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Organic Chemistry

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Organic Chemistry Cover

 

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Publisher Comments:

Acclaimed for its clarity and precision, Wade’s Organic Chemistry maintains scientific rigor while engaging students at all levels. Wade presents a logical, systematic approach to understanding the principles of organic reactivity and the mechanisms of organic reactions. This approach helps students develop the problem-solving strategies and the scientific intuition they will apply throughout the course and in their future scientific work.

The Eighth Edition provides enhanced and proven features in every chapter, including new Chapter Goals, Essential Problem-Solving Skills and Hints that encourage both majors and non-majors to think critically and avoid taking "short cuts" to solve problems. Mechanism Boxes and Key Mechanism Boxes strengthen student understanding of Organic Chemistry as a whole while contemporary applications reinforce the relevance of this science to the real world.

 
NOTE: This is the standalone book Organic Chemistry,8/e if you want the book/access card order the ISBN below:
 

0321768140 / 9780321768148 Organic Chemistry Plus MasteringChemistry with eText — Access Card Package

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0321956273 / 9780321956279  ORG Organic Chemistry Plus MasteringChemistry with eText — Access Card Package & Get Ready for Organic Chemistry & Organic Molecular Model Kit & Solution Manual for Organic Chemistry, Books a la Carte Edition Package

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About the Author

L.G. “Skip” Wade decided to become a chemistry major during his sophomore year at Rice University, while taking organic chemistry from Professor Ronald M. Magid. After receiving his B.A. from Rice in 1969, Wade went on to Harvard University, where he did research with Professor James D. White. While at Harvard, he served as the Head Teaching Fellow for the organic laboratories and was strongly influenced by the teaching methods of two master educators, Professors Leonard K. Nash and Frank H. Westheimer.

After completing his Ph.D. at Harvard in 1974, Dr. Wade joined the chemistry faculty at Colorado State University. Over the course of fifteen years at Colorado State, Dr. Wade taught organic chemistry to thousands of students working toward careers in all areas of biology, chemistry, human medicine, veterinary medicine, and environmental studies. He also authored research papers in organic synthesis and in chemical education, as well as eleven books reviewing current research in organic synthesis. Since 1989, Dr. Wade has been a chemistry professor at Whitman College, where he teaches organic chemistry and pursues interests in organic synthesis and forensic chemistry. Dr. Wade received the A.E. Lange Award for Distinguished Science Teaching at Whitman in 1993.

Dr. Wade’s interest in forensic science has led him to testify as an expert witness in court cases involving drugs and firearms, and he has worked as a police firearms instructor, drug consultant, and boating safety officer. He also enjoys repairing and restoring old violins and bows, which he has done professionally for many years.

Table of Contents

Chapter 1: Introduction and Review

1.1 The Origins of Organic Chemistry

1.2 Principles of Atomic Structure

1.3 Bond Formation: The Octet Rule

1.4 Lewis Structures

1.5 Multiple Bonding

1.6 Electronegativity and Bond Polarity

1.7 Formal Charges

1.8 Ionic Structures

1.9 Resonance

1.10 Structural Formulas

1.11 Molecular Formulas and Empirical Formulas

1.12 Arrhenius Acids and Bases

1.13 Bronsted-Lowry Acids and Bases

1.14 Lewis Acids and Bases

Chapter 2: Structure and Properties of Organic Molecules

2.1 Wave Properties of Electrons in Orbitals

2.2 Molecular Orbitals

2.3 Pi Bonding

2.4 Hybridization and Molecular Shapes

2.5 Drawing Three-Dimensional Molecules

2.6 General Rules of Hybridization and Geometry

2.7 Bond Rotation

2.8 Isomerism

2.9 Polarity of Bonds and Molecules

2.10 Intermolecular Forces

2.11 Polarity Effects on Solubilities

2.12 Hydrocarbons

2.13 Organic Compounds Containing Oxygen

2.14 Organic Compounds Containing Nitrogen

Chapter 3: Structure and Stereochemistry of Alkanes

3.1 Classification of Hydrocarbons

3.2 Molecular Formulas of Alkanes

3.3 Nomenclature of Alkanes

3.4 Physical Properties of Alkanes

3.5 Uses and Sources of Alkanes

3.6 Reactions of Alkanes

3.7 Structure and Conformations of Alkanes

3.8 Conformations of Butane

3.9 Conformations of Higher Alkanes

3.10 Cycloalkanes

3.11 Cis-trans Isomerism in Cycloalkanes

3.12 Stabilities of Cycloalkanes; Ring Strain

3.13 Cyclohexane Conformations

3.14 Conformations of Monosubstituted Cyclohexanes

3.15 Conformations of Disubstituted Cyclohexanes

3.16 Bicyclic Molecules

Chapter 4: The Study of Chemical Reactions

4.1 Introduction

4.2 Chlorination of Methane

4.3 The Free-Radical Chain Reaction

4.4 Equilibrium Constants and Free Energy

4.5 Enthalpy and Entropy

4.6 Bond-Dissociation Enthalpies

4.7 Enthalpy Changes in Chlorination

4.8 Kinetics and the Rate Equation

4.9 Activation Energy and the Temperature Dependence of Rates

4.10 Transition States

4.11 Rates of Multistep Reactions

4.12 Temperature Dependence of Halogenation

4.13 Selectivity in Halogenation

4.14 The Hammond Postulate

4.15 Radical Inhibitors

4.16 Reactive Intermediates

Chapter 5: Stereochemistry

5.1 Introduction

5.2 Chirality

5.3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms

5.4 Optical Activity

5.5 Biological Discrimination of Enantiomers

5.6 Racemic Mixtures

5.7 Enantiomeric Excess and Optical Purity

5.8 Chirality of Conformationally Mobile Systems

5.9 Chiral Compounds without Asymmetric Atoms

5.10 Fischer Projections

5.11 Diastereomers

5.12 Stereochemistry of Molecules with Two or More Asymmetric Carbons

5.13 Meso Compounds

5.14 Absolute and Relative Configuration

5.15 Physical Properties of Diastereomers

5.16 Resolution of Enantiomers

Chapter 6: Alkyl Halides: Nucleophilic Substitution and Elimination

6.1 Introduction

6.2 Nomenclature of Alkyl Halides

6.3 Common Uses of Alkyl Halides

6.4 Structure of Alkyl Halides

6.5 Physical Properties of Alkyl Halides

6.6 Preparation of Alkyl Halides

6.7 Reactions of Alkyl Halides: Substitution and Elimination

6.8 Second-Order Nucleophilic Substitution: The SN2 Reaction

6.9 Generality of the SN2 Reaction

6.10 Factors Affecting SN2 Reactions: Strength of the Nucleophile

6.11 Reactivity of the Substrate in SN2 Reactions

6.12 Stereochemistry of the SN2 Reaction

6.13 First-Order Nucleophilic Substitution: the SN1 Reaction

6.14 Stereochemistry of the SN1 Reaction

6.15 Rearrangements in SN1 Reactions

6.16 Comparison of SN1 and SN2 Reactions

6.17 First-Order Elimination: The E1 Reaction

6.18 Positional Orientation of Elimination: Zaitsev's Rule

6.19 Second-Order Elimination: The E2 Reaction

6.20 Stereochemistry of the E2 Reaction

6.21 Comparison of E1 and E2 Elimination Mechanisms

Chapter 7: Structure and Synthesis of Alkenes

7.1 Introduction

7.2 The Orbital Description of the Alkene Double Bond

7.3 Elements of Unsaturation

7.4 Nomenclature of Alkenes

7.5 Nomenclature of Cis-Trans Isomers

7.6 Commercial Importance of Alkenes

7.7 Stability of Alkenes

7.8 Physical Properties of Alkenes

7.9 Alkene Synthesis by Elimination of Alkyl Halides

7.10 Alkene Synthesis by Dehydration of Alcohols

7.11 Alkene Synthesis by High-Temperature Industrial Methods

Chapter 8: Reactions of Alkenes

8.1 Reactivity of the Carbon-Carbon Double Bond

8.2 Electrophilic Addition to Alkenes

8.3 Addition of Hydrogen Halides to Alkenes

8.4 Addition of Water: Hydration of Alkenes

8.5 Hydration by Oxymercuration-Demercuration

8.6 Alkoxymercuration-Demercuration

8.7 Hydroboration of Alkenes

8.8 Addition of Halogens to Alkenes

8.9 Formation of Halohydrins

8.10 Catalytic Hydrogenation of Alkenes

8.11 Addition of Carbenes to Alkenes

8.12 Epoxidation of Alkenes

8.13 Acid-Catalyzed Opening of Epoxides

8.14 Syn Dihydroxylation of Alkenes

8.15 Oxidative Cleavage of Alkenes

8.16 Polymerization of Alkenes

8.17 Olefin Metathesis

Chapter 9: Alkynes

9.1 Introduction

9.2 Nomenclature of Alkynes

9.3 Physical Properties of Alkynes

9.4 Commercial Importance of Alkynes

9.5 Electronic Structure of Alkynes

9.6 Acidity of Alkynes; Formation of Acetylide Ions

9.7 Synthesis of Alkynes from Acetylides

9.8 Synthesis of Alkynes by Elimination Reactions

9.9 Addition of Reactions of Alkynes

9.10 Oxidation of Alkynes

Chapter 10: Structure and Synthesis of Alcohols

10.1 Introduction

10.2 Structure and Classification of Alcohols

10.3 Nomenclature of Alcohols and Phenols

10.4 Physical Properties of Alcohols

10.5 Commercially Important Alcohols

10.6 Acidity of Alcohols and Phenols

10.7 Synthesis of Alcohols: Introduction and Review

10.8 Organometallic Reagents for Alcohol Synthesis

10.9 Addition of Organometallic Reagents to Carbonyl Compounds

10.10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides

10.11 Reduction of the Carbonyl Group: Synthesis of 1º and 2º Alcohols

10.12 Thiols (Mercaptans)

Chapter 11: Reactions of Alcohols

11.1 Oxidation States of Alcohols and Related Functional Groups

11.2 Oxidation of Alcohols

11.3 Additional Methods for Oxidizing Alcohols

11.4 Biological Oxidation of Alcohols

11.5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates

11.6 Reduction of Alcohols

11.7 Reactions of Alcohols with Hydrohalic Acids

11.8 Reactions of Alcohols with Phosphorus Halides

11.9 Reactions of Alcohols with Thionyl Chloride

11.10 Dehydration Reactions of Alcohols

11.11 Unique Reactions of Diols

11.12 Esterification of Alcohols

11.13 Esters of Inorganic Acids

11.14 Reactions of Alkoxides

Chapter 12: Infrared Spectroscopy and Mass Spectrometry

12.1 Introduction

12.2 The Electromagnetic Spectrum

12.3 The Infrared Region

12.4 Molecular Vibrations

12.5 IR-Active and IR-Inactive Vibrations

12.6 Measurement of the IR Spectrum

12.7 Infrared Spectroscopy of Hydrocarbons

12.8 Characteristic Absorptions of Alcohols and Amines

12.9 Characteristic Absorptions of Carbonyl Compounds

12.10 Characteristic Absorptions of C-N Bonds

12.11 Simplified Summary of IR Stretching Frequencies

12.12 Reading and Interpreting IR Spectra (Solved Problems)

12.13 Introduction to Mass Spectrometry

12.14 Determination of the Molecular Formula by Mass Spectrometry

12.15 Fragmentation Patterns in Mass Spectrometry

Chapter 13: Nuclear Magnetic Resonance Spectroscopy

13.1 Introduction

13.2 Theory of Nuclear Magnetic Resonance

13.3 Magnetic Shielding by Electrons

13.4 The NMR Spectrometer

13.5 The Chemical Shift

13.6 The Number of Signals

13.7 Areas of the Peaks

13.8 Spin-Spin Splitting

13.9 Complex Splitting

13.10 Stereochemical Nonequivalence of Protons

13.11 Time Dependence of NMR Spectroscopy

13.12 Carbon-13 NMR Spectroscopy

13.13 Interpreting Carbon NMR Spectra

13.14 Nuclear Magnetic Resonance Imaging

Chapter 14: Ethers, Epoxides and Thioethers

14.1 Introduction

14.2 Physical Properties of Ethers

14.3 Nomenclature of Ethers

14.4 Spectroscopy of Ethers

14.5 The Williamson Ether Synthesis

14.6 Synthesis of Ethers by Alkoxymercuration-Demercuration

14.7 Industrial Synthesis: Bimolecular Condensation of Alcohols

14.8 Cleavage of Ethers by HBr and HI

14.9 Autoxidation of Ethers

14.10 Thioethers (Sulfides) and Silyl Ethers

14.11 Synthesis of Epoxides

14.12 Acid-Catalyzed Ring Opening of Epoxides

14.13 Base-Catalyzed Ring Opening of Epoxides

14.14 Orientation of Epoxide Ring Opening

14.15 Reactions of Epoxides with Grignard and Organolithium Reagents

14.16 Epoxy Resins: The Advent of Modern Glues

Chapter 15: Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

15.1 Introduction

15.2 Stabilities of Dienes

15.3 Molecular Orbital Picture of a Conjugated System

15.4 Allylic Cations

15.5 1,2 and 1,4 Addition to Conjugated Dienes

15.6 Kinetic versus Thermodynamic Control in the Addition of HBr

15.7 Allylic Radicals

15.8 Molecular Orbitals of the Allylic System

15.9 Electronic Configurations of the Allyl Radical, Cation and Anion

15.10 SN2 Displacement Reactions of Allylic Halides and Tosylates

15.11 The Diels-Alder Reaction

15.12 The Diels-Alder as an Example of a Pericyclic Reaction

15.13 Ultraviolet Absorption Spectroscopy

Chapter 16: Aromatic Compounds

16.1 Introduction: The Discovery of Benzene

16.2 The Structure and Properties of Benzene

16.3 The Molecular Orbitals of Benzene

16.4 The Molecular Orbital Picture of Cyclobutadiene

16.5 Aromatic, Antiaromatic, and Nonaromatic Compounds

16.6 Huckel's Rule

16.7 Molecular Orbital Derivation of Huckel's Rule

16.8 Aromatic Ions

16.9 Heterocyclic Aromatic Compounds

16.10 Polynuclear Aromatic Hydrocarbons

16.11 Aromatic Allotropes of Carbon

16.12 Fused Heterocyclic Compounds

16.13 Nomenclature of Benzene Derivatives

16.14 Physical Properties of Benzene and Its Derivatives

16.15 Spectroscopy of Aromatic Compounds

Chapter 17: Reactions of Aromatic Compounds

17.1 Electrophilic Aromatic Substitution

17.2 Halogenation of Benzene

17.3 Nitration of Benzene

17.4 Sulfonation of Benzene

17.5 Nitration of Toluene: The Effect of Alkyl Substitution

17.6 Activating, Ortho, Para-Directing Substituents

17.7 Deactivating, Meta-Directing Substituents

17.8 Halogen Substituents: Deactivating, but Ortho, Para-Directing

17.9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution

17.10 The Friedel-Crafts Alkylation

17.11 The Friedel-Crafts Acylation

17.12 Nucleophilic Aromatic Substitution

17.13 Aromatic Substitutions Using Organometallic Reagents (new section)

17.14 Addition Reactions of Benzene Derivatives

17.15 Side-Chain Reactions of Benzene Derivatives

17.16 Reactions of Phenols

Chapter 18: Ketones and Aldehydes

18.1 Carbonyl Compounds

18.2 Structure of the Carbonyl Group

18.3 Nomenclature of Ketones and Aldehydes

18.4 Physical Properties of Ketones and Aldehydes

18.5 Spectroscopy of Ketones and Aldehydes

18.6 Industrial Importance of Ketones and Aldehydes

18.7 Review of Syntheses of Ketones and Aldehydes

18.8 Synthesis of Ketones from Carboxylic Acids 18.9 Synthesis of Ketones and Aldehydes from Nitriles

18.10 Synthesis of Aldehydes and Ketones from Acid Chlorides and Esters

18.11 Reactions of Ketones and Aldehydes: Nucleophilic Addition

18.12 The Wittig Reaction

18.13 Hydration of Ketones and Aldehydes

18.14 Formation of Cyanohydrins

18.15 Formation of Imines

18.16 Condensations with Hydroxylamine and Hydrazines

18.17 Formation of Acetals

18.18 Use of Acetals as Protecting Groups

18.19 Oxidation of Aldehydes

18.20 Reductions of Ketones and Aldehydes

Chapter 19: Amines

19.1 Introduction

19.2 Nomenclature of Amines

19.3 Structure of Amines

19.4 Physical Properties of Amines

19.5 Basicity of Amines

19.6 Effects on Amine Basicity

19.7 Salts of Amines

19.8 Spectroscopy of Amines

19.9 Reactions of Amines with Ketones and Aldehydes (Review)

19.10 Aromatic Substitution of Arylamines and Pyridine

19.11 Alkylation of Amines by Alkyl Halides

19.12 Acylation of Amines by Acid Chlorides

19.13 Formation of Sulfonamides

19.14 Amines as Leaving Groups: The Hofmann Elimination

19.15 Oxidation of Amines; The Cope Elimination

19.16 Reactions of Amines with Nitrous Acid

19.17 Reactions of Arenediazonium Salts

19.18 Synthesis of Amines by Reductive Amination

19.19 Synthesis of Amines by Acylation-Reduction

19.20 Syntheses Limited to Primary Amines

Chapter 20: Carboxylic Acids

20.1 Introduction

20.2 Nomenclature of Carboxylic Acids

20.3 Structure and Physical Properties of Carboxylic Acids

20.4 Acidity of Carboxylic Acids

20.5 Salts of Carboxylic Acids

20.6 Commercial Sources of Carboxylic Acids

20.7 Spectroscopy of Carboxylic Acids

20.8 Synthesis of Carboxylic Acids

20.9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution

20.10 Condensation of Acids with Alcohols: The Fischer Esterification

20.11 Esterification Using Diazomethane

20.12 Condensation of Acids with Amines: Direct Synthesis of Amides

20.13 Reduction of Carboxylic Acids

20.14 Alkylation of Carboxylic Acids to Form Ketones

20.15 Synthesis and Use of Acid Chlorides

Chapter 21: Carboxylic Acid Derivatives

21.1 Introduction

21.2 Structure and Nomenclature of Acid Derivatives

21.3 Physical Properties of Carboxylic Acid Derivatives

21.4 Spectroscopy of Carboxylic Acid Derivatives

21.5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution

21.6 Transesterification

21.7 Hydrolysis of Carboxylic Acid Derivatives

21.8 Reduction of Acid Derivatives

21.9 Reactions of Acid Derivatives with Organometallic Reagents

21.10 Summary of the Chemistry of Acid Chlorides

21.11 Summary of the Chemistry of Anhydrides

21.12 Summary of the Chemistry of Esters

21.13 Summary of the Chemistry of Amides

21.14 Summary of the Chemistry of Nitriles

21.15 Thioesters

21.16 Esters and Amides of Carbonic Acid

Chapter 22: Condensations and Alpha Substitutions of Carbonyl Compounds

22.1 Introduction

22.2 Enols and Enolate Ions

22.3 Alkylation of Enolate Ions

22.4 Formation and Alkylation of Enamines

22.5 Alpha Halogenation of Ketones

22.6 Bromination of Acids: The HVZ Reaction

22.7 The Aldol Condensation of Ketones and Aldehydes

22.8 Dehydration of Aldol Products

22.9 Crossed Aldol Condensations

22.10 Aldol Cyclizations

22.11 Planning Syntheses Using Aldol Condensations

22.12 The Claisen Ester Condensation

22.13 The Dieckmann Condensation: A Claisen Cyclization

22.14 Crossed Claisen Condensations

22.15 Syntheses Using β-Dicarbonyl Compounds

22.16 The Malonic Ester Synthesis

22.17 The Acetoacetic Ester Synthesis

22.18 Conjugate Additions: The Michael Reaction

22.19 The Robinson Annulation

Chapter 23: Carbohydrates and Nucleic Acids

23.1 Introduction

23.2 Classification of Carbohydrates

23.3 Monosaccharides

23.4 Erythro and Threo Diastereomers

23.5 Epimers

23.6 Cyclic Structures of Monosaccharides

23.7 Anomers of Monosaccharides; Mutarotation

23.8 Reactions of Monosaccharides: Side Reactions in Base

23.9 Reduction of Monosaccharides

23.10 Oxidation of Monosaccharides; Reducing Sugars

23.11 Nonreducing Sugars: Formation of Glycosides

23.12 Ether and Ester Formation

23.13 Reactions with Phenylhydrazine: Osazone Formation

23.14 Chain Shortening: The Ruff Degradation

23.15 Chain Lengthening: The Kiliani-Fischer Synthesis

23.16 Determination of Ring Size; Periodic Acid Cleavage of Sugars

23.17 Disaccharides

23.18 Polysaccharides

23.19 Nucleic Acids: Introduction

23.20 Ribonucleosides and Ribonucleotides

23.21 The Structure of RNA and DNA

23.22 Additional Functions of Nucleotides

Chapter 24: Amino Acids, Peptides, and Proteins

24.1 Introduction

24.2 Structure and Stereochemistry of the Amino Acids

24.3 Acid-Base Properties of Amino Acids

24.4 Isoelectric Points and Electrophoresis

24.5 Synthesis of Amino Acids

24.6 Resolution of Amino Acids

24.7 Reactions of Amino Acids

24.8 Structure and Nomenclature of Peptides and Proteins

24.9 Peptide Structure Determination

24.10 Solution-Phase Peptide Synthesis

24.11 Solid-Phase Peptide Synthesis

24.12 Classification of Proteins

24.13 Levels of Protein Structure

24.14 Protein Denaturation

Chapter 25: Lipids

25.1 Introduction

25.2 Waxes

25.3 Trigylcerides

25.4 Saponification of Fats and Oils; Soaps and Detergents

25.5 Phospholipids

25.6 Steroids

25.7 Prostaglandins

25.8 Terpenes

Chapter 26:

26.1 Introduction

26.2 Addition Polymers

26.3 Stereochemistry of Polymers

26.4 Stereochemical Control of Polymerization; Ziegler-Natta Catalysts

26.5 Natural and Synthetic Rubbers

26.6 Copolymers of Two or More Monomers

26.7 Condensation Polymers

26.8 Polymer Structure and Properties

Product Details

ISBN:
9780321768414
Author:
Wade, L. G., Jr.
Publisher:
Prentice Hall
Author:
Wade, Leroy G. Jr.
Author:
Wade, L. G.
Author:
Simek, Jan W.
Subject:
Chemistry - Organic
Copyright:
Publication Date:
20120101
Binding:
HARDCOVER
Language:
English
Pages:
1320
Dimensions:
11 x 8.8 x 1.8 in 2867 gr

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0321956273 / 9780321956279  ORG Organic Chemistry Plus MasteringChemistry with eText — Access Card Package & Get Ready for Organic Chemistry & Organic Molecular Model Kit & Solution Manual for Organic Chemistry, Books a la Carte Edition Package

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