Organic Chemistry
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Description
Contents
Reviews
Language
Unknown
ISBN
978-1-711471-85-3
Contents
Dedication and Preface
Chapter 1 Structure and Bonding
Why This Chapter?
1.1 Atomic Structure: The Nucleus
1.2 Atomic Structure: Orbitals
1.3 Atomic Structure: Electron Configurations
1.4 Development of Chemical Bonding Theory
1.5 Describing Chemical Bonds: Valence Bond Theory
1.6 sp3 Hybrid Orbitals and the Structure of Methane
1.7 sp3 Hybrid Orbitals and the Structure of Ethane
1.8 sp2 Hybrid Orbitals and the Structure of Ethylene
1.9 sp Hybrid Orbitals and the Structure of Acetylene
1.10 Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
1.11 Describing Chemical Bonds: Molecular Orbital Theory
1.12 Drawing Chemical Structures
Chemistry Matters — Organic Foods: Risk versus Benefit
Key Terms
Summary
Additional Problems
Chapter 2 Polar Covalent Bonds; Acids and Bases
Why This Chapter?
2.1 Polar Covalent Bonds and Electronegativity
2.2 Polar Covalent Bonds and Dipole Moments
2.3 Formal Charges
2.4 Resonance
2.5 Rules for Resonance Forms
2.6 Drawing Resonance Forms
2.7 Acids and Bases: The Brønsted–Lowry Definition
2.8 Acid and Base Strength
2.9 Predicting Acid–Base Reactions from pKa Values
2.10 Organic Acids and Organic Bases
2.11 Acids and Bases: The Lewis Definition
2.12 Noncovalent Interactions between Molecules
Chemistry Matters — Alkaloids: From Cocaine to Dental Anesthetics
Key Terms
Summary
Additional Problems
Chapter 3 Organic Compounds: Alkanes and Their Stereochemistry
Why This Chapter?
3.1 Functional Groups
3.2 Alkanes and Alkane Isomers
3.3 Alkyl Groups
3.4 Naming Alkanes
3.5 Properties of Alkanes
3.6 Conformations of Ethane
3.7 Conformations of Other Alkanes
Chemistry Matters — Gasoline
Key Terms
Summary
Additional Problems
Chapter 4 Organic Compounds: Cycloalkanes and Their Stereochemistry
Why This Chapter?
4.1 Naming Cycloalkanes
4.2 Cis–Trans Isomerism in Cycloalkanes
4.3 Stability of Cycloalkanes: Ring Strain
4.4 Conformations of Cycloalkanes
4.5 Conformations of Cyclohexane
4.6 Axial and Equatorial Bonds in Cyclohexane
4.7 Conformations of Monosubstituted Cyclohexanes
4.8 Conformations of Disubstituted Cyclohexanes
4.9 Conformations of Polycyclic Molecules
Chemistry Matters — Molecular Mechanics
Key Terms
Summary
Additional Problems
Chapter 5 Stereochemistry at Tetrahedral Centers
Why This Chapter?
5.1 Enantiomers and the Tetrahedral Carbon
5.2 The Reason for Handedness in Molecules: Chirality
5.3 Optical Activity
5.4 Pasteur’s Discovery of Enantiomers
5.5 Sequence Rules for Specifying Configuration
5.6 Diastereomers
5.7 Meso Compounds
5.8 Racemic Mixtures and the Resolution of Enantiomers
5.9 A Review of Isomerism
5.10 Chirality at Nitrogen, Phosphorus, and Sulfur
5.11 Prochirality
5.12 Chirality in Nature and Chiral Environments
Chemistry Matters — Chiral Drugs
Key Terms
Summary
Additional Problems
Chapter 6 An Overview of Organic Reactions
Why This Chapter?
6.1 Kinds of Organic Reactions
6.2 How Organic Reactions Occur: Mechanisms
6.3 Polar Reactions
6.4 An Example of a Polar Reaction: Addition of HBr to Ethylene
6.5 Using Curved Arrows in Polar Reaction Mechanisms
6.6 Radical Reactions
6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes
6.8 Describing a Reaction: Bond Dissociation Energies
6.9 Describing a Reaction: Energy Diagrams and Transition States
6.10 Describing a Reaction: Intermediates
6.11 A Comparison Between Biological Reactions and Laboratory Reactions
Chemistry Matters — Where Do Drugs Come From?
Key Terms
Summary
Additional Problems
Chapter 7 Alkenes: Structure and Reactivity
Why This Chapter?
7.1 Industrial Preparation and Use of Alkenes
7.2 Calculating the Degree of Unsaturation
7.3 Naming Alkenes
7.4 Cis–Trans Isomerism in Alkenes
7.5 Alkene Stereochemistry and the E,Z Designation
7.6 Stability of Alkenes
7.7 Electrophilic Addition Reactions of Alkenes
7.8 Orientation of Electrophilic Additions: Markovnikov’s Rule
7.9 Carbocation Structure and Stability
7.10 The Hammond Postulate
7.11 Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements
Chemistry Matters — Bioprospecting: Hunting for Natural Products
Key Terms
Summary
Additional Problems
Chapter 8 Alkenes: Reactions and Synthesis
Why This Chapter?
8.1 Preparing Alkenes: A Preview of Elimination Reactions
8.2 Halogenation of Alkenes: Addition of X2
8.3 Halohydrins from Alkenes: Addition of HO-X
8.4 Hydration of Alkenes: Addition of H2O by Oxymercuration
8.5 Hydration of Alkenes: Addition of H2O by Hydroboration
8.6 Reduction of Alkenes: Hydrogenation
8.7 Oxidation of Alkenes: Epoxidation and Hydroxylation
8.8 Oxidation of Alkenes: Cleavage to Carbonyl Compounds
8.9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis
8.10 Radical Additions to Alkenes: Chain-Growth Polymers
8.11 Biological Additions of Radicals to Alkenes
8.12 Reaction Stereochemistry: Addition of H2O to an Achiral Alkene
8.13 Reaction Stereochemistry: Addition of H2O to a Chiral Alkene
Chemistry Matters — Terpenes: Naturally Occurring Alkenes
Key Terms
Summary
Summary of Reactions
Additional Problems
Chapter 9 Alkynes: An Introduction to Organic Synthesis
Why This Chapter?
9.1 Naming Alkynes
9.2 Preparation of Alkynes: Elimination Reactions of Dihalides
9.3 Reactions of Alkynes: Addition of HX and X2
9.4 Hydration of Alkynes
9.5 Reduction of Alkynes
9.6 Oxidative Cleavage of Alkynes
9.7 Alkyne Acidity: Formation of Acetylide Anions
9.8 Alkylation of Acetylide Anions
9.9 An Introduction to Organic Synthesis
Chemistry Matters — The Art of Organic Synthesis
Key Terms
Summary
Summary of Reactions
Additional Problems
Chapter 10 Organohalides
Why This Chapter?
10.1 Names and Structures of Alkyl Halides
10.2 Preparing Alkyl Halides from Alkanes: Radical Halogenation
10.3 Preparing Alkyl Halides from Alkenes: Allylic Bromination
10.4 Stability of the Allyl Radical: Resonance Revisited
10.5 Preparing Alkyl Halides from Alcohols
10.6 Reactions of Alkyl Halides: Grignard Reagents
10.7 Organometallic Coupling Reactions
10.8 Oxidation and Reduction in Organic Chemistry
Chemistry Matters — Naturally Occurring Organohalides
Key Terms
Summary
Summary of Reactions
Additional Problems
Chapter 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
Why This Chapter?
11.1 The Discovery of Nucleophilic Substitution Reactions
11.2 The SN2 Reaction
11.3 Characteristics of the SN2 Reaction
11.4 The SN1 Reaction
11.5 Characteristics of the SN1 Reaction
11.6 Biological Substitution Reactions
11.7 Elimination Reactions: Zaitsev’s Rule
11.8 The E2 Reaction and the Deuterium Isotope Effect
11.9 The E2 Reaction and Cyclohexane Conformation
11.10 The E1 and E1cB Reactions
11.11 Biological Elimination Reactions
11.12 A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2
Chemistry Matters — Green Chemistry
Key Terms
Summary
Summary of Reactions
Additional Problems
Chapter 12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy
Why This Chapter?
12.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
12.2 Interpreting Mass Spectra
12.3 Mass Spectrometry of Some Common Functional Groups
12.4 Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments
12.5 Spectroscopy and the Electromagnetic Spectrum
12.6 Infrared Spectroscopy
12.7 Interpreting Infrared Spectra
12.8 Infrared Spectra of Some Common Functional Groups
Chemistry Matters — X-Ray Crystallography
Key Terms
Summary
Additional Problems
Appendix A Nomenclature of Polyfunctional Organic Compounds
Name Part 1. The Suffix: Functional-Group Precedence
Name Part 2. The Parent: Selecting the Main Chain or Ring
Name Parts 3 and 4. The Prefixes and Locants
Writing the Name
Additional Reading
Appendix B Acidity Constants for Some Organic Compounds
Appendix C Periodic Table
Answer Key
Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 9
Chapter 10
Chapter 11
Chapter 12
Index
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