, 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 172
Bonds 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 243
Reactions Interchapter E | Naming Compounds with a Functional Group That Calls
for a 254
Suffix 1: Alcohols, Amines, Ketones, and Aldehydes
Chapter 8 | An Introduction to Multistep Mechanisms: SN1 and E1 265
Reactions and Their Comparisons to SN2 and E2 Reactions
Chapter 9 | Nucleophilic Substitution and Elimination Reactions 1: 292
Competition among SN2, SN1, E2, and E1 Reactions
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 469
Spectroscopies 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 533
Nucleophiles
Chapter 18 | Nucleophilic Addition to Polar π Bonds 2: Weak Nucleophiles and 567
Acid and Base Catalysis
Chapter 19 | Organic Synthesis 2: Intermediate Topics in Synthesis Design, 606
and Useful Redox and Carbon– Carbon Bond- Forming Reactions
Chapter 20 | Nucleophilic Addition– Elimination Reactions 1: The General
Mechanism Involving Strong Nucleophiles 645
Chapter 21 | Nucleophilic Addition– Elimination Reactions 2: Weak 681
Nucleophiles 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
LearNING OBJeCtIVeS
Determine the number of valence and/or core electrons for an atom or
ion. Interpret the electron configuration and formal charge for an atom
or ion. Identify forces that are involved in chemical bonding.
Analyze an energy versus internuclear distance diagram to understand the properties of a chemical
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 172
Bonds 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 243
Reactions Interchapter E | Naming Compounds with a Functional Group That Calls
for a 254
Suffix 1: Alcohols, Amines, Ketones, and Aldehydes
Chapter 8 | An Introduction to Multistep Mechanisms: SN1 and E1 265
Reactions and Their Comparisons to SN2 and E2 Reactions
Chapter 9 | Nucleophilic Substitution and Elimination Reactions 1: 292
Competition among SN2, SN1, E2, and E1 Reactions
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 469
Spectroscopies 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 533
Nucleophiles
Chapter 18 | Nucleophilic Addition to Polar π Bonds 2: Weak Nucleophiles and 567
Acid and Base Catalysis
Chapter 19 | Organic Synthesis 2: Intermediate Topics in Synthesis Design, 606
and Useful Redox and Carbon– Carbon Bond- Forming Reactions
Chapter 20 | Nucleophilic Addition– Elimination Reactions 1: The General
Mechanism Involving Strong Nucleophiles 645
Chapter 21 | Nucleophilic Addition– Elimination Reactions 2: Weak 681
Nucleophiles 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
LearNING OBJeCtIVeS
Determine the number of valence and/or core electrons for an atom or
ion. Interpret the electron configuration and formal charge for an atom
or ion. Identify forces that are involved in chemical bonding.
Analyze an energy versus internuclear distance diagram to understand the properties of a chemical
