TEST BANK
All Chapters Included
,Organic Chemistry:
Princi ples and
Mechanisms
Second Edition
Joel M. Karty
James Wollack
ST. CATHERINE UNIVERSITY
Christopher Markworth
WESTERN WASHINGTON UNIVERSITY
Jennifer Griffith
WESTERN WASHINGTON UNIVERSITY
n W • W • NORTON & COM PANY • NEW YORK • LONDON
, CONTENTS Preface v
Chapter 1 | Atomic and Molecular Structure 1
Interchapter A | Nomenclature: The Basic System for Naming S imple Organic
Compounds— Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes,
and Ethers 35
Chapter 2 | Three- Dimensional Geometry, Intermolecular Interactions, and
Physical Properties 47
Chapter 3 | Orbital Interactions 1: Hybridization and Two- Center Molecular Orbitals 75
Interchapter B | Naming Alkenes, Alkynes, and Benzene Derivatives 103
Chapter 4 | Isomerism 1: Conformers and Constitutional Isomers 114
Chapter 5 | Isomerism 2: Chirality, Enantiomers, and Diastereomers 143
Interchapter C | Stereochemistry in Nomenclature: R and S Configurations about
Asymmetric Carbons and Z and E Configurations about Double Bonds 172
Chapter 6 | The Proton Transfer Reaction: An Introduction to Mechanisms,
Thermodynamics, and Charge Stability 184
Chapter 7 | An Overview of the Most Common Elementary Steps 211
Interchapter D | Molecular Orbital Theory, Hyperconjugation, and Chemical Reactions 243
Interchapter E | Naming Compounds with a Functional Group That Calls for a
Suffix 1: Alcohols, Amines, Ketones, and Aldehydes 254
Chapter 8 | An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and
Their Comparisons to SN2 and E2 Reactions 265
Chapter 9 | Nucleophilic Substitution and Elimination Reactions 1: Competition
among SN2, SN1, E2, and E1 Reactions 292
Interchapter F | Naming Compounds with a Functional Group That Calls for a
Suffix 2: Carboxylic Acids and Their Derivatives 320
Chapter 10 | Nucleophilic Substitution and Elimination Reactions 2: Reactions
That Are Useful for Synthesis 331
Chapter 11 | Electrophilic Addition to Nonpolar π Bonds 1: Addition of a Brønsted
Acid 361
Chapter 12 | Electrophilic Addition to Nonpolar π Bonds 2: Reactions Involving
Cyclic Transition States 388
, Chapter 13 | Organic Synthesis 1: Beginning Concepts in Designing Multistep Synthesis 415
Chapter 14 | Orbital Interactions 2: Extended π Systems, Conjugation, and Aromaticity 445
Chapter 15 | Structure Determination 1: Ultraviolet– Vis i ble and Infrared Spectroscopies 469
Chapter 16 | Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy
and Mass Spectrometry 500
Chapter 17 | Nucleophilic Addition to Polar π Bonds 1: Addition of Strong Nucleophiles 533
Chapter 18 | Nucleophilic Addition to Polar π Bonds 2: Weak Nucleophiles and Acid
and Base Catalysis 567
Chapter 19 | Organic Synthesis 2: Intermediate Topics in Synthesis Design, and
Useful Redox and Carbon– Carbon Bond- Forming Reactions 606
Chapter 20 | Nucleophilic Addition– Elimination Reactions 1: The General
Mechanism Involving Strong Nucleophiles 645
Chapter 21 | Nucleophilic Addition– Elimination Reactions 2: Weak Nucleophiles 681
Chapter 22 | Aromatic Substitution 1: Electrophilic Aromatic Substitution on
Benzene; Useful Accompanying Reactions 723
Chapter 23 | Aromatic Substitution 2: Reactions of Substituted Benzenes and Other Rings 752
Chapter 24 | The Diels– Alder Reaction and Other Pericyclic Reactions 790
Chapter 25 | Reactions Involving Free Radicals 826
Interchapter G | Fragmentation Pathways in Mass Spectrometry 856
Chapter 26 | Polymers 876
Credits 902
Chapter 1: atomic and Molecular Structure
All Chapters Included
,Organic Chemistry:
Princi ples and
Mechanisms
Second Edition
Joel M. Karty
James Wollack
ST. CATHERINE UNIVERSITY
Christopher Markworth
WESTERN WASHINGTON UNIVERSITY
Jennifer Griffith
WESTERN WASHINGTON UNIVERSITY
n W • W • NORTON & COM PANY • NEW YORK • LONDON
, CONTENTS Preface v
Chapter 1 | Atomic and Molecular Structure 1
Interchapter A | Nomenclature: The Basic System for Naming S imple Organic
Compounds— Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes,
and Ethers 35
Chapter 2 | Three- Dimensional Geometry, Intermolecular Interactions, and
Physical Properties 47
Chapter 3 | Orbital Interactions 1: Hybridization and Two- Center Molecular Orbitals 75
Interchapter B | Naming Alkenes, Alkynes, and Benzene Derivatives 103
Chapter 4 | Isomerism 1: Conformers and Constitutional Isomers 114
Chapter 5 | Isomerism 2: Chirality, Enantiomers, and Diastereomers 143
Interchapter C | Stereochemistry in Nomenclature: R and S Configurations about
Asymmetric Carbons and Z and E Configurations about Double Bonds 172
Chapter 6 | The Proton Transfer Reaction: An Introduction to Mechanisms,
Thermodynamics, and Charge Stability 184
Chapter 7 | An Overview of the Most Common Elementary Steps 211
Interchapter D | Molecular Orbital Theory, Hyperconjugation, and Chemical Reactions 243
Interchapter E | Naming Compounds with a Functional Group That Calls for a
Suffix 1: Alcohols, Amines, Ketones, and Aldehydes 254
Chapter 8 | An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and
Their Comparisons to SN2 and E2 Reactions 265
Chapter 9 | Nucleophilic Substitution and Elimination Reactions 1: Competition
among SN2, SN1, E2, and E1 Reactions 292
Interchapter F | Naming Compounds with a Functional Group That Calls for a
Suffix 2: Carboxylic Acids and Their Derivatives 320
Chapter 10 | Nucleophilic Substitution and Elimination Reactions 2: Reactions
That Are Useful for Synthesis 331
Chapter 11 | Electrophilic Addition to Nonpolar π Bonds 1: Addition of a Brønsted
Acid 361
Chapter 12 | Electrophilic Addition to Nonpolar π Bonds 2: Reactions Involving
Cyclic Transition States 388
, Chapter 13 | Organic Synthesis 1: Beginning Concepts in Designing Multistep Synthesis 415
Chapter 14 | Orbital Interactions 2: Extended π Systems, Conjugation, and Aromaticity 445
Chapter 15 | Structure Determination 1: Ultraviolet– Vis i ble and Infrared Spectroscopies 469
Chapter 16 | Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy
and Mass Spectrometry 500
Chapter 17 | Nucleophilic Addition to Polar π Bonds 1: Addition of Strong Nucleophiles 533
Chapter 18 | Nucleophilic Addition to Polar π Bonds 2: Weak Nucleophiles and Acid
and Base Catalysis 567
Chapter 19 | Organic Synthesis 2: Intermediate Topics in Synthesis Design, and
Useful Redox and Carbon– Carbon Bond- Forming Reactions 606
Chapter 20 | Nucleophilic Addition– Elimination Reactions 1: The General
Mechanism Involving Strong Nucleophiles 645
Chapter 21 | Nucleophilic Addition– Elimination Reactions 2: Weak Nucleophiles 681
Chapter 22 | Aromatic Substitution 1: Electrophilic Aromatic Substitution on
Benzene; Useful Accompanying Reactions 723
Chapter 23 | Aromatic Substitution 2: Reactions of Substituted Benzenes and Other Rings 752
Chapter 24 | The Diels– Alder Reaction and Other Pericyclic Reactions 790
Chapter 25 | Reactions Involving Free Radicals 826
Interchapter G | Fragmentation Pathways in Mass Spectrometry 856
Chapter 26 | Polymers 876
Credits 902
Chapter 1: atomic and Molecular Structure
