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Organic Chemistry / With CD-ROM

Organic Chemistry / With CD-ROM - 4th edition

Organic Chemistry / With CD-ROM - 4th edition

ISBN13: 9780195119992

ISBN10: 0195119991

Organic Chemistry / With CD-ROM by Marc G. Loudon - ISBN 9780195119992
Edition: 4TH 02
Copyright: 2002
Publisher: Oxford University Press
International: No
Organic Chemistry / With CD-ROM by Marc G. Loudon - ISBN 9780195119992

ISBN13: 9780195119992

ISBN10: 0195119991

Edition: 4TH 02

Other Editions of Organic Chemistry / With CD-ROM

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With a reputation for outstanding scientific quality, Organic Chemistry by G. Marc Loudon is a textbook that students will actually want to read. This much-anticipated fourth edition continues its predecessors' popular and unique mechanistic approach within a functional group framework. Enhanced biological and biochemical material make it ideal for chemistry majors as well as premedical and prepharmacy students taking a full-year, sophomore level course. Loudon's excellent use of language and reader-friendly style transform organic chemistry into a logical, understandable, and exciting subject for students. In use at undergraduate and graduate schools of all levels, this authoritative yet accessible volume is packed with effective analogies that enliven and clarify rigorous discussions of important concepts. For example, Loudon uses a flute player jumping between musical octaves to explain transitions between quantum levels. An engaging detective with combined characteristics from Sherlock Holmes and James Bond depicts resonance structures. Thanks to humorous characters like Flick Flaskflinger and Professor Havno Scentz, problem solving becomes simultaneously challenging and entertaining. Varying from the routine to the complex, Loudon's problems are renowned for their originality, their range of difficulty levels, and their ability to teach students to understand and predict organic reactivity rather than just memorize facts. In addition, Loudon blends biological, environmental, and industrial applications of organic chemistry into the body of the text--rather than separating them as "special topics"--giving students an integrated sense of the subject in its real-life context.

Table of Contents

Table of Contents

Chapter 1. Chemical Bonding and Chemical Structure

1.1. Introduction
1.2. Classical Theories of Chemical Bonding
1.3. Structures of Covalent Compounds
1.4. Resonance Structures
1.5. Wave Nature of the Electron
1.6. Electronic Structure of the Hydrogen Atom
1.7. Electronic Structures of More Complex Atoms
1.8. Another Look at the Covalent Bond: Molecular Orbitals
1.9. Hybrid Orbitals

Chapter 2. Alkanes

2.1. Hydrocarbons
2.2. Unbranched Alkanes
2.3. Conformations of Alkanes
2.4. Constitutional Isomers and Nomenclature
2.5. Cycloalkanes and Skeletal Structures
2.6. Physical Properties of Alkanes
2.7. Combustion and Elemental Analysis
2.8. Occurrence and Use of Alkanes
2.9. Functional Groups, Compound Classes, and "R" Notation

Chapter 3. Acids and Bases: The Curved-Arrow Notation

3.1. Lewis Acid-Base Association Reactions
3.2. Electron-Pair Displacement Reactions
3.3. Review of the Curved-Arrow Notation
3.4. Bronsted-Lowry Acids and Bases
3.5. Free Energy and Chemical Equilibrium
3.6. Relationship of Structure to Acidity

Chapter 4. Introduction to Alkenes: Structure and Reactivity

4.1. Structure and Bonding in Alkenes
4.2. Nomenclature of Alkenes
4.3. Unsaturation Number
4.4. Physical Properties of Alkenes
4.5. Relative Stabilities of Alkene Isomers
4.6. Addition Reactions of Alkenes
4.7. Addition of Hydrogen Halides to Alkenes
4.8. Reaction Rates
4.9. Catalysis

Chapter 5. Addition Reactions of Alkenes

5.1. Reactions of Alkenes with Halogens
5.2. Writing Organic Reactions
5.3. Conversion of Alkenes into Alcohols
5.4. Ozonolysis of Alkenes
5.5. Conversion of Alkenes into Glycols
5.6. Free-Radical Addition of Hydrogen Bromide to Alkenes
5.7. Polumers: Free-Radical Polymerization of Alkenes
5.8. Alkenes in the Chemical Industry

Chapter 6. Principles of Stereochemistry

6.1. Enantiomers, Chirality, and Symmetry
6.2. Nomenclature of Enantiomers: The R,S System
6.3. Physical Properties of Enantiomers: Optical Activity
6.4. Racemates
6.5. Stereochemical Correlation
6.6. Diastereomers
6.7. Meso Compounds
6.8. Enantiomeric Resolution
6.9. Chiral Molecules without Asymmetric Atoms
6.10. Conformational Stereoisomers
6.11. Fischer Projections

Chapter 7. Cyclic Compounds: Stereochemistry of Reactions

7.1. Relative Stabilities of the Monocyclic Alkanes
7.2. Conformations of Cyclohexane
7.3. Monosubstituted Cyclohexanes: Conformational Analysis
7.4. Disubstituted Cyclohexanes
7.5. Cyclopentane, Cyclobutane, and Cyclopropane
7.6. Bicyclic and Polycyclic Compounds
7.7. Relative Reactivities of Stereoisomers
7.8. Reactions that Form Stereoisomers
7.9. Stereochemistry of Chemical Reactions

Chapter 8. Introduction to Alkyl Halides, Alcohols, Ethers, Thiols, and Sulfides

8.1. Nomenclature
8.2. Structures
8.3. Effect of Molecular Polarity and Hydrogen Bonding on Physical Properties
8.4. Solvents in Organic Chemistry
8.5. Applications of Solubility and Solvation Principles
8.6. Acidity of Alcohols and Thiols
8.7. Basicity of Alcohols and Ethers
8.8. Grignard and Organolithium Reagents
8.9. Industrial Preparation and Use of Alkyl Halides, Alcohols, and Ethers

Chapter 9. Chemsitry of Alkyl Halides

9.1. An Overview of Nucleophilic Substitution and beta-Elimination Reactions
9.2. Equilibrium in Nucleophilic Substitution Reactions
9.3. Reaction Rates
9.4. The SN2 Reaction
9.5. The E2 Reaction
9.6. The SN1 and E1 Reactions
9.7. Summary of Substitution and Elimination Reactions of Alkyl Halides
9.8. Carbenes and Carbenoids

Chapter 10. Chemistry of Alcohols and Thiols

10.1. Dehydration of Alcohols
10.2. Reactions of Alcohols with Hydrogen Halides
10.3. Sulfonate and Inorganic Ester Derivatives of Alcohols
10.4. Conversion of Alcohols into Alkyl Halides: Summary
10.5. Oxidation and Reduction in Organic Chemistry
10.6. Oxidation of Alcohols
10.7. Biological Oxidation of Ethanol
10.8. Chemical and Stereochemical Group Equivalence
10.9. Oxidation of Thiols
10.10. Synthesis of Alcohols and Glycols
10.11. Design of Organic Synthesis

Chapter 11. Chemistry of Ethers, Epoxides, and Sulfides

11.1. Synthesis of Ethers and Sulfides
11.2. Synthesis of Epoxides
11.3. Cleavage of Ethers
11.4. Nucleophilic Substitution Reactions of Epoxides
11.5. Oxonium and Sulfonium Salts
11.6. Neighboring-Group Participation: Intramolecular Reactions
11.7. Oxidation of Ethers and Sulfides
11.8. The Three Fundamental Operations of Organic Synthesis

Chapter 12. Introduction to Spectroscopy: Infrared Spectroscopy and Mass Spectrometry

12.1. Introduction to Spectroscopy
12.2. Infrared Spectroscopy
12.3. Infrared Absorption and Chemical Structure
12.4. Functional-Group Infrared Absorptions
12.5. The Infrared Spectrometer
12.6. Introduction to Mass Spectrometry

Chapter 13. Nuclear Magnetic Resonance Spectroscopy

13.1. An Overview of Proton NMR Spectroscopy
13.2. Physical Basis of NMR Spectroscopy
13.3. The NMR Spectrum: Chemical Shift and Integral
13.4. The NMR Spectrum: Spin-Spin Splitting
13.5. Complex NMR Spectra
13.6. Use of Deuterium in Proton NMR
13.7. Characteristic Functional-Group NMR Absorptions
13.8. NMR Spectroscopy of Dynamic Systems
13.9. Carbon NMR
13.10. Solving Structure Problems with Spectroscopy
13.11. The NMR Spectrometer
13.12. Other Uses of NMR

Chapter 14. Chemistry of Alkynes

14.1. Nomenclature of Alkynes
14.2. Structure and Bonding in Alkynes
14.3. Physical Properties of Alkynes
14.4. Introduction to Addition Reactions of the Triple Bond
14.5. Conversion of Alkynes into Aldehydes and Ketones
14.6. Reduction of Alkynes
14.7. Acidity of 1-Alkynes
14.8. Organic Synthesis Using Alkynes
14.9. Pheromones
14.10. Occurrence and Use of Alkynes

Chapter 15. Dienes, Resonance, and Aromaticity

15.1. Structure and Stability of Dienes
15.2. Ultraviolet Spectroscopy
15.3. The Diels-Alder Reaction
15.4. Addition of Hydrogen Halides to Conjugated Dienes
15.5. Diene Polymers
15.6. Resonance
15.7. Introduction to Aromatic Compounds

Chapter 16. Chemistry of Benzene and Its Derivatives

16.1. Nomenclature of Benzene Derivatives
16.2. Phsyical Properties of Benzene Derivatives
16.3. Spectroscopy of Benzene Derivatives
16.4. Elctrophilic Aromatic Substitution Reactions of Benzene
16.5. Electrophilic Aromatic Substitution Reactions of Subtituted Benzenes
16.6. Hydrogenation of Benzene Derivatives
16.7. Source and Industrial Use of Aromatic Hydrocarbons

Chapter 17. Allylic and Benzylic Reactivity

17.1. Reactions Involving Allylic and Benzylic Carbocations
17.2. Reactions Involving Allylic and Benzylic Radicals
17.3. Reactions Involving Allylic and Benzylic Anions
17.4. Allylic and Benzylic SN2 Reactions
17.5. Benzylic Oxidation of Alkylbenzenes
17.6. Terpenes

Key Ideas in Chapter 17
Additional Problems

Chapter 18. The Chemistry of Aryl Halides, Vinylic Halides, and Phenols: Transition-Metal Catalysis

18.1. Lack of Reactivity of Vinylic and Aryl Halides under SN2 Conditions
18.2. Elimination Reactions of Vinylic Halides
18.3. Lack of Reactivity of Vinylic and Aryl Halides under SN1 Conditions
18.4. Nucleophilic Substitution Reactions of Aryl Halides
18.5. Transition-Metal Catalyzed Coupling Reactions
18.6. Acidity of Phenols
18.7. Oxidation of Phenols to Quinones
18.8. Electrophilic Aromatic Substitution Reactions of Phenols
18.9. Reactivity of the Aryl-Oxygen Bond
18.10. Industrial Preparation and Use of Phenol

Chapter 19. The Chemistry of Aldehydes and Ketones: Carbonyl-Addition Reactions

19.1. Nomenclature of Aldehydes and Ketones
19.2. Physical Properties of Aldehydes and Ketones
19.3. Spectroscopy of Aldehydes and Ketones
19.4. Synthesis of Aldehydes and Ketones
19.5. Introduction to Aldehyde and Ketone Reactions
19.6. Basicity of Aldehydes and Ketones
19.7. Reversible Addition Reactions of Aldehydes and Ketones
19.8. Reduction of Aldehydes and Ketones to Alcohols
19.9. Reactions of Aldehydes and Ketones with Grignard and Related Reagents
19.10. Acetals and Their Use as Protecting Groups
19.11. Reactions of Aldehydes and Ketones with Amines
19.12. Reduction of Carbonyl Groups to Methylene Groups
19.13. The Wittig Alkene Synthesis
19.14. Oxidation of Aldehydes to Carboxylic Acids
19.15. Manufacture and Use of Aldehydes and Ketones

Chapter 20. Chemistry of Carboxylic Acids

20.1. Nomenclature of Carboxylic Acids
20.2. Structure and Physical Properties of Carboxylic Acids
20.3. Spectroscopy of Carboxylic Acids
20.4. Acid-Base Properties of Carboxylic Acids
20.5. Fatty Acids, Soaps, and Detergents
20.6. Synthesis of Carboxylic Acid Reactions
20.7. Introduction to Carboxylic Acid Reactions
20.8. Conversion of Carboxylic Acids into Esters
20.9. Conversion of Carboxylic Acids into Acid Chlorides and Anhydrides
20.10. Reduction of Carboxylic Acids to Primary Alcohols
20.11. Decarboxylation of Carboxylic Acids

Chapter 21. Chemistry of Carboxylic Acid Derivatives

21.1. Nomenclature and Classification of Carboxylic Acid Derivatives
21.2. Structures of Carboxylic Acid Derivatives
21.3. Physical Properties of Carboxylic Acid Derivatives
21.4. Spectroscopy of Carboxylic Acid Derivatives
21.5. Basicity of Carboxylic Acid Derivatives
21.6. Introduction to Reactions of Carboxylic Acid Derivatives
21.7. Hydrolysis of Carboxylic Acid Derivatives
21.8. Reactions of Carboxylic Acid Derivatives with Nucleophiles
21.9. Reduction of Carboxylic Acid Derivatives
21.10. Reactions of Carboxylic Acid Derivatives with Organometallic Reagents
21.11. Synthesis of Carboxylic Acid Derivatives
21.12. Use and Occurrence of Carboxylic Acids and Their Derivatives

Chapter 22. Chemistry of Enolate Ions, Enols, and alpha,beta-Unsaturated Carbonyl Compounds

22.1. Acidity of Carbonyl Compounds
22.2. Enolization of Carbonyl Compounds
22.3. alpha-Halogenation of Carbonyl Compounds
22.4. Aldol Addition and Aldol Condensation
22.5. Condensation Reactions Involving Ester Enolate Ions
22.6. Biosynthesis of Fatty Acids
22.7. Alkylation of Ester Enolate Ions
22.8. Conjugate-Addition Reactions
22.9. Reduction of alpha,beta-Unsaturated Carbonyl Compounds
22.10. Reactions of alpha,beta-Unsaturated Carbonyl Compounds with Organometallic Reagents
22.11. Organic Synthesis with Conjugate-Addition Reactions

Chapter 23. Chemistry of Amines

23.1. Nomenclature of Amines
23.2. Structure of Amines
23.3. Physical Properties of Amines
23.4. Spectroscopy of Amines
23.5. Basicity and Acidity of Amines
23.6. Quaternary Ammonium Salts
23.7. Alkylation and Acylation Reactions of Amines
23.8. Hofmann Elimination of Quaternary Ammonium Hydroxides
23.9. Aromatic Substitution Reactions of Aniline Derivatives
23.10. Diazotization; Reactions of Diazonium Ions
23.11. Synthesis of Amines
23.12. Use and Occurrence of Amines

Chapter 24. Chemistry of Naphthalene and the Aromatic Heterocycles

24.1. Chemistry of Naphthalene
24.2. Introduction to the Aromatic Heterocycles
24.3. Chemistry of Furan, Pyrrole, and Thiophene
24.4. Synthesis of Indoles
24.5. Chemistry of Pyridine and Quinoline
24.6. Occurrence of Heterocyclic Compounds

Chapter 25. Pericyclic Reactions

25.1. Molecular Orbitals of Conjugated pi-Electron Systems
25.2. Electrocyclic Reactions
25.3. Cycloaddition Reactions
25.4. Sigmatropic Reactions
25.5. Summary of the Pericyclic Selection Rules
25.6. Fluxional Molecules
25.7. Formation of Vitamin D

Chapter 26. The Chemistry of Amino Acids, Peptides, and Proteins

26.1. Nomenclature of Amino Acids and Peptides
26.2. Stereochemistry of the alpha-Amino Acids
26.3. Acid-Base Properties of Amino Acids and Peptides
26.4. Synthesis and Enantiomeric Resolution of alpha-Amino Acids
26.5. Acylation and Esterification Reactions of Amino Acids
26.6. Determination of Peptide Structure
26.7. Solid-Phase Peptide Synthesis
26.8. Combinatorial Chemistry
26.9. Structures of Peptides and Proteins
26.10. Enzymes: Biological Catalysts
26.11. Occurrence of Peptides and Proteins

Chapter 27. Carbohydrates and Nucleic Acids

27.1. Classification and Properties of Carbohydrates
27.2. Structures of the Monosaccharides
27.3. Mutarotation of Carbohydrates
27.4. Base-Catalyzed Isomerization of Aldoses and Ketoses
27.5. Glycosides
27.6. Ether and Ester Derivatives of Carbohydrates
27.7. Oxidation and Reduction Reactions of Carbohydrates
27.8. Kiliani-Fischer Synthesis
27.9. Proof of Glucose Stereochemistry
27.10. Disaccharides and Polysaccharides
27.11. Nucelosides, Nucleotides, and Nucleic Acids
27.12. DNA, RNA, and the Genetic Code

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Other Editions of Organic Chemistry / With CD-ROM

Organic Chemistry by Marc Loudon - ISBN 9780805366501