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Organic Chemistry + 1pass for Organic ChemistryNOW: A Biological Approach

by: McMurry, John E.

Organic Chemistry + 1pass for Organic ChemistryNOW: A Biological Approach

by: McMurry, John E.

ISBN 13:
9780495015253
ISBN 10:
0495015253
Edition: 1st
Format: Hardcover
Copyright: 03/28/2006
Publisher: Brooks Cole
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Summary

Renowned for his student-friendly writing style, John McMurry introduces a new way to teach organic chemistry: ORGANIC CHEMISTRY: A BIOLOGICAL APPROACH. Traditional foundations of organic chemistry are enhanced by a consistent integration of biological examples and discussion of the organic chemistry of biological pathways. This innovative text is coupled with media integration through Organic ChemistryNow and Organic OWL, providing instructors and students the tools they need to succeed.

Structure and Bonding

(34)

Atomic Structure: The Nucleus

(1)

Atomic Structure: Orbitals

(1)

Atomic Structure: Electron Configurations

(1)

Development of Chemical Bonding Theory

(4)

The Nature of Chemical Bonds: Valence Bond Theory

(1)

sp3 Hybrid Orbitals and the Structure of Methane

(2)

sp3 Hybrid Orbitals and the Structure of Ethane

(1)

sp2 Hybrid Orbitals and the Structure of Ethylene

(3)

sp Hybrid Orbitals and the Structure of Acetylene

(2)

Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur

(2)

The Nature of Chemical Bonds: Molecular Orbital Theory

(1)

Drawing Chemical Structures

(13)

Lagniappe: Chemicals, Toxicity, and Risk

(1)

Summary

(2)

Exercises

(7)

Polar Covalent Bonds: Acids and Bases

(40)

Polar Covalent Bonds: Electronegativity

(3)

Polar Covalent Bonds: Dipole Moments

(2)

Formal Charges

(3)

Resonance

(2)

Rules for Resonance Forms

(2)

Drawing Resonance Forms

(3)

Acids and Bases: The Bronsted-Lowry Definition

(1)

Acid and Base Strength

(2)

Predicting Acid-Base Reactions from pKa Values

(2)

Organic Acids and Organic Bases

(3)

Acids and Bases: The Lewis Definition

(4)

Noncovalent Interactions between Molecules

(13)

Lagniappe: Alkaloids: Naturally Occurring Bases

(1)

Summary

(1)

Exercises

(8)

Organic Compounds: Alkanes and Their Stereochemistry

(36)

Functional Groups

(7)

Alkanes and Alkane Isomers

(4)

Alkyl Groups

(3)

Naming Alkanes

(6)

Properties of Alkanes

(1)

Conformations of Ethane

(2)

Conformations of Other Alkanes

(13)

Lagniappe: Gasoline

103

(1)

Summary

104

(1)

Exercises

104

(7)

Organic Compounds: Cycloalkanes and Their Stereochemistry

111

(30)

Naming Cycloalkanes

112

(3)

Cis-Trans Isomerism in Cycloalkanes

115

(3)

Stability of Cycloalkanes: Ring Strain

118

(1)

Conformations of Cycloalkanes

119

(2)

Conformations of Cyclohexane

121

(2)

Axial and Equatorial Bonds in Cyclohexane

123

(3)

Conformations of Monosubstituted Cyclohexanes

126

(2)

Conformations of Disubstituted Cyclohexanes

128

(3)

Conformations of Polycyclic Molecules

131

(10)

Lagniappe: Molecular Mechanics

133

(1)

Summary

133

(1)

Exercises

134

(7)

An Overview of Organic Reactions

141

(38)

Kinds of Organic Reactions

141

(2)

How Organic Reactions Occur: Mechanisms

143

(1)

Radical Reactions

144

(3)

Polar Reactions

147

(4)

An Example of a Polar Reaction: Addition of H2O to Ethylene

151

(3)

Using Curved Arrows in Polar Reaction Mechanisms

154

(3)

Describing a Reaction: Equilibria. Rates, and Energy Changes

157

(4)

Describing a Reaction: Bond Dissociation Energies

161

(2)

Describing a Reaction: Energy Diagrams and Transition States

163

(3)

Describing a Reaction: Intermediates

166

(2)

A Comparison between Biological Reactions and Laboratory Reactions

168

(11)

Lagniappe: Where Do Drugs Come From?

171

(1)

Summary

172

(1)

Exercises

173

(6)

Alkenes and Alkynes

179

(42)

Calculating a Degree of Unsaturation

180

(2)

Naming Alkenes and Alkynes

182

(3)

Cis-Trans Isomerism in Alkenes

185

(2)

Sequence Rules: The EZ Designation

187

(5)

Stability of Alkenes

192

(3)

Electrophilic Addition Reactions of Alkenes

195

(3)

Orientation of Electrophilic Addition: Markovnikov's Rule

198

(3)

Carbocation Structure and Stability

201

(3)

The Hammond Postulate

204

(2)

Carbocation Rearrangements

206

(15)

Lagniappe: Terpenes: Naturally Occurring Alkenes

209

(1)

Summary

210

(1)

Exercises

211

(10)

Reactions of Alkenes and Alkynes

221

(46)

Preparation of Alkenes: A Preview of Elimination Reactions

222

(2)

Halogenation of Alkenes

224

(2)

Halohydrins from Alkenes

226

(1)

Hydration of Alkenes

227

(5)

Reduction of Alkenes

232

(3)

Oxidation of Alkenes: Epoxidation

235

(1)

Oxidation of Alkenes: Hydroxylation

236

(3)

Radical Additions to Alkenes: Alkene Polymers

239

(4)

Biological Additions of Radicals to Alkenes

243

(1)

Conjugated Dienes

244

(4)

Reactions of Conjugated Dienes

248

(3)

Reactions of Alkynes

251

(16)

Lagniappe: Natural Rubber

253

(1)

Summary

254

(1)

Summary of Reactions

255

(3)

Exercises

258

(9)

Aromatic Compounds

267

(52)

Structure and Stability of Benzene

270

(3)

Aromaticity and the Huckel 4n + 2 Rule

273

(2)

Aromatic Heterocycles

275

(3)

Polycyclic Aromatic Compounds

278

(3)

Reactions of Aromatic Compounds: Electrophilic Substitution

281

(7)

Alkylation and Acylation of Aromatic Rings

288

(4)

Substituent Effects in Electrophilic Substitutions

292

(6)

Oxidation and Reduction of Aromatic Compounds

298

(2)

An Introduction to Organic Synthesis: Polysubstituted Benzenes

300

(19)

Lagniappe: Combinatorial Chemistry

306

(1)

Summary

307

(1)

Summary of Reactions

308

(2)

Exercises

310

(9)

Stereochemistry

319

(136)

Enantiomers and the Tetrahedral Carbon

320

(1)

The Reason for Handedness in Molecules: Chirality

321

(4)

Optical Activity

325

(2)

Pasteur's Discovery of Enantiomers

327

(1)

Sequence Rules for Specifying Configuration

328

(5)

Diastereomers

333

(2)

Meso Compounds

335

(3)

Racemates and the Resolution of Enantiomers

338

(2)

A Brief Review of Isomerism

340

(2)

Stereochemistry of Reactions: Addition of H2O to an Achiral Alkene

342

(1)

Stereochemistry of Reactions: Addition of H2O to a Chiral Alkene

343

(2)

Chirality at Nitrogen, Phosphorus, and Sulfur

345

(1)

Prochirality

346

(3)

Chirality in Nature

349

(106)

Lagniappe: Chiral Drugs

351

(1)

Summary

352

(1)

Exercises

353

(102)

Structure Determination: Nuclear Magnetic Resonance Spectroscopy

455

(42)

Nuclear Magnetic Resonance Spectroscopy

455

(2)

The Nature of NMR Absorptions

457

(3)

Chemical Shifts

460

(2)

13C NMR Spectroscopy: Signal Averaging and FT-NMR

462

(2)

Characteristics of 13C NMR Spectroscopy

464

(3)

DEPT 13C NMR Spectroscopy

467

(2)

Uses of 13C NMR Spectroscopy

469

(1)

1H NMR Spectroscopy and Proton Equivalence

470

(3)

Chemical Shifts in 1H NMR Spectroscopy

473

(2)

Integration of 1H NMR Absorptions: Proton Counting

475

(1)

Spin-Spin Splitting in 1H NMR Spectra

476

(6)

More Complex Spin-Spin Splitting Patterns

482

(2)

Uses of 1H NMR Spectroscopy

484

(13)

Lagniappe: Magnetic Resonance Imaging (MRI)

485

(1)

Summary

485

(1)

Exercises

486

(11)

Alcohols, Phenols, and Thiols; Ethers and Sulfides

497

(50)

Naming Alcohols, Phenols, and Thiols

499

(2)

Properties of Alcohols, Phenols, and Thiols

501

(3)

Preparation of Alcohols from Carbonyl Compounds

504

(8)

Reactions of Alcohols

512

(4)

Oxidation of Alcohols and Phenols

516

(4)

Preparation and Reactions of Thiols

520

(2)

Ethers and Sulfides

522

(1)

Preparation of Ethers

523

(2)

Reactions of Ethers

525

(2)

Preparation and Reactions of Sulfides

527

(2)

Spectroscopy of Alcohols, Phenols, and Ethers

529

(18)

Lagniappe: Ethanol: Chemical, Drug, and Poison

532

(1)

Summary

532

(1)

Summary of Reactions

533

(3)

Exercises

536

(11)

A Preview of Carbonyl Chemistry

547

Kinds of Carbonyl Compounds

547

Nature of the Carbonyl Group

549

General Reactions of Carbonyl Compounds

550

Summary

555

Aldehydes and Ketones: Nucleophilic Addition Reactions

557

Naming Aldehydes and Ketones

558

Preparation of Aldehydes and Ketones

560

Oxidation of Aldehydes

561

Nucleophilic Addition Reactions of Aldehydes and Ketones

562

Nucleophilic Addition of H2O: Hydration

564

Nucleophilic Addition of Grignard and Hydride Reagents: Alcohol Formation

567

Nucleophilic Addition of Amines: Imine and Enamine Formation

568

Nucleophilic Addition of Alcohols: Acetal Formation

572

Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction

575

Biological Reductions

579

Conjugate Nucleophilic Addition to a, b-Unsaturated Aldehydes and Ketones

580

Spectroscopy of Aldehydes and Ketones

583

Lagniappe: Enantioselective Synthesis

587

Summary

588

Summary of Reactions

588

Exercises

590

Carboxylic Acids and Nitriles

601

Naming Carboxylic Acids and Nitriles

602

Structure and Properties of Carboxylic Acids

605

Biological Acids and the Henderson-Hasselbalch Equation

608

Substituent Effects on Acidity

609

Preparation of Carboxylic Acids

611

Reactions of Carboxylic Acids: An Overview

613

Chemistry of Nitriles

614

Spectroscopy of Carboxylic Acids and Nitriles

617

Lagniappe: Vitamin C

618

Summary

620

Summary of Reactions

620

Exercises

622

Amines and Heterocycles

735

Naming Amines

736

Properties of Amines

739

Basicity of Amines

740

Basicity of Arylamines

743

Biological Amines and the Henderson-Hasselbalch Equation

745

Synthesis of Amines

746

Reactions of Amines

751

Heterocyclic Amines

755

Fused-Ring Heterocycles

759

Spectroscopy of Amines

762

Lagniappe: Green Chemistry

764

Summary

765

Summary of Reactions

766

Exercises

768

Biomolecules: Amino Acids, Peptides, and Proteins

777

Structures of Amino Acids

778

Isoelectric Points

783

Synthesis of Amino Acids

784

Peptides and Proteins

787

Amino Acid Analysis of Peptides

789

Peptide Sequencing: The Edman Degradation

790

Peptide Synthesis

792

Protein Structure

797

Enzymes and Coenzymes

800

How Do Enzymes Work? Citrate Synthase

804

Lagniappe: The Protein Data Bank

807

Summary

808

Summary of Reactions

809

Exercises

810

Amino Acid Metabolism

817

An Overview of Metabolism and Biochemical Energy

818

Catabolism of Amino Acids: Deamination

822

The Urea Cycle

827

Catabolism of Amino Acids: The Carbon Chains

831

Biosynthesis of Amino Acids

838

Lagniappe: Visualizing Enzyme Structures

844

Summary

845

Exercises

846

Biomolecules: Carbohydrates

851

Classification of Carbohydrates

852

Depicting Carbohydrate Stereochemistry: Fischer Projections

853

D.L Sugars

858

Configurations of the Aldoses

859

Cyclic Structures of Monosaccharides: Anomers

862

Reactions of Monosaccharides

866

The Eight Essential Monosaccharides

872

Disaccharides

873

Polysaccharides and Their Synthesis

876

Cell-Surface Carbohydrates and Carbohydrate Vaccines

879

Lagniappe: Sweetness

880

Summary

881

Exercises

882

Carbohydrate Metabolism

891

Hydrolysis of Complex Carbohydrates

892

Catabolism of Glucose: Glycolysis

893

Conversion of Pyruvate to Acetyl CoA

901

The Citric Acid Cycle

905

Biosynthesis of Glucose: Gluconeogenesis

912

Lagniappe: Avian Flu

920

Summary

921

Exercises

921

Biomolecules: Lipids and Their Metabolism

927

Waxes, Fats, and Oils

928

Soap

931

Phospholipids

933

Catabolism of Triacylglycerols: The Fate of Glycerol

934

Catabolism of Triacylglycerols: b-Oxidation

937

Biosynthesis of Fatty Acids

943

Prostaglandins and Other Eicosanoids

948

Terpenoids

950

Amazon no longer offers textbook rentals. We do!

Organic Chemistry + 1pass for Organic ChemistryNOW: A Biological Approach

Organic Chemistry + 1pass for Organic ChemistryNOW: A Biological Approach

9780495015253

0495015253

Summary

Table of Contents

Supplemental Materials

Write a Review

Amazon no longer offers textbook rentals. We do!

Organic Chemistry + 1pass for Organic ChemistryNOW: A Biological Approach

Organic Chemistry + 1pass for Organic ChemistryNOW: A Biological Approach

9780495015253

0495015253

Summary

Table of Contents

Supplemental Materials

Write a Review

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