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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
Chapter 1 Test Chapter
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1 Test Chapter
Organic
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Chemistry
1 Test Organic
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Principles
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Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
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Principles and
Comprehensive
Study
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Guide With
Comprehensive
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Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
,Chapter 1 Test Chapter
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1 Test Chapter
Organic
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Chemistry
1 Test Organic
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Principles
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Chemistry
and
Organic
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Principles
Chemistry
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Comprehensive
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Guide With Solution.pdf
W. W. Norton & Company has been independent since its founding in 1923, when William Warder Norton and Mary D. Herter Norton
first published lectures delivered at the People’s Institute, the adult education division of New York City’s Cooper Union. The firm soon
expanded its program beyond the Institute, publishing books by celebrated academics from America and abroad. By midcentury, the two
major pillars of Norton’s publishing program—trade books and college texts—were firmly established. In the 1950s, the Norton family
transferred control of the company to its employees, and today—with a staff of four hundred and a comparable number of trade, college,
and professional titles published each year—W. W. Norton & Company stands as the largest and oldest publishing house owned wholly by
its employees.
Copyright © 2018, 2014 by W. W. Norton & Company, Inc.
All rights reserved.
Associate Media Editor: Arielle Holstein
Associate Managing Editor, College: Carla L. Talmadge
Production Manager: Eric Pier-Hocking
Assistant Media Editor: Doris Chiu
Composition by Westchester Publishing Services
W. W. Norton & Company, Inc., 500 Fifth Avenue, New York, NY 10110
wwnorton.com
W. W. Norton & Company Ltd., 15 Carlisle Street, London W1D 3BS
1234567890
Chapter 1 Test Chapter
Bank Answers
1 Test Chapter
Organic
Bank Answers
Chemistry
1 Test Organic
Bank
Principles
Answers
Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
,Chapter 1 Test Chapter
Bank Answers
1 Test Chapter
Organic
Bank Answers
Chemistry
1 Test Organic
Bank
Principles
Answers
Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
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
Chapter 1 Test Chapter
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1 Test Chapter
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Chemistry
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Organic
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Chemistry
and
Comprehensive
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Principles and
Comprehensive
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Guide With
Comprehensive
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Solution.pdf
Guide WithStudy
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Guide With Solution.pdf
, Chapter 1 Test Chapter
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1 Test Chapter
Organic
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Chemistry
1 Test Organic
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Principles
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Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
Chapter 12 | Electrophilic Addition to Nonpolar Bonds 2: Reactions Involving Cyclic Transi-
tion States 298
Chapter 13 | Organic Synthesis 1: Beginning Concepts in Designing Multistep Synthesis 319
Chapter 14 | Orbital Interactions 2: Extended Systems, Conjugation, and Aromaticity 341
Chapter 15 | Structure Determination 1: Ultraviolet–Visible and Infrared Spectroscopies 359
Chapter 16 | Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass
Spectrometry 380
Chapter 17 | Nucleophilic Addition to Polar Bonds 1: Addition of Strong Nucleophiles 404
Chapter 18 | Nucleophilic Addition to Polar Bonds 2: Weak Nucleophiles and Acid and Base
Catalysis 429
Chapter 19 | Organic Synthesis 2: Intermediate Topics in Synthesis Design, and Useful Redox
and Carbon–Carbon Bond-Forming Reactions 457
Chapter 20 | Nucleophilic Addition–Elimination Reactions 1: The General Mechanism Involv-
ing Strong Nucleophiles 485
Chapter 21 | Nucleophilic Addition–Elimination Reactions 2: Weak Nucleophiles 511
Chapter 22 | Aromatic Substitution 1: Electrophilic Aromatic Substitution on Benzene; Useful
Accompanying Reactions 541
Chapter 23 | Aromatic Substitution 2: Reactions of Substituted Benzenes and Other Rings 564
Chapter 24 | The Diels–Alder Reaction and Other Pericyclic Reactions 590
Chapter 25 | Reactions Involving Free Radicals 616
Interchapter G | Fragmentation Pathways in Mass Spectrometry 639
Chapter 26 | Polymers 653
Credits 672
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1 Test Chapter
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Chemistry
1 Test Organic
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Chemistry
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Organic
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Principles
Chemistry
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Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
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Solution.pdf
Guide WithStudy
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Guide With Solution.pdf
Bank Answers
1 Test Chapter
Organic
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Chemistry
1 Test Organic
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Principles
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Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
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
Chapter 1 Test Chapter
Bank Answers
1 Test Chapter
Organic
Bank Answers
Chemistry
1 Test Organic
Bank
Principles
Answers
Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
,Chapter 1 Test Chapter
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1 Test Chapter
Organic
Bank Answers
Chemistry
1 Test Organic
Bank
Principles
Answers
Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
W. W. Norton & Company has been independent since its founding in 1923, when William Warder Norton and Mary D. Herter Norton
first published lectures delivered at the People’s Institute, the adult education division of New York City’s Cooper Union. The firm soon
expanded its program beyond the Institute, publishing books by celebrated academics from America and abroad. By midcentury, the two
major pillars of Norton’s publishing program—trade books and college texts—were firmly established. In the 1950s, the Norton family
transferred control of the company to its employees, and today—with a staff of four hundred and a comparable number of trade, college,
and professional titles published each year—W. W. Norton & Company stands as the largest and oldest publishing house owned wholly by
its employees.
Copyright © 2018, 2014 by W. W. Norton & Company, Inc.
All rights reserved.
Associate Media Editor: Arielle Holstein
Associate Managing Editor, College: Carla L. Talmadge
Production Manager: Eric Pier-Hocking
Assistant Media Editor: Doris Chiu
Composition by Westchester Publishing Services
W. W. Norton & Company, Inc., 500 Fifth Avenue, New York, NY 10110
wwnorton.com
W. W. Norton & Company Ltd., 15 Carlisle Street, London W1D 3BS
1234567890
Chapter 1 Test Chapter
Bank Answers
1 Test Chapter
Organic
Bank Answers
Chemistry
1 Test Organic
Bank
Principles
Answers
Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
,Chapter 1 Test Chapter
Bank Answers
1 Test Chapter
Organic
Bank Answers
Chemistry
1 Test Organic
Bank
Principles
Answers
Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
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
Chapter 1 Test Chapter
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1 Test Chapter
Organic
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Chemistry
1 Test Organic
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Principles
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Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
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Guide With
Comprehensive
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Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
, Chapter 1 Test Chapter
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1 Test Chapter
Organic
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Chemistry
1 Test Organic
Bank
Principles
Answers
Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
Mechanisms
Guide With
Comprehensive
Study
Solution.pdf
Guide WithStudy
Solution.pdf
Guide With Solution.pdf
Chapter 12 | Electrophilic Addition to Nonpolar Bonds 2: Reactions Involving Cyclic Transi-
tion States 298
Chapter 13 | Organic Synthesis 1: Beginning Concepts in Designing Multistep Synthesis 319
Chapter 14 | Orbital Interactions 2: Extended Systems, Conjugation, and Aromaticity 341
Chapter 15 | Structure Determination 1: Ultraviolet–Visible and Infrared Spectroscopies 359
Chapter 16 | Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass
Spectrometry 380
Chapter 17 | Nucleophilic Addition to Polar Bonds 1: Addition of Strong Nucleophiles 404
Chapter 18 | Nucleophilic Addition to Polar Bonds 2: Weak Nucleophiles and Acid and Base
Catalysis 429
Chapter 19 | Organic Synthesis 2: Intermediate Topics in Synthesis Design, and Useful Redox
and Carbon–Carbon Bond-Forming Reactions 457
Chapter 20 | Nucleophilic Addition–Elimination Reactions 1: The General Mechanism Involv-
ing Strong Nucleophiles 485
Chapter 21 | Nucleophilic Addition–Elimination Reactions 2: Weak Nucleophiles 511
Chapter 22 | Aromatic Substitution 1: Electrophilic Aromatic Substitution on Benzene; Useful
Accompanying Reactions 541
Chapter 23 | Aromatic Substitution 2: Reactions of Substituted Benzenes and Other Rings 564
Chapter 24 | The Diels–Alder Reaction and Other Pericyclic Reactions 590
Chapter 25 | Reactions Involving Free Radicals 616
Interchapter G | Fragmentation Pathways in Mass Spectrometry 639
Chapter 26 | Polymers 653
Credits 672
Chapter 1 Test Chapter
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1 Test Chapter
Organic
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Chemistry
1 Test Organic
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Principles
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Chemistry
and
Organic
Mechanisms
Principles
Chemistry
and
Comprehensive
Mechanisms
Principles and
Comprehensive
Study
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Guide With
Comprehensive
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Guide With Solution.pdf
