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Organic Chemistry

By William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

8th Edition © 2018
Discipline:Chemistry
Course:Organic Chemistry
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ORGANIC CHEMISTRY is a student-friendly, cutting edge introduction for chemistry, health, and the biological sciences majors. In the Eighth Edition, award-winning authors build on unified mechanistic themes, focused problem-solving, applied pharmaceutical problems and biological examples. Stepwise reaction mechanisms emphasize similarities among mechanisms using four traits: breaking a bond, making a new bond, adding a proton, and taking a proton away. Pull-out organic chemistry reaction roadmaps designed stepwise by chapter help students devise their own reaction pathways. Additional features designed to ensure student success include in-margin highlighted integral concepts, new end-of-chapter study guides, and worked examples. This edition also includes brand new author-created videos. Emphasizing “how-to” skills, this edition is packed with challenging synthesis problems, medicinal chemistry problems, and unique roadmap problems.

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AboutTable of contentsResourcesPricing & formatsRelated products

About this product

ORGANIC CHEMISTRY is a student-friendly, cutting edge introduction for chemistry, health, and the biological sciences majors. In the Eighth Edition, award-winning authors build on unified mechanistic themes, focused problem-solving, applied pharmaceutical problems and biological examples. Stepwise reaction mechanisms emphasize similarities among mechanisms using four traits: breaking a bond, making a new bond, adding a proton, and taking a proton away. Pull-out organic chemistry reaction roadmaps designed stepwise by chapter help students devise their own reaction pathways. Additional features designed to ensure student success include in-margin highlighted integral concepts, new end-of-chapter study guides, and worked examples. This edition also includes brand new author-created videos. Emphasizing “how-to” skills, this edition is packed with challenging synthesis problems, medicinal chemistry problems, and unique roadmap problems.

PRESENTATION OF MECHANISMS: Mechanisms are presented in a clear, stepwise fashion with written commentary accompanying each mechanistic step so verbal learners can learn alongside more visually oriented learners. Many mechanisms are broken into multiple steps to increase student understanding. In addition, the authors emphasize similarities between related mechanisms using just four different characteristics: breaking a bond, making a new bond, adding a proton, and taking a proton away. “Things You Should Know III, Reaction Mechanisms,” sets this explanation apart for easy reference.

ORGANIC CHEMISTRY REACTION ROADMAPS: Creating a cumulative, graphical representation of the different reactions students encounter in the context of important functional groups, organic chemistry roadmap inserts help students visualize how to interconvert different functional groups (which often require different reactions from different chapters) by simply identifying the most direct path on the roadmap. Unique end-of-chapter problems relate to the authors' organic chemistry roadmap.

IN-CHAPTER WORKED EXAMPLES: Featuring a pedagogy normally reserved for general chemistry texts, the book offers worked examples followed by corresponding problems without answers and a multitude of end-of-chapter problems, including challenging, research-based essay problems, multi-step synthesis problems, reactions in context problems, and roadmap problems.

"HOW-TO" BOXES: To facilitate student success in the course, insightful "How-To" boxes highlight the survival skills necessary to learn and master organic chemistry. Integrated throughout the text at key points, these essential skills include "How To: Draw Curved Arrows and Push Electrons," "How To: Draw Chiral Molecules," "How To: Solve NMR Spectral Problems," and many more.

Table of contents

Chapters

Cover Page
Title Page
Copyright Page
Dedication
About the Authors
Preface
Acknowledgements
Chapter 1. Covalent Bonding and Shapes of Molecules*Preview this chapter
I. Things You Should Know: General Conclusions from Quantum Mechanics
Chapter 2. Alkanes and Cycloalkanes
Chapter 3. Stereoisomerism and Chirality
Chapter 4. Acids and Bases
Chapter 5. Alkenes: Bonding, Nomenclature, and Properties
II. Things You Should Know: Nucleophiles and Electrophiles
III. Things You Should Know: Reaction Mechanisms
Chapter 6. Reactions of Alkenes
Chapter 7. Alkynes
Chapter 8. Haloalkanes, Halogenation, and Radical Reactions
IV. Things You Should Know: Common Mistakes in Arrow Pushing
Chapter 9. Nucleophilic Substitution and β-Elimination
Chapter 10. Alcohols
Chapter 11. Ethers, Epoxides, and Sulfides
Chapter 12. Infrared Spectroscopy
Chapter 13. Nuclear Magnetic Resonance Spectroscopy
Chapter 14. Mass Spectrometry
Chapter 15. An Introduction to Organometallic Compounds
Chapter 16. Aldehydes and Ketones
Chapter 17. Carboxylic Acids
V. Things You Should Know: Carboxylic Acid Derivative Reaction Mechanisms
Chapter 18. Functional Derivatives of Carboxylic Acids
Chapter 19. Enolate Anions and Enamines
Chapter 20. Dienes, Conjugated Systems, and Pericyclic Reactions
Chapter 21. Benzene and the Concept of Aromaticity
Chapter 22. Reactions of Benzene and Its Derivatives
Chapter 23. Amines
Chapter 24. Catalytic Carbon-Carbon Bond Formation
Chapter 25. Carbohydrates
Chapter 26. Lipids
Chapter 27. Amino Acids and Proteins
Chapter 28. Nucleic Acids
Chapter 29. Organic Polymer Chemistry
Media Index
Appendix 1. Thermodynamics and the Equilibrium Constant
Appendix 2. Major Classes of Organic Acids
Appendix 3. Bond Dissociation Enthalpies
Appendix 4. Characteristic H-NMR1 Chemical Shifts
Appendix 5. Characteristic C-NMR13 Chemical Shifts
Appendix 6. Characteristic Infrared Absorption Frequencies
Appendix 7. Electrostatic Potential Maps
Appendix 8. Summary of Stereochemical Terms
Appendix 9. Summary of the Rules of Nomenclature
Appendix 10. Organic Chemistry Road Maps
Appendix 11. Important Organic Functional Groups and Periodic Table of the Elements
Show more

Chapter 1. Covalent Bonding and Shapes of MoleculesPreview this chapter ↗

1.1
Electronic Structure of Atoms
Preview this section ↗
A. Electron Configuration of Atoms ↗
B. The Concept of Energy ↗
C. Lewis Dot Structures ↗
1.2
Lewis Model of Bonding
Preview this section ↗
A. Formation of Chemical Bonds ↗
B. Electronegativity and Chemical Bonds ↗
C. Lewis Structures for Molecules and Polyatomic Ions ↗
D. Formal Charge ↗
E. Exceptions to the Octet Rule ↗
F. Dative Bonds ↗
1.3
Functional Groups
Preview this section ↗
A. Alcohols ↗
B. Amines ↗
C. Aldehydes and Ketones ↗
D. Carboxylic Acids ↗
E. Carboxylic Esters ↗
F. Carboxylic Amides ↗
1.4
Bond Angles and Shapes of Molecules ↗
1.5
Polar and Nonpolar Molecules ↗
1.6
Quantum or Wave Mechanics
Preview this section ↗
A. Moving Particles Exhibit the Properties of a Wave ↗
B. Shapes of Atomic s and p Orbitals ↗
1.7
A Combined Valence Bond and Molecular Orbital Theory Approach to Covalent Bonding
Preview this section ↗
A. Molecular Orbital Theory; Formation of Molecular Orbitals ↗
B. Valence Bond Theory; Hybridization of Atomic Orbitals ↗
C. An Analysis of S and P ↗
D. Combining Valence Bond (VB) and Molecular Orbital (MO) Theories: The Creation of σ and π Bonding and Antibonding Orbitals ↗
1.8
Resonance
Preview this section ↗
A. Theory of Resonance ↗
B. Rules for Writing Acceptable Contributing Structures ↗
C. Estimating the Relative Importance of Contributing Structures ↗
1.9
Molecular Orbitals for Delocalized Systems
Preview this section ↗
A. Resonance Revisited ↗
B. A Greater Reliance on Molecular Orbital Theory ↗
C. Hybridization Considerations in Light of Resonance and MO Theory ↗
1.10
Bond Lengths and Bond Strengths in Alkanes, Alkenes, and Alkynes ↗
Study Guide ↗
Problems ↗
Electronic Structure of Atoms ↗
Lewis Structures and Formal Charge ↗
Polarity of Covalent Bonds ↗
Bond Angles and Shapes of Molecules ↗
Functional Groups ↗
Polar and Nonpolar Molecules ↗
Resonance and Contributing Structures ↗
Valence Bond Theory ↗
Combined MO/VB Theory ↗
Additional Problems ↗
Looking Ahead ↗
Molecular Orbitals ↗
Show more

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