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Organic Chemistry
Principles and Mechanisms
Joel M. Karty
Elon University
b
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To Pnut, Fafa, and Jakers
About the Author
JOEL KARTY earned his B.S. in chemistry at the University of Puget Sound and his
Ph.D. at Stanford University. He joined the faculty of Elon University in 2001, where
he currently holds the rank of associate professor. He teaches primarily the organic
chemistry sequence and also teaches general chemistry. In the summer, Joel teaches at
the Summer Medical and Dental Education Program through the Duke University
medical center. His research interests include investigating the roles of resonance and
inductive effects in fundamental chemical systems and studying the mechanism of
pattern formation in Liesegang reactions. He has written a very successful student
supplement, Get Ready for Organic Chemistry, Second Edition (formerly called The
Nuts and Bolts of Organic Chemistry).
Brief Contents
1 Atomic and Molecular Structure 1 11 Electrophilic Addition to Nonpolar ě Bonds 1:
Addition of a Brønsted Acid 570
Nomenclature 1 Introduction: The Basic
System for Naming Simple Organic Compounds: 12 Electrophilic Addition to Nonpolar ě Bonds 2:
Alkanes, Cycloalkanes, Haloalkanes, Nitroalkanes, Reactions Involving Cyclic Transition States 610
and Ethers 54
13 Organic Synthesis 1: Beginning Concepts 645
2 Three-Dimensional Geometry, Intermolecular
14 Orbital Interactions 2: Extended ě Systems,
Interactions, and Physical Properties 76
Conjugation, and Aromaticity 676
3 Orbital Interactions 1: Hybridization and
15 Structure Determination 1: Ultraviolet-Visible
Two-Center Molecular Orbitals 128
and Infrared Spectroscopies 715
Nomenclature 2 Naming Alkenes, Alkynes, and
16 Structure Determination 2: Nuclear
Benzene Derivatives 163
Magnetic Resonance Spectroscopy and Mass
4 Isomerism 1: Conformational and Constitutional Spectrometry 757
Isomers 176
17 Nucleophilic Addition to Polar ě Bonds 1:
5 Isomerism 2: Chirality, Enantiomers, and Addition of Strong Nucleophiles 815
Diastereomers 224
18 Nucleophilic Addition to Polar ě Bonds 2:
Nomenclature 3 Considerations of Addition of Weak Nucleophiles and Acid and Base
Stereochemistry: R and S Configurations Catalysis 861
about Tetrahedral Stereocenters and Z and E
19 Organic Synthesis 2: Intermediate Topics
Configurations about Double Bonds 276
of Synthesis Design, and Useful Reduction and
6 The Proton Transfer Reaction: An Introduction Oxidation Reactions 919
to Mechanisms, Thermodynamics, and Charge
20 Nucleophilic Addition–Elimination Reactions 1:
Stability 295
The General Mechanism Involving Strong
7 An Overview of the Most Common Elementary Nucleophiles 962
Steps 351
21 Nucleophilic Addition–Elimination Reactions 2:
Interchapter 1 Molecular Orbital Theory and Weak Nucleophiles 1006
Chemical Reactions 388
22 Electrophilic Aromatic Substitution 1:
Nomenclature 4 Naming Compounds with Substitution on Benzene; Useful Accompanying
Common Functional Groups: Alcohols, Amines, Reactions 1065
Ketones, Aldehydes, Carboxylic Acids, Acid Halides,
23 Electrophilic Aromatic Substitution 2:
Acid Anhydrides, Nitriles, and Esters 398
Substitution Involving Mono- and Disubstituted
8 An Introduction to Multistep Mechanisms: SN1 Benzene and Other Aromatic Rings 1104
and E1 Reactions 420
24 The Diels–Alder Reaction and Other Pericyclic
9 Nucleophilic Substitution and Elimination Reactions 1154
Reactions 1: Competition among SN2, SN1, E2, and
25 Reactions Involving Free Radicals 1199
E1 Reactions 466
Interchapter 2 Fragmentation Pathways in
10 Nucleophilic Substitution and Elimination
Mass Spectrometry 1245
Reactions 2: Reactions That Are Useful for
Synthesis 524 26 Polymers 1255
ix
Contents
List of Interest Boxes xxvii
List of Mechanisms xxix
Preface xxxiii
1 Atomic and Molecular Structure 1
1.1 What Is Organic Chemistry? 2

1.2 Why Carbon? 3
1.3 Atomic Structure and Ground State Electron Configurations 4
1.4 The Covalent Bond: Bond Energy and Bond Length 8
1.5 Lewis Dot Structures and the Octet Rule 12
1.6 Strategies for Success: Drawing Lewis Dot Structures Quickly 15
1.7 Electronegativity, Polar Covalent Bonds, and Bond Dipoles 16
1.8 Ionic Bonds 18
1.9 Assigning Electrons to Atoms in Molecules:
Formal Charge and Oxidation State 20
1.10 Resonance Theory 22
1.11 Strategies for Success: Drawing All Resonance Structures 26
1.12 Shorthand Notations 32
1.13 An Overview of Organic Compounds: Functional Groups 35
1.14 Wrapping Up and Looking Ahead 39
The Organic Chemistry of Biomolecules
1.15 An Introduction to Proteins, Carbohydrates, and Nucleic Acids:
Fundamental Building Blocks and Functional Groups 39
Chapter Summary and Key Terms 47

Problems 47
Nomenclature
1 Introduction: The Basic System for

Naming Simple Organic Compounds
Alkanes, Cycloalkanes, Haloalkanes, Nitroalkanes,
and Ethers 54
N1.1 The Need for Systematic Nomenclature: An Introduction to the IUPAC

System 54
N1.2 Alkanes and Cycloalkanes: Roots, Prefixes, Isomers, and Number
Locators 56
N1.3 Trivial Names and Common Alkyl Substituents 68
N1.4 Substituents Other Than Alkyl Groups: Naming Haloalkanes,
Nitroalkanes, and Ethers 71
xi
2 Three-Dimensional Geometry,
Intermolecular Interactions, and
Physical Properties 76
2.1 Valence Shell Electron Pair Repulsion (VSEPR) Theory:
Three-Dimensional Geometry 77
2.2 Dash–Wedge Notation 81
2.3 Strategies for Success: The Molecular Modeling Kit 83
2.4 Net Molecular Dipoles and Dipole Moments 84
2.5 Physical Properties, Functional Groups, and Intermolecular
Interactions 87
2.6 Melting Points, Boiling Points, and Intermolecular Interactions 89
2.7 Solubility 98
2.8 Strategies for Success: Ranking Boiling Points and Solubilities of
Structurally Similar Compounds 103
2.9 Protic and Aprotic Solvents 106
2.10 Soaps and Detergents 109
2.12 An Introduction to Lipids 114

Problems 121
3 Orbital Interactions 1
Hybridization and Two-Center Molecular Orbitals 128
3.1 Atomic Orbitals and the Wave Nature of Electrons 129

3.2 Interaction between Orbitals: Constructive and Destructive
Interference 132
3.3 An Introduction to Molecular Orbital Theory and σ Bonds:
An Example with H2 134
3.4 Hybridized Atomic Orbitals 137
3.5 Valence Bond Theory and Other Orbitals of σ Symmetry: An Example
with Ethane (H3CiCH3) 143
3.6 An Introduction to π Bonds: An Example with Ethene (H2CwCH2) 145
3.7 Nonbonding Orbitals: An Example with Formaldehyde (H2CwO) 148
3.8 Triple Bonds: An Example with Ethyne (HC{CH) 149
3.9 Bond Rotation about Single and Double Bonds: Cis–Trans Isomerism 151
3.10 Strategies for Success: Molecular Models and Extended Geometry
about Single and Double Bonds 154
3.11 Hybridization, Bond Characteristics, and Effective Electronegativity 155
Problems 159
xii / Contents
Nomenclature
2 Naming Alkenes, Alkynes, and

Benzene Derivatives 163
N2.1 Alkenes and Alkynes 163
N2.2 Benzene and Benzene Derivatives 170
4 Isomerism 1
Conformational and Constitutional Isomers 176
4.1 Isomerism: A Relationship 177

4.2 Conformational Isomers: Rotational Conformations, Newman
Projections, and Dihedral Angles 177
4.3 Conformational Isomers: Energy Changes and Conformational
Analysis 180
4.4 Conformational Isomers: Cyclic Alkanes and Ring Strain 185
4.5 Conformational Isomers: The Most Stable Conformations of
Cyclohexane, Cyclopentane, Cyclobutane, and Cyclopropane 189
4.6 Conformational Isomers: Cyclopentane, Cyclohexane, Pseudorotation,
and Chair Flips 192
4.7 Strategies for Success: Drawing Chair Conformations of Cyclohexane 196
4.8 Conformational Isomers: Monosubstituted Cyclohexane 197
4.9 Conformational Isomers: Disubstituted Cyclohexanes, Cis and Trans
Isomers, and Haworth Projections 201
4.10 Strategies for Success: Molecular Modeling Kits and Chair Flips 203
4.11 Constitutional Isomerism: Identifying Constitutional Isomers 203
4.12 Constitutional Isomers: Index of Hydrogen Deficiency (Degree
of Unsaturation) 206
4.13 Strategies for Success: Drawing All Constitutional Isomers of a Given
Formula 209
4.15 Constitutional Isomers and Biomolecules: Amino Acids
and Monosaccharides 213
4.16 Saturation and Unsaturation in Fats and Oils 215

Problems 217
5 Isomerism 2
Chirality, Enantiomers, and Diastereomers 224
5.1 Defining Configurational Isomers,

Enantiomers, and Diastereomers 225
5.2 Enantiomers, Mirror Images, and
Superimposability 226
Contents / xiii
5.3 Strategies for Success: Drawing Mirror Images 228
5.4 Chirality 230
5.5 Diastereomers 242
5.6 Fischer Projections and Stereochemistry 246
5.7 Strategies for Success: Converting between Fischer Projections and
Zigzag Conformations 248
5.8 Physical and Chemical Properties of Isomers 251
5.9 Stability of Double Bonds and Chemical Properties of Isomers 255
5.10 Separating Configurational Isomers 257
5.11 Optical Activity 258
5.13 The Chirality of Biomolecules 263
5.14 The D/L System for Classifying Monosaccharides and Amino Acids 264
5.15 The D Family of Aldoses 266

Problems 268
Nomenclature
3 Considerations of Stereochemistry
R and S Configurations about Tetrahedral Stereocenters
and Z and E Configurations about Double Bonds 276
N3.1 Priority of Substituents and Stereochemical Configurations at

Tetrahedral Centers: R/S Designations 276
N3.2 Stereochemical Configurations of Alkenes: Z/E Designations 289
6 The Proton Transfer Reaction

An Introduction to Mechanisms, Thermodynamics,
and Charge Stability 295
6.1 An Introduction to Reaction Mechanisms: The Proton Transfer Reaction

and Curved Arrow Notation 296
6.2 Chemical Equilibrium and the Equilibrium Constant, Keq 298
6.3 Thermodynamics and Gibbs Free Energy 308
6.4 Strategies for Success: Functional Groups and Acidity 310
6.5 Relative Strengths of Charged and Uncharged Acids: The Reactivity
of Charged Species 312
6.6 Relative Acidities of Protons on Atoms with Like Charges 314
6.7 Strategies for Success: Ranking Acid and Base Strengths—
The Relative Importance of Effects on Charge 329
6.8 Strategies for Success: Determining Relative Contributions by
Resonance Structures 333
xiv / Contents
6.10 The Structure of Amino Acids in Solution as a Function
of pH 336
6.11 Electrophoresis and Isoelectric Focusing 339

Problems 343
7 An Overview of the Most Common

Elementary Steps 351
7.1 Mechanisms as Predictive Tools: The Proton Transfer Step
Revisited 352
7.2 Bimolecular Nucleophilic Substitution (SN2) Steps 356
7.3 Bond-Formation (Coordination) and Bond-Breaking
(Heterolysis) Steps 359
7.4 Bimolecular Elimination (E2) Steps 361
7.5 Nucleophilic Addition and Nucleophile Elimination Steps 362
7.6 Electrophilic Addition and Electrophile Elimination Steps 365
7.7 Carbocation Rearrangements: 1,2-Hydride Shifts and 1,2-Alkyl
Shifts 368
7.8 The Driving Force for Chemical Reactions 370
7.9 Keto–Enol Tautomerization 373
Problems 379
Interchapter
1 Molecular Orbital Theory and

Chemical Reactions 388
IC1.1 An Overview of Frontier Molecular Orbital Theory 388
IC1.2 Proton Transfer Steps 390
IC1.3 Bimolecular Nucleophilic Substitution (SN2) Steps 391
IC1.4 Bond-Formation (Coordination) and Bond-Breaking
(Heterolysis) Steps 392
IC1.5 Bimolecular Elimination (E2) Steps 393
IC1.6 Nucleophilic Addition and Nucleophile Elimination Steps 395
IC1.7 Electrophilic Addition and Electrophile Elimination Steps 396
IC1.8 Carbocation Rearrangements 397
Problems 397
Contents / xv
Nomenclature
4 Naming Compounds with Common

Functional Groups
Alcohols, Amines, Ketones, Aldehydes, Carboxylic
Acids, Acid Halides, Acid Anhydrides, Nitriles,
and Esters 398
N4.1 The Basic System for Naming Carboxylic Acids, Acid Anydrides,
Esters, Acid Chlorides, Amides, Nitriles, Aldehydes, Ketones,
Alcohols, and Amines 398
N4.2 Substituents in Compounds with Functional Groups That Call for a
Suffix 403
N4.3 Naming Compounds That Have an Alkene or Alkyne Group as Well as a
Functional Group That Calls for a Suffix 406
N4.4 Stereochemistry and Functional Groups That Require a Suffix 408
N4.5 The Hierarchy of Functional Groups 410
N4.6 Trivial Names Involving Functional Groups That Call for a Suffix 412
8 An Introduction to Multistep
Mechanisms
SN1 and E1 Reactions 420
8.1 The Unimolecular Nucleophilic Substitution (SN1) Reaction 421

8.2 The Unimolecular Elimination (E1) Reaction 425
8.3 Direct Experimental Evidence for Reaction Mechanisms 427
8.4 The Kinetics of SN2, SN1, E2, and E1 Reactions 427
8.5 Stereochemistry of Nucleophilic Substitution and Elimination
Reactions 433
8.6 Proton Transfers and Carbocation Rearrangements as Part of Multistep
Mechanisms: The Reasonableness of a Mechanism 446
Problems 457
9 Nucleophilic Substitution and

Elimination Reactions 1
Competition among SN2, SN1, E2, and E1 Reactions 466
9.1 The Competition among SN2, SN1, E2, and E1 Reactions 467
9.2 Rate-Determining Steps Revisited: Simplified Pictures of the SN2, SN1,
E2, and E1 Reactions 469
9.3 Factor 1: Strength of the Attacking Species 471
xvi / Contents
9.4 Factor 2: Concentration of the Attacking Species 480
9.5 Factor 3: Leaving Group Ability 482
9.6 Factor 4: Type of Carbon Bonded to the Leaving Group 487
9.7 Factor 5: Solvent Effects 493
9.8 Factor 6: Heat 498
9.9 Predicting the Outcome of Nucleophilic Substitution and Elimination
Reactions 499
9.10 Regioselectivity in Elimination Reactions: Zaitsev’s Rule 504
9.11 Intermolecular Reactions versus Intramolecular Cyclizations 507
9.12 Kinetic Control, Thermodynamic Control, and Reversibility 508
9.14 Nucleophilic Substitution Reactions and Monosaccharides:
The Formation and Hydrolysis of Glycosides 512

Reaction Tables 516
Problems 517
10 Nucleophilic Substitution and

Elimination Reactions 2
Reactions That Are Useful for Synthesis 524
10.1 Nucleophilic Substitution: Converting Alcohols to Alkyl Halides Using

PBr3 and PCl3 525
10.2 Nucleophilic Substitution: Alkylation of Ammonia and Amines 529
10.3 Nucleophilic Substitution: Alkylation of α Carbons 531
10.4 Nucleophilic Substitution: Halogenation of α Carbons 536
10.5 Nucleophilic Substitution: Diazomethane Formation of Methyl
Esters 541
10.6 Nucleophilic Substitution: Formation of Ethers and Epoxides 543
10.7 Nucleophilic Substitution: Epoxides and Oxetanes as
Substrates 547
10.8 Elimination: Generating Alkynes via Elimination Reactions 555
10.9 Elimination: Hofmann Elimination 558
Reaction Tables 562
Problems 564
Contents / xvii
11 Electrophilic Addition to
Nonpolar ě Bonds 1
Addition of a Brønsted Acid 570
11.1 The General Electrophilic Addition Mechanism: Addition of a Strong

Brønsted Acid to an Alkene 571
11.2 Benzene Rings Do Not Readily Undergo Electrophilic Addition
of Brønsted Acids 574
11.3 Regiochemistry: Production of the More Stable Carbocation
and Markovnikov’s Rule 575
11.4 Carbocation Rearrangements 579
11.5 Stereochemistry 581
11.6 Addition of a Weak Acid: Acid Catalysis 583
11.7 Electrophilic Addition of a Strong Brønsted Acid to an Alkyne 585
11.8 Acid-Catalyzed Hydration of an Alkyne: Synthesis of a Ketone 589
11.9 Electrophilic Addition of a Brønsted Acid to a Conjugated Diene:
1,2-Addition and 1,4-Addition 592
11.10 Kinetic versus Thermodynamic Control in Electrophilic Addition
to a Conjugated Diene 595
11.12 Terpene Biosynthesis: Carbocation Chemistry in Nature 598

Reaction Table 604
Problems 605
12 Electrophilic Addition to
Nonpolar ě Bonds 2
Reactions Involving Cyclic Transition States 610
12.1 Electrophilic Addition via a Three-Membered Ring:

The General Mechanism 611
12.2 Electrophilic Addition of Carbenes: Formation of Cyclopropane Rings 613
12.3 Electrophilic Addition Involving Molecular Halogens: Synthesis
of 1,2-Dihalides and Halohydrins 616
12.4 Oxymercuration–Reduction: Addition of Water 623
12.5 Epoxide Formation Using Peroxyacids 627
12.6 Hydroboration–Oxidation: Anti-Markovnikov Syn Addition of Water to an
Alkene 630
12.7 Hydroboration–Oxidation of Alkynes 637
Reaction Tables 639
Problems 640
xviii / Contents
13 Organic Synthesis 1
Beginning Concepts 645
13.1 Writing the Reactions of an Organic Synthesis 646

13.2 Cataloging Reactions: Functional Group Transformations and
Carbon–Carbon Bond Formation/Breaking Reactions 650
13.3 Retrosynthetic Analysis: Thinking Backward to Go Forward 652
13.4 Synthetic Traps 656
13.5 Choice of the Solvent 662
13.6 Considerations of Stereochemistry in Synthesis 664
13.7 Percent Yield 668
Problems 671
14 Orbital Interactions 2
Extended ě Systems, Conjugation, and
Aromaticity 676
14.1 The Shortcomings of VB Theory 677

14.2 Multiple-Center MOs 680
14.3 Aromaticity and Hückel’s Rules 688
14.4 The MO Picture of Benzene: Why It’s Aromatic 692
14.5 The MO Picture of Cyclobutadiene: Why It’s Antiaromatic 694
14.6 Aromaticity in Larger Rings: [n]Annulenes 697
14.7 Aromaticity and Multiple Rings 698
14.8 Heterocyclic Aromatic Compounds 699
14.9 Aromatic Ions 700
14.10 Strategies for Success: Counting ě Systems and ě Electrons Using
the Lewis Structure 701
14.12 Aromaticity and DNA 706

Problems 709
15 Structure Determination 1
Ultraviolet-Visible and Infrared
Spectroscopies 715
15.1 An Overview of Ultraviolet-Visible Spectroscopy 716

15.2 The UV-Vis Spectrum: Photon Absorption and
Electron Transitions 718
15.3 Effects of Structure on lmax 721
Contents / xix
15.4 IR Spectroscopy 726
15.5 A Closer Look at Some Important Absorption Bands 734
15.6 Structure Elucidation Using IR Spectroscopy 744
Problems 750
16 Structure Determination 2
Nuclear Magnetic Resonance Spectroscopy
and Mass Spectrometry 757
16.1 NMR Spectroscopy: An Overview 758

16.2 Nuclear Spin and the NMR Signal 759
16.3 Shielding, Chemical Distinction, and the Number of NMR Signals 761
16.4 Strategies for Success: The Chemical Distinction Test and Molecular
Symmetry 764
16.5 The Time Scale of NMR Spectroscopy 766
16.6 Chemical Shift 768
16.7 Characteristic Chemical Shifts, Inductive Effects, and Magnetic
Anisotropy 769
16.8 Trends in Chemical Shift 773
16.9 Integration of Signals 774
16.10 Splitting of the Signal by Spin–Spin Coupling: The N + 1 Rule 776
16.11 Coupling Constants and Spectral Resolution 780
16.12 Complex Signal Splitting 784
13
16.13 C NMR Spectroscopy 787
16.14 DEPT 13C NMR Spectroscopy 791
16.15 Structure Elucidation Using NMR Spectroscopy 793
16.16 Mass Spectrometry: An Overview 797
16.17 Features of a Mass Spectrum: Fragmentation 798
16.18 Isotope Effects: M + 1 and M + 2 Peaks 800
16.19 Determining a Molecular Formula from the Mass Spectrum 803
Problems 806
17 Nucleophilic Addition to Polar ě Bonds 1

Addition of Strong Nucleophiles 815
17.1 An Overview of the General Mechanism: Addition of Strong

Nucleophiles 816
17.2 Substituent Effects: Relative Reactivity of Ketones and Aldehydes in
Nucleophilic Addition 819
17.3 Hydride Reducing Agents: LiAlH4 and NaBH4 821
xx / Contents
17.4 Sodium Hydride: A Strong Base but a Poor Nucleophile 825
17.5 Reactions of Organometallic Compounds: Alkyllithium Reagents and
Grignard Reagents 827
17.6 Limitations of Alkyllithium and Grignard Reagents 830
17.7 Wittig Reagents and the Wittig Reaction: Synthesis of Alkenes 831
17.8 Generating Wittig Reagents 833
17.9 Sulfonium Ylides: Formation of Epoxides 835
17.10 Direct Addition versus Conjugate Addition 837
17.11 Lithium Dialkylcuprates and the Selectivity of Organometallic
Reagents 843
17.12 Organic Synthesis: Grignard and Alkyllithium Reactions in
Synthesis 846
17.13 Organic Synthesis: Considerations of Direct Addition versus
Conjugate Addition 848
17.14 Organic Synthesis: Considerations of Regiochemistry in the
Formation of Alkenes 850
Reaction Tables 852
Problems 854
18 Nucleophilic Addition to Polar π Bonds 2

Weak Nucleophiles and Acid and Base Catalysis 861
18.1 Addition of Weak Nucleophiles: Acid and Base Catalysis 862

18.2 Formation and Hydrolysis Reactions Involving Acetals, Imines,
Enamines, and Nitriles 869
18.3 The Wolff–Kishner Reduction 877
18.4 Enolate Nucleophiles: Aldol and Aldol-Type Additions 879
18.5 Aldol Condensations 882
18.6 Aldol Reactions Involving Ketones 884
18.7 Crossed Aldol Reactions 886
18.8 Intramolecular Aldol Reactions 891
18.9 Aldol Additions Involving Nitriles and Nitroalkanes 894
18.10 The Robinson Annulation 896
18.11 Organic Synthesis: Aldol Reactions in Synthesis 898
18.12 Organic Synthesis: Imagining an Alternate Target Molecule in a
Retrosynthetic Analysis 900
18.14 Ring Opening and Closing of Monosaccharides; Mutarotation 902

Reaction Tables 907
Problems 909
Contents / xxi
19 Organic Synthesis 2
Intermediate Topics in Synthesis Design, and Useful
Reduction and Oxidation Reactions 919
19.1 Umpolung in Organic Synthesis: Forming Bonds between Carbon Atoms
Initially Bearing Like Charge; Making Organometallic Reagents 920
19.2 Relative Positioning of Functional Groups in Carbon–Carbon
Bond-Formation Reactions 923
19.3 Reactions That Remove a Functional Group Entirely from
a Molecule: Reductions of C w O to CH2 927
19.4 Avoiding Synthetic Traps: Selective Reagents
and Protecting Groups 931
19.5 Catalytic Hydrogenation 941
19.6 Oxidations of Alcohols and Aldehydes 947
Reaction Table 954
Problems 955
20 Nucleophilic Addition–Elimination
Reactions 1
The General Mechanism Involving Strong
Nucleophiles 962
20.1 An Introduction to Nucleophilic Addition–Elimination Reactions:
Base-Promoted Transesterification 963
20.2 Reaction of an Ester with Hydroxide (Saponification) and the Reverse
Reaction 968
20.3 Acyl Substitution Involving Other Carboxylic Acid Derivatives: The
Thermodynamics of Acyl Substitution 971
20.4 Carboxylic Acids from Amides; the Gabriel Synthesis of Primary
Amines 975
20.5 Haloform Reactions 979
20.6 Hydride Reducing Agents: Sodium Borohydride (NaBH4) and Lithium
Aluminum Hydride (LiAlH4) 982
20.7 Specialized Reducing Agents: Diisobutylaluminum Hydride (DIBAH)
and Lithium Tri-tert-butoxyaluminum Hydride 990
20.8 Organometallic Reagents 993
Reaction Tables 998
Problems 1000
21 Nucleophilic Addition–Elimination
Reactions 2
Weak Nucleophiles 1006
21.1 The General Nucleophilic Addition–Elimination Mechanism Involving

Weak Nucleophiles: Alcoholysis and Hydrolysis of Acid Chlorides 1007
xxii / Contents
21.2 Relative Reactivities of Acid Derivatives: Rates of Hydrolysis 1010
21.3 Aminolysis of Acid Derivatives 1014
21.4 Synthesis of Acid Halides: Getting to the Top of the Stability Ladder 1016
21.5 The Hell–Volhard–Zelinsky Reaction: Synthesizing α-Bromo
Carboxylic Acids 1019
21.6 Sulfonyl Chlorides: Synthesis of Mesylates, Tosylates, and Triflates 1021
21.7 Base and Acid Catalysis in Nucleophilic Addition–Elimination
Reactions 1023
21.8 Baeyer–Villiger Oxidations 1028
21.9 Claisen Condensations 1030
21.10 Organic Synthesis: Decarboxylation, the Malonic Ester Synthesis,
and the Acetoacetic Ester Synthesis 1040
21.11 Organic Synthesis: Protecting Carboxylic Acids and Amines 1044
21.13 Determining a Protein’s Primary Structure via Amino Acid
Sequencing: Edman Degradation 1046
21.14 Synthesis of Peptides 1049

Reaction Tables 1053
Problems 1055
22 Electrophilic Aromatic Substitution 1

Substitution on Benzene; Useful Accompanying
Reactions 1065
22.1 The General Mechanism of Electrophilic Aromatic Substitutions 1067
22.2 Halogenation 1069
22.3 Friedel–Crafts Alkylation 1072
22.4 Limitations of Friedel–Crafts Alkylations 1075
22.5 Friedel–Crafts Acylation 1077
22.6 Nitration 1080
22.7 Sulfonation 1082
22.8 Organic Synthesis: Considerations of Carbocation Rearrangements
and the Synthesis of Primary Alkylbenzenes 1084
22.9 Organic Synthesis: Common Reactions Used in Conjunction
with Electrophilic Aromatic Substitution Reactions 1085
Problems 1096
23 Electrophilic Aromatic Substitution 2

Substitution on Mono- and Disubstituted Benzene and
Other Aromatic Rings 1104
23.1 Regiochemistry of Electrophilic Aromatic Substitution: Identifying
Ortho/Para and Meta Directors 1105
Contents / xxiii
23.2 Nitration of Phenol: Why Is a Hydroxyl Group an
Ortho/Para Director? 1107
23.3 Nitration of Toluene: Why Is CH3 an Ortho/Para Director? 1110
23.4 Nitration of Nitrobenzene: Why Is NO2 a Meta Director? 1112
23.5 The Activation and Deactivation of Benzene toward Electrophilic
Aromatic Substitution 1114
23.6 The Impacts of Substituent Effects on the Outcomes of Electrophilic
Aromatic Substitution Reactions 1118
23.7 The Impact of Reaction Conditions on Substituent Effects 1121
23.8 Electrophilic Aromatic Substitution on Disubstituted Benzenes 1123
23.9 Electrophilic Aromatic Substitution Involving Aromatic Rings Other
Than Benzene 1126
23.10 Nucleophilic Aromatic Substitution Mechanisms 1130
23.11 Organic Synthesis: Considerations of Regiochemistry; Attaching
Groups in the Correct Order 1135
23.12 Organic Synthesis: Interconverting Ortho/Para and
Meta Directors 1137
23.13 Organic Synthesis: Considerations of Protecting Groups 1139
Reaction Table 1143
Problems 1144
24 The Diels–Alder Reaction and

Other Pericyclic Reactions 1154
24.1 Curved Arrow Notation and Examples 1155
24.2 Conformation of the Diene 1159
24.3 Substituent Effects on the Driving Force 1162
24.4 Stereochemistry of Diels–Alder Reactions 1163
24.5 Regiochemistry of Diels–Alder Reactions 1168
24.6 The Reversibility of Diels–Alder Reactions; the Retro Diels–Alder
Reaction 1171
24.7 Syn Dihydroxylation of Alkenes and Alkynes Using OsO4 or KMnO4 1173
24.8 Oxidative Cleavage of Alkenes and Alkynes 1175
24.9 Organic Synthesis: The Diels–Alder Reaction in Synthesis 1181
24.10 A Molecular Orbital Picture of the Diels–Alder Reaction 1182
Problems 1191
25 Reactions Involving Free Radicals 1199
25.1 Homolysis: Curved Arrow Notation and Radical Initiators 1200

25.2 Structure and Stability of Alkyl Radicals 1205
xxiv / Contents
25.3 Common Elementary Steps That Free Radicals Undergo 1210
25.4 Radical Halogenation of Alkanes: Synthesis of Alkyl Halides 1213
25.5 Radical Addition of HBr: Anti-Markovnikov Addition 1226
25.6 Stereochemistry of Free-Radical Halogenation and HBr Addition 1228
25.7 Dissolving Metal Reductions: Hydrogenation of Alkenes and Alkynes 1229
25.8 Organic Synthesis: Radical Reactions in Synthesis 1234
Reaction Table 1238
Problems 1238
Interchapter
2 Fragmentation Pathways in
Mass Spectrometry 1245
IC2.1 Alkanes 1246
IC2.2 Alkenes and Aromatic Compounds 1248
IC2.3 Alkyl Halides, Amines, Ethers, and Alcohols 1250
IC2.4 Carbonyl-Containing Compounds 1253
26 Polymers 1255
26.1 Polystyrene: A Synthetic Polymer 1256

26.2 General Aspects of Polymers 1266
26.3 Other Polymerization Reactions 1275
26.4 Chemical Reactions after Polymerization 1280
26.5 Properties of Polymers 1285
26.6 Uses of Polymers: The Relationship between Structure and Function in
Materials for Food Storage 1291
26.7 Degradation and Depolymerization 1294
26.8 Biological Macromolecules 1296

Problems 1304
Appendix A Values of Ka and pKa for Various Acids A-1

Appendix B Characteristic Reactivities of Particular Functional Groups A-4
Appendix C Reactions That Alter the Carbon Skeleton A-9
Appendix D Synthesizing Particular Functional Groups via Functional Group
Transformations A-13
Glossary G–1
Answers to Your Turns AN–1
Art Credits C–1
Index I–1
Contents / xxv
List of Interest Boxes
Chemistry with Chicken Wire 5
Turning an Inorganic Surface into an Organic Surface 11
Room Temperature Ionic Liquids 97
Enzyme Active Sites: The Lock-and-Key Model 107
Phase Transfer Catalysts 112
Quantum Teleportation 131
Freezing Point Elevation? 157
An All-Gauche Alkane 186
Cubane: A Useful “Impossible” Compound? 194
Nanocars 241
Circular Dichroism 262
Caution: Hydrofluoric Acid Is a Weak Acid 307
Superacids: How Strong Can an Acid Be? 328
“Watching” a Bond Break 369
Sugar Transformers 376
Phosphorylation: An Enzyme’s On/Off Switch 445
Using Proton Transfer Reactions to Discover New Drugs 452
Rotaxanes: Exploiting Steric Hindrance 493
You Can’t Always Want What You Get: How an Enzyme Can Manipulate
the Reactivity of a Substrate 497
DNA Alkylation: Cancer Causing and Cancer Curing 554
Mechanically Generated Acid and Self-Healing Polymers 561
Electrophilic Addition and Laser Printers 579
Kinetic Control, Thermodynamic Control, and Mad Cow Disease 598
Halogenated Metabolites: True Sea Treasures 623
Benzo[a]pyrene: Smoking, Epoxidation, and Cancer 631
Conjugated Linoleic Acids 689
Benzene and Molecular Transistors 696
The Chemistry of Vision 725
IR Spectroscopy and the Search for Extraterrestrial Life 744
Magnetic Resonance Imaging 787
Mass Spectrometry, CSI, and ER 805
NADH as a Biological Hydride Reducing Agent 825
Michael Addition in the Fight against Cancer 842
Hypoglycemia and Aldol Reactions 891
Protecting Groups in DNA Synthesis 940
xxvii
Chromic Acid Oxidation and the BreathalyzerTM Test 951
Biodiesel and Transesterification 967
The Stability Ladder in Biochemical Systems 974
Biological Claisen Condensations 1039
Aromatic Sulfonation: Antibiotics and Detergents 1083
Sodium Nitrite and Foods: Preventing Botulism but Causing
Cancer? 1091
Iodized Salt and Electrophilic Aromatic Substitution 1110
2,4,6-Trinitrotoluene (TNT) 1119
Biological Diels–Alder Reactions 1158
Ethene, KMnO4, and Fruit Ripening 1180
Halogenated Alkanes and the Ozone Layer 1218
Free Radicals in the Body: Lipid Peroxidation and Vitamin E 1225
Stereochemistry, Polypropylene, and the Nobel Prize 1274
What Happens to Recycled Plastic? 1296
xxviii / List of Interest Boxes

List of Mechanisms
General SN2 mechanism (Equation 8-1) 421
General SN1 mechanism (Equation 8-2) 421
General E2 mechanism (Equation 8-4) 425
General E1 mechanism (Equation 8-5) 425
SN2 mechanism under basic conditions (Equation 8-28) 447
SN1 mechanism under acidic conditions (Equation 8-31) 449
SN1 mechanism with a carbocation rearrangement
(Equation 8-38) 454
Competition among SN2, SN1, E2, and E1 mechanisms
(Equations 9-1 through 9-4) 468
Acid-catalyzed dehydration of an alcohol (Equation 9-26) 486
Solvolysis of an alkyl halide (Equations 9-38 and 9-39) 502
Acid-catalyzed glycoside formation of a sugar (Equation 9-54) 513
Acid-catalyzed bromination of an alcohol (Equation 10-2) 525
PBr3 bromination of an alcohol (Equation 10-8) 527
Alkylation of an amine (Equation 10-13) 530
Alkylation of an α carbon of a ketone or aldehyde
(Equation 10-19) 532
Halogenation of an α carbon of a ketone or aldehyde under basic
conditions (Equation 10-27) 537
Polyhalogenation of an α carbon of a ketone or aldehyde under basic
Halogenation of an α carbon of a ketone or aldehyde under acidic
Diazomethane formation of a methyl ester (Equation 10-33) 542
Williamson ether synthesis (Equation 10-36) 544
Formation of a cyclic ether from a haloalcohol under basic conditions
Formation of a symmetric ether from an alcohol under acidic conditions
Ring opening of an epoxide under basic conditions
Ring opening of an unsymmetric epoxide under basic conditions
Ring opening of an unsymmetric epoxide under acidic conditions
Formation of a terminal alkyne from a vinyl halide
xxix
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Organic Chemistry Principles and

Mechanisms 1st Edition Joel Karty

Organic chemistry principles and mechanisms Second

Get ready for organic chemistry Karty

Electron Flow in Organic Chemistry A Decision Based

March's Advanced Organic Chemistry: Reactions,

Practical Synthetic Organic Chemistry Reactions

Organic Chemistry John Mcmurry

Organic Chemistry Jonathan Clayden

Chemistry³ Introducing inorganic organic and physical

Copyright © 2014 by W. W. Norton & Company, Inc.

All rights reserved.

Editor: Erik Fahlgren

Library of Congress Cataloging-in-Publication Data has been applied for.

1 Atomic and Molecular Structure 1

1.1 What Is Organic Chemistry? 2

Chapter Summary and Key Terms 47

1 Introduction: The Basic System for

N1.1 The Need for Systematic Nomenclature: An Introduction to the IUPAC

Chapter Summary and Key Terms 120

3.1 Atomic Orbitals and the Wave Nature of Electrons 129

2 Naming Alkenes, Alkynes, and

4.1 Isomerism: A Relationship 177

Chapter Summary and Key Terms 216

5.1 Defining Configurational Isomers,

Chapter Summary and Key Terms 268

N3.1 Priority of Substituents and Stereochemical Configurations at

6 The Proton Transfer Reaction

6.1 An Introduction to Reaction Mechanisms: The Proton Transfer Reaction

Chapter Summary and Key Terms 342

7 An Overview of the Most Common

1 Molecular Orbital Theory and

4 Naming Compounds with Common

8.1 The Unimolecular Nucleophilic Substitution (SN1) Reaction 421

9 Nucleophilic Substitution and

Chapter Summary and Key Terms 515

10 Nucleophilic Substitution and

10.1 Nucleophilic Substitution: Converting Alcohols to Alkyl Halides Using

11.1 The General Electrophilic Addition Mechanism: Addition of a Strong

Chapter Summary and Key Terms 603

12.1 Electrophilic Addition via a Three-Membered Ring:

13.1 Writing the Reactions of an Organic Synthesis 646

14.1 The Shortcomings of VB Theory 677

Chapter Summary and Key Terms 708

15.1 An Overview of Ultraviolet-Visible Spectroscopy 716

16.1 NMR Spectroscopy: An Overview 758

17 Nucleophilic Addition to Polar ě Bonds 1

17.1 An Overview of the General Mechanism: Addition of Strong

18 Nucleophilic Addition to Polar π Bonds 2

18.1 Addition of Weak Nucleophiles: Acid and Base Catalysis 862

Chapter Summary and Key Terms 906

21.1 The General Nucleophilic Addition–Elimination Mechanism Involving

Chapter Summary and Key Terms 1052

22 Electrophilic Aromatic Substitution 1

23 Electrophilic Aromatic Substitution 2

24 The Diels–Alder Reaction and

25 Reactions Involving Free Radicals 1199

25.1 Homolysis: Curved Arrow Notation and Radical Initiators 1200

26.1 Polystyrene: A Synthetic Polymer 1256

26.9 Wrapping Up and Looking Ahead 1302

Appendix A Values of Ka and pKa for Various Acids A-1

xxviii / List of Interest Boxes

K. F. Koehler, Verlag, Leipzig