6.5 Absolute Configuration

180

(4)

6.6 Multiple Stereogenic Centers

184

(4)

6.7 Synthesis of Stereoisomers

188

(2)

6.8 Reactions of Chiral Compounds

190

(1)

Explorations with Molecular Models

191

(1)

Exercises

192

Essay

Metabolism May Vary By Species and Within Species

186

Chirality and Your Senses

189

7 Nucleophilic Substitution and Elimination Reactions

196

(21)

7.1 Reaction Mechanisms and Haloalkanes

196

(2)

7.2 Nucleophilic Substitution Reactions

198

(3)

7.3 Nucleophilicity versus Basicity

201

(1)

7.4 Mechanisms of Substitution Reactions

202

(5)

7.5 S(N)2 Versus S(N)1 Reactions

207

(2)

7.6 Mechanisms of Elimination Reactions

209

(1)

7.7 Effect of Structure on Competing Reactions

210

(3)

Summary of Reactions

213

(1)

Explorations with Molecular Models

213

(1)

Exercises

214

Essays

Halogen Compounds in Ocean Organisms

199

Biological Substitution Reactions with Sulfur Compounds

203

8 Alcohols and Phenols

217

(31)

8.1 The Hydroxyl Group

217

(2)

8.2 Classification and Nomenclature of Alcohols

219

(2)

8.3 Physical Properties of Alcohols

221

(2)

8.4 Acid-Base Reactions of Alcohols

223

(2)

8.5 Substitution Reactions of Alcohols

225

(1)

8.6 Dehydration of Alcohols

226

(2)

8.7 Oxidation of Alcohols

228

(1)

8.8 Synthesis of Alcohols

229

(6)

8.9 Phenols

235

(3)

8.10 Sulfur Compounds

238

(2)

Summary of Reactions

240

(2)

Explorations with Molecular Models

242

(1)

Exercises

242

Essays

Toxicity of Alcohols

230

Industrial Synthesis of Alcohols

236

Phenols are Germicides

239

9 Ethers and Epoxides

248

(18)

9.1 Ethers

248

(1)

9.2 Nomenclature of Ethers

249

(2)

9.3 Physical Properties of Ethers

251

(1)

9.4 The Grignard Reagent and Ethers

252

(2)

9.5 Synthesis of Ethers

254

(1)

9.6 Reactions of Ethers

255

(2)

9.7 Synthesis of Epoxides

257

(1)

9.8 Reactions of Epoxides

257

(4)

Summary of Reactions

261

(1)

Explorations with Molecular Models

262

(1)

Exercises

263

Essays

Polyethers in the Laboratory and in Nature

253

Ring Opening of Biological Epoxides

260

10 Aldehydes and Ketones

266

(33)

10.1 The Carbonyl Group

266

(2)

10.2 Nomenclature of Aldehydes and Ketones

268

(4)

10.3 Physical Properties of Aldehydes and Ketones

272

(1)

10.4 Redox Reactions of Carbonyl Compounds

273

(3)

10.5 Addition Reactions of Carbonyl Compounds

276

(2)

10.6 Synthesis of Alcohols from Carbonyl Compounds

278

(2)

10.7 Addition of Oxygen Compounds

280

(3)

10.8 Formation of Acetals and Ketals

283

(2)

10.9 Addition of Nitrogen Compounds

285

(2)

10.10 Reactivity of the ALPHA-Carbon Atom

287

(2)

10.11 The Aldol Condensation

289

(3)

Summary of Reactions

292

(1)

Explorations with Molecular Models

293

(1)

Exercises

294

Essays

Oral Contraceptives

281

Addition Reactions and Vision

286

11 Carbohydrates

299

(31)

11.1 Classification of Carbohydrates

299

(1)

11.2 Chirality of Monosaccharides

300

(6)

11.3 Hemiacetals and Hemiketals

306

(4)

11.4 Conformations of Monosaccharides

310

(2)

11.5 Reduction of Monosaccharides

312

(1)

11.6 Oxidation of Carbohydrates

313

(1)

11.7 Glycosides

314

(2)

11.8 Disaccharides

316

(5)

11.9 Polysaccharides

321

(3)

Summary of Reactions

324

(1)

Explorations with Molecular Models

325

(1)

Exercises

325

Essays

Metabolism of Lactose

320

Human Blood Groups

323

12 Carboxylic Acids and Esters

330

(37)

12.1 The Carboxyl and Acyl Groups

330

(2)

12.2 Nomenclature of Carboxylic Acid Derivatives

332

(4)

12.3 Physical Properties of Carboxylic Acids and Esters

336

(4)

12.4 Acidity of Carboxylic Acids

340

(2)

12.5 Synthesis of Carboxylic Acids

342

(2)

12.6 Nucleophilic Acyl Substitution

344

(4)

12.7 Reduction of Acyl Derivatives

348

(3)

12.8 Synthesis of Esters

351

(1)

12.9 Hydrolysis of Esters

352

(4)

12.10 The Claisen Condensation

356

(2)

Summary of Reactions

358

(1)

Explorations with Molecular Models

359

(1)

Exercises

360

Essays

Industrial Synthesis of Acetic Acid

337

Thioesters Are Nature's Active Acyl Compounds

348

Polyesters

352

Esters and Anhydrides of Phosphoric Acid

354

13 Lipids

367

(22)

13.1 Classification of Lipids

367

(1)

13.2 Waxes

368

(1)

13.3 Fatty Acids

369

(2)

13.4 Triacylglycerols

371

(2)

13.5 Hydrogenation of Vegetable Oils

373

(1)

13.6 Saponification of Triacylglycerols

374

(2)

13.7 Glycerophospholipids

376

(2)

13.8 Sphingophospholipids

378

(1)

13.9 Glycosphingolipids

379

(1)

13.10 Biological Membranes

380

(3)

13.11 Transport Across Membranes

383

(2)

Summary of Reactions

385

(1)

Explorations with Molecular Models

385

(1)

Exercises

386

Essays

Prostaglandins

372

Sleep Disorders and Brain Lipids

384

14 Amines and Amides

389

(30)

14.1 Organic Nitrogen Compounds

389

(2)

14.2 Structure and Classification of Amines and Amides

391

(2)

14.3 Nomenclature of Amines and Amides

393

(3)

14.4 Physical Properties of Amines and Amides

396

(2)

14.5 Basicity of Nitrogen Compounds

398

(5)

14.6 Solubility of Ammonium Salts

403

(1)

14.7 Nucleophilic Reactions of Amines

404

(2)

14.8 Synthesis of Amines

406

(2)

14.9 Hydrolysis of Amides

408

(1)

14.10 Synthesis of Amides

409

(2)

Summary of Reactions

411

(1)

Explorations with Molecular Models

412

(1)

Exercises

413

Essays

Amphetamines

399

Polyamides

410

15 Amino Acids, Peptides, and Proteins

419

(28)

15.1 Proteins and Polypeptides

419

(1)

15.2 Amino Acids

420

(1)

15.3 Acid-Base Properties of Amino Acids

421

(3)

15.4 Isoionic Point

424

(3)

15.5 Peptides

427

(3)

15.6 Synthesis of Peptides

430

(2)

15.7 Structure Determination of Proteins

432

(4)

15.8 Structure of Proteins

436

(7)

Explorations with Molecular Models

443

(1)

Exercises

444

Essays

Essential Amino Acids and Dietary Protein

426

Cholesterol and Lipoproteins

442

16 Nucleic Acids

447

(24)

16.1 The Control of Life Processes

447

(1)

16.2 Nucleic Acids Are Polymers

448

(3)

16.3 Polynucleotides

451

(3)

16.4 The Double Helix of DNA

454

(1)

16.5 DNA Replicates Itself

455

(2)

16.6 The Flow of Genetic Information

457

(1)

16.7 DNA Produces Several Types of RNA

458

(3)

16.8 The Genetic Code

461

(1)

16.9 Protein Synthesis and Translation

462

(6)

Explorations with Molecular Models

468

(1)

Exercises

469

Essay Chemistry and Medicine

464

17 Synthetic Polymers

471

(24)

17.1 Natural and Synthetic Macromolecules

471

(1)

17.2 Structure and Properties of Polymers

472

(3)

17.3 Classification of Polymers

475

(1)

17.4 Methods of Polymerization

476

(3)

17.5 Addition Polymerization

479

(2)

17.6 Copolymerization of Alkenes

481

(1)

17.7 Cross-linked Polymers

482

(1)

17.8 Stereochemistry of Addition Polymerization

483

(2)

17.9 Condensation Polymers

485

(1)

17.10 Polyesters

486

(1)

17.11 Polycarbonates

487

(1)

17.12 Polyamides

488

(2)

17.13 Polyurethanes

490

(1)

Explorations with Molecular Models

491

(1)

Exercises

491

Essay Polyurethanes in Treatment of Cancer

490

18 Spectroscopy

495

(31)

18.1 Structure Determination

495

(1)

18.2 Spectroscopy

496

(2)

18.3 Ultraviolet Spectroscopy

498

(2)

18.4 Infrared Spectroscopy

500

(7)

18.5 Nuclear Magnetic Resonance Spectroscopy

507

(4)

18.6 Spin-Spin Splitting

511

(3)

18.7 (13)C NMR Spectroscopy

514

(6)

Explorations with Molecular Models

520

(1)

Exercises

521

Essay Magnetic Resonance Imaging

515

Answers to Problems

526

(4)

Answers to Odd-Numbered Exercises

530

(17)

Index

547

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Organic Chemistry : A Brief Introduction

Summary

Table of Contents

Supplemental Materials