TEST BANK
Organic Chemistry: Prin-
ciples and Mechanisms
Second Edition
Joel M. Karty
James Wollack
ST. CATHERINE UNIVERSITY
Christopher Markworth
WESTERN WASHINGTON UNIVERSITY
Jennifer Griffith
WESTERN WASHINGTON UNIVERSITY
W • W • NORTON & COMPANY • NEW YORK • LONDON
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CONTENTS
Preface 5
Chapter 1 | Atomic and Molecular Structure 40
Interchapter A | Nomenclature: The Basic System for Naming Simple Organic Compounds—
Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes, and Ethers 31
Chapter 2 | Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties
40
Chapter 3 | Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals 60
Interchapter B | Naming Alkenes, Alkynes, and Benzene Derivatives 81
Chapter 4 | Isomerism 1: Conformers and Constitutional Isomers 90
Chapter 5 | Isomerism 2: Chirality, Enantiomers, and Diastereomers 112
Interchapter C | Stereochemistry in Nomenclature: R and S Configurations about Asymmetric
Carbons and Z and E Configurations about Double Bonds 134
Chapter 6 | The Proton Transfer Reaction: An Introduction to Mechanisms, Thermodynamics,
and Charge Stability 144
Chapter 7 | An Overview of the Most Common Elementary Steps 164
Interchapter D | Molecular Orbital Theory, Hyperconjugation, and Chemical Reactions 187
Interchapter E | Naming Compounds with a Functional Group That Calls for a Suffix 1: Alco-
hols, Amines, Ketones, and Aldehydes 196
Chapter 8 | An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and Their Compar-
isons to SN2 and E2 Reactions 205
Chapter 9 | Nucleophilic Substitution and Elimination Reactions 1: Competition among S N2,
SN1, E2, and E1 Reactions 227
Interchapter F | Naming Compounds with a Functional Group That Calls for a Suffix 2: Carbox-
ylic Acids and Their Derivatives 247
Chapter 10 | Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful
for Synthesis 256
Chapter 11 | Electrophilic Addition to Nonpolar Bonds 1: Addition of a Brønsted Acid
278
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