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E-book: Organic Chemistry: Principles and Mechanisms (Third Edition)

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(Elon University)
  • Format: 1672 pages
  • Pub. Date: 01-Aug-2022
  • Publisher: WW Norton & Co
  • Language: eng
  • ISBN-13: 9780393877465
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Organic Chemistry: Principles and Mechanisms (Third Edition)Larger Image
  • Format: 1672 pages
  • Pub. Date: 01-Aug-2022
  • Publisher: WW Norton & Co
  • Language: eng
  • ISBN-13: 9780393877465
Other books in subject:

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"Joel Karty doesn't just think that students benefit from a mechanistic approach-he can prove it. With the third edition, Joel brings organic chemistry to life through a new series of student-focused videos on mastering mechanisms and succeeding in the course. Furthermore, Joel has brought more active-learning into the text, including a new two-column solved problem format that helps promote understanding over memorization, and in-text features that challenge students to apply new concepts just after reading about them"--

Motivate every student to think about, practice, and apply organic chemistry.

Joel Karty's text helps students succeed in organic chemistry, and our adopters overwhelmingly agree that his mechanistically organized approach works. The Third Edition includes a new video series that models the critical thinking skills that students need to master. Redesigned, two-column Solved Problems then coach students in applying those critical thinking skills to solving chemical equations, which helps them avoid overreliance on memorization. Interactive features in the ebook and Smartwork consistently give students opportunities to practice what they’ve learned.

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List of Biochemistry Topics
xxix
List of Interest Boxes
xxx
List of Connections Boxes
xxxi
List of Green Chemistry Boxes
xxxiii
List of Mechanisms
xxxiv
Preface xxxviii
1 Atomic and Molecular Structure
1(51)
1.1 What Is Organic Chemistry?
1(2)
1.2 Why Carbon?
3(1)
1.3 Atomic Structure and Ground State Electron Configurations
4(4)
1.4 The Covalent Bond: Bond Energy and Bond Length
8(3)
1.5 Lewis Dot Structures and the Octet Rule
11(3)
1.6 Strategies for Success: Drawing Lewis Dot Structures Quickly
14(1)
1.7 Electronegativity, Polar Covalent Bonds, and Bond Dipoles
15(3)
1.8 Ionic Bonds
18(2)
1.9 Assigning Electrons to Atoms in Molecules: Formal Charge
20(1)
1.10 Resonance Theory
21(5)
1.11 Strategies for Success: Drawing All Resonance Structures
26(4)
1.12 Shorthand Notations
30(3)
1.13 An Overview of Organic Compounds: Functional Groups
33(4)
The Organic Chemistry of Biomolecules
1.14 An Introduction to Proteins, Carbohydrates, and Nucleic Acids: Fundamental Building Blocks and Functional Groups
37(15)
Chapter Summary and Key Terms
44(1)
Problems
44(8)
INTERCHAPTER
A Nomenclature: The Basic System for Naming Organic Compounds Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes, and Ethers
52(16)
A.1 The Need for Systematic Nomenclature: An Introduction to the IUPAC System
52(1)
A.2 Alkanes and Substituted Alkanes
53(2)
A.3 Haloalkanes and Nitroalkanes: Roots, Prefixes, and Locator Numbers
55(4)
A.4 Alkyl Substituents: Branched Alkanes and Substituted Branched Alkanes
59(2)
A.5 Cyclic Alkanes and Cyclic Alkyl Groups
61(2)
A.6 Ethers and Alkoxy Groups
63(1)
A.7 Trivial Names or Common Names
64(1)
Problems
65(3)
2 Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties
68(44)
2.1 Valence Shell Electron Pair Repulsion (VSEPR) Theory: Three-Dimensional Geometry
69(4)
2.2 Dash--Wedge Notation
73(2)
2.3 Strategies for Success: The Molecular Modeling Kit
75(1)
2.4 Net Molecular Dipoles
76(1)
2.5 Physical Properties, Functional Groups, and Intermolecular Interactions
77(2)
2.6 Melting Points, Boiling Points, and Intermolecular Interactions
79(8)
2.7 Solubility
87(5)
2.8 Strategies for Success: Ranking Boiling Points and Solubilities of Structurally Similar Compounds
92(4)
2.9 Protic and Aprotic Solvents
96(2)
The Organic Chemistry of Biomolecules
2.10 An Introduction to Lipids
98(14)
Chapter Summary and Key Terms
104(1)
Problems
105(7)
3 Valence Bond Theory and Molecular Orbital Theory
112(38)
3.1 An Introduction to Valence Bond Theory and σ Bonds: An Example with H2
113(2)
3.2 Valence Bond Theory and Tetrahedral Electron Geometry: Alkanes and sp3 Hybridization
115(3)
3.3 Valence Bond Theory and Lone Pairs of Electrons
118(2)
3.4 Valence Bond Theory and Trigonal Planar Electron Geometry: Double Bonds, sp2 Hybridization, it Bonds, and Carbocations
120(4)
3.5 Valence Bond Theory and Linear Electron Geometry: Triple Bonds and sp Hybridization
124(3)
3.6 Strategies for Success: Quickly Identifying Hybridization and the Number of σ and π Bonds from a Lewis Structure
127(2)
3.7 Bond Rotations about Single and Double Bonds: Cis and Trans Configurations
129(3)
3.8 Strategies for Success: Molecular Modeling Kits, Bond Rotations, and Extended Geometries
132(1)
3.9 Hybridization, Bond Characteristics, and Effective Electronegativity
133(3)
3.10 A Deeper Look: Molecular Orbital Theory and the Wave Nature of Electrons
136(4)
3.11 A Deeper Look: Hybrid Atomic Orbitals and a Combined Molecular Orbital-Valence Bond Model
140(10)
Chapter Summary and Key Terms
145(1)
Problems
146(4)
INTERCHAPTER
B Naming Alkenes, Alkynes, and Benzene Derivatives
150(12)
B.1 Alkenes, Alkynes, Cycloalkenes, and Cycloalkynes: Molecules with One C C or C C Bond
150(3)
B.2 Molecules with Multiple C C or C C Bonds
153(2)
B.3 Benzene and Benzene Derivatives
155(3)
Problems
158(4)
4 Isomerism 1 Conformers and Constitutional Isomers
162(43)
4.1 Conformers: Rotational Conformations, Newman Projections, and Dihedral Angles
163(2)
4.2 Conformers: Energy Changes and Conformational Analysis
165(5)
4.3 Conformers: Ring Strain and the Most Stable Conformations of Cyclic Alkanes
170(3)
4.4 A Deeper Look: Calculating Ring Strain from Heats of Combustion
173(2)
4.5 Conformers: Cyclohexane and Chair Flips
175(2)
4.6 Strategies for Success: Drawing Chair Conformations of Cyclohexane
177(2)
4.7 Conformers: Monosubstituted Cyclohexanes
179(3)
4.8 Conformers: Disubstituted Cyclohexanes, Cis and Trans Isomers, and Haworth Projections
182(3)
4.9 Strategies for Success: Molecular Modeling Kits and Chair Flips
185(1)
4.10 Constitutional Isomerism: Identifying Constitutional Isomers
185(2)
4.11 Constitutional Isomers: Index of Hydrogen Deficiency (Degree of Unsaturation)
187(4)
4.12 Strategies for Success: Drawing All Constitutional Isomers of a Given Formula
191(4)
The Organic Chemistry of Biomolecules
4.13 Constitutional Isomers and Biomolecules: Amino Acids and Monosaccharides
195(1)
4.14 Saturation and Unsaturation in Fats and Oils
196(9)
Chapter Summary and Key Terms
198(1)
Problems
199(6)
5 Isomerism 2 Chirality, Enantiomers, and Diastereomers
205(59)
5.1 Defining Configurational Isomers, Enantiomers, and Diastereomers
205(2)
5.2 Enantiomers, Mirror Images, and Superimposability
207(2)
5.3 Strategies for Success: Drawing Mirror Images
209(2)
5.4 Chirality and the Plane of Symmetry Test
211(2)
5.5 Chiral Centers
213(6)
5.6 Absolute Stereochemical Configurations: R/S Designations of Chiral Centers
219(6)
5.7 Mirror Images That Rapidly Interconvert: Single-Bond Rotation and Nitrogen Inversion
225(3)
5.8 Diastereomers: Double-Bond Configurations and Chiral Centers
228(4)
5.9 Strategies for Success: Drawing All Stereoisomers of a Molecule with Chiral Centers
232(3)
5.10 Fischer Projections and Stereochemistry
235(2)
5.11 Strategies for Success: Converting between Fischer Projections and Zigzag Conformations
237(3)
5.12 Physical and Chemical Properties of Isomers
240(4)
5.13 Separating Configurational Isomers
244(1)
5.14 Optical Activity
245(4)
The Organic Chemistry of Biomolecules
5.15 The Chirality of Biomolecules
249(1)
5.16 The D/L System for Classifying Monosaccharides and Amino Acids
250(1)
5.17 The D Family of Aldoses
251(13)
Chapter Summary and Key Terms
253(1)
Problems
254(10)
6 The Proton Transfer Reaction An Introduction to Mechanisms, Equilibria, Free Energy Diagrams, and Charge Stability
264(54)
6.1 An Introduction to Reaction Mechanisms: The Proton Transfer Reaction and Curved Arrow Notation
265(2)
6.2 Proton Transfer Reaction Outcomes: pKa Values and Acid and Base Strengths
267(9)
6.3 A Deeper Look: Chemical Equilibrium, Equilibrium Constants, and Ka Values
276(3)
6.4 Gibbs Free Energy and the Reaction Free Energy Diagram
279(1)
6.5 A Deeper Look: Gibbs Free Energy, Equilibrium Constants, Enthalpy, and Entropy
280(2)
6.6 Functional Groups and Acidity
282(1)
6.7 Relative Strengths of Charged and Uncharged Acids: The Reactivity of Charged Species
283(2)
6.8 Relative Acidities of Protons on Atoms with Like Charges
285(14)
6.9 Strategies for Success: Ranking Acid and Base Strengths by Using the CARDIN-al Rule
299(4)
The Organic Chemistry of Biomolecules
6.10 The Structure of Amino Acids in Solution as a Function of pH
303(15)
Chapter Summary and Key Terms
306(1)
Problems
307(11)
7 An Overview of the Most Common Elementary Steps
318(42)
7.1 Mechanisms as Predictive Tools: The Proton Transfer Step Revisited
319(6)
7.2 Bimolecular Nucleophilic Substitution (SN2) Steps
325(4)
7.3 Bond-Forming (Coordination) and Bond-Breaking (Heterolysis) Steps
329(2)
7.4 Nucleophilic Addition and Nucleophile Elimination Steps
331(2)
7.5 Bimolecular Elimination (E2) Steps
333(2)
7.6 Electrophilic Addition and Electrophile Elimination Steps
335(3)
7.7 Carbocation Rearrangements: 1,2-Hydride Shifts and 1,2-Alkyl Shifts
338(1)
7.8 The Driving Force for Chemical Reactions
339(2)
7.9 Carbocations and Charge Stability
341(4)
7.10 Keto--Enol Tautomerization: An Example of Bond Energies as the Major Driving Force
345(15)
Chapter Summary and Key Terms
350(1)
Problems
351(9)
INTERCHAPTER
C Molecular Orbital Theory and Chemical Reactions
360(11)
C.1 An Overview of Frontier Molecular Orbital Theory
360(3)
C.2 Frontier Molecular Orbital Theory and Elementary Steps
363(7)
Problems
370(1)
INTERCHAPTER
D Naming Compounds with a Functional Group That Calls for a Suffix: Alcohols, Amines, Ketones, Aldehydes, Carboxylic Acids, and Carboxylic Acid Derivatives
371(22)
D.1 The Basic System for Naming Compounds with a Functional Group That: Calls for a Suffix
372(1)
D.2 Naming Alcohols and Amines
372(7)
D.3 Naming Ketones and Aldehydes
379(2)
D.4 Naming Carboxylic Acids, Acid Chlorides, Amides, and Nitriles
381(4)
D.5 Naming Esters and Acid Anhydrides
385(4)
Problems
389(4)
8 An Introduction to Multistep Mechanisms SN1 and El Reactions and Their Comparisons to SN2 and E2 Reactions
393(51)
8.1 The Unimolecular Nucleophilic Substitution (SN1) Reaction: Intermediates, Overall Reactants, and Overall Products
394(3)
8.2 The Unimolecular Elimination (El) Reaction
397(2)
8.3 The Kinetics of SN2, SN1, E2, and El Reactions: Evidence for Reaction Mechanisms
399(5)
8.4 A Deeper Look: Theoretical Rate Laws and Transition State Theory
404(2)
8.5 Stereochemistry of Nucleophilic Substitution and Elimination Reactions
406(16)
8.6 The Reasonableness of a Mechanism: Proton Transfers and Carbocation Rearrangements
422(12)
8.7 Resonance-Delocalized Intermediates in Mechanisms
434(10)
Chapter Summary and Key Terms
436(1)
Problems
436(8)
9 Competition among SN2, SN1, E2, and El Reactions
444(64)
9.1 Identifying the Competition among SN2, SN1, E2, and El Reactions
445(2)
9.2 Rate-Determining Steps Revisited: Simplified Pictures of SN2, SN1, E2, and El Reactions
447(1)
9.3 Factor 1: Strength of the Attacking Species
448(10)
9.4 Factor 2: Concentration of the Attacking Species
458(2)
9.5 Factor 3: Leaving Group Ability
460(6)
9.6 Factor 4: Type of Carbon Bonded to the Leaving Group
466(7)
9.7 Factor 5: Solvent Effects
473(6)
9.8 Factor 6: Heat
479(2)
9.9 Strategies for Success: Predicting the Outcome of an SN2/SN1/E2/E1 Competition
481(6)
9.10 Regioselectivity in Elimination Reactions: Alkene Stability and Zaitsev's Rule
487(3)
9.11 A Deeper Look: Hyperconjugation and Alkene Stability
490(1)
9.12 Intermolecular Reactions versus Intramolecular Cyclizations
491(3)
The Organic Chemistry of Biomolecules
9.13 Nucleophilic Substitution Reactions and Monosaccharides: The Formation and Hydrolysis of Glycosides
494(14)
Chapter Summary and Key Terms
497(1)
Reaction Tables
498(2)
Problems
500(8)
10 Organic Synthesis 1 Nucleophilic Substitution and Elimination Reactions and Functional Group Transformations
508(54)
10.1 The Language of Organic Synthesis
509(1)
10.2 Writing the Reactions of an Organic Synthesis
510(4)
10.3 Cataloging Reactions: Functional Group Transformations and Carbon--Carbon Bond-Forming and Bond-Breaking Reactions
514(3)
10.4 Options and Limitations in Synthesis: Ether Formation by the Williamson Synthesis and Condensation
517(6)
10.5 Converting Alcohols into Alkyl Halides: PBr3 and PCI3
523(4)
10.6 Halogenation of a Carbons
527(7)
10.7 Epoxides as Substrates
534(5)
10.8 Formation of Epoxides by Nucleophilic Substitution
539(2)
10.9 Diazomethane Formation of Methyl Esters
541(1)
10.10 Amines and Quaternary Ammonium Salts from Alkyl Halides
542(3)
10.11 Hofmann Elimination
545(3)
10.12 Generating Alkynes by Elimination Reactions
548(14)
Chapter Summary and Key Terms
551(1)
Reaction Table
552(2)
Problems
554(8)
11 Organic Synthesis 2 Reactions That Alter the Carbon Skeleton, and Designing Multistep Syntheses
562(42)
11.1 Reactions That Alter the Carbon Skeleton and Retrosynthetic Analysis
563(7)
11.2 Carbon Nucleophiles and the Opening of Epoxides
570(3)
11.3 Alkylation of a Carbons: Regioselectivity and Kinetic versus Thermodynamic Control
573(8)
11.4 Synthetic Traps
581(4)
11.5 Strategies for Success: Improving Your Proficiency with Solving Multistep Syntheses
585(2)
11.6 Green Chemistry
587(3)
11.7 A Deeper Look: Considerations of Percent Yield
590(14)
Chapter Summary and Key Terms
594(1)
Reaction Table
595(1)
Problems
596(8)
12 Electrophilic Addition to Nonpolar Bonds 1 Addition of a Brønsted Acid
604(43)
12.1 The General Electrophilic Addition Mechanism: Addition of a Strong Brønsted Acid to an Alkene
606(3)
12.2 Benzene Rings Do Not Readily Undergo Electrophilic Addition of Brønsted Acids
609(1)
12.3 Regiochemistry: Production of the More Stable Carbocation and Markovnikov's Rule
610(3)
12.4 Carbocation Rearrangements
613(2)
12.5 Stereochemistry in the Addition of a Brønsted Acid to an Alkene
615(1)
12.6 Addition of a Weak Acid: Acid Catalysis
616(4)
12.7 Electrophilic Addition of a Strong Brensted Acid to an Alkyne
620(3)
12.8 Acid-Catalyzed Hydration of an Alkyne: Synthesis of a Ketone
623(1)
12.9 Electrophilic Addition of a Brønsted Acid to a Conjugated Diene: 1,2-Addition and 1,4-Addition
624(4)
12.10 Kinetic versus Thermodynamic Control in Electrophilic Addition to a Conjugated Diene
628(3)
12.11 Organic Synthesis: Additions of Brønsted Acids to Alkenes and Alkynes
631(3)
The Organic Chemistry of Biomolecules
12.12 Terpenes and Their Biosynthesis: Carbocation Chemistry in Nature
634(13)
Chapter Summary and Key Terms
638(1)
Reaction Table
639(1)
Problems
640(7)
13 Electrophilic Addition to Nonpolar π Bonds 2 Reactions Involving Cyclic Transition States
647(46)
13.1 Electrophilic Addition via a Three-Membered Ring: The General Mechanism
648(2)
13.2 Electrophilic Addition of Carbenes: Formation of Cyclopropane Rings
650(1)
13.3 Epoxide Formation with Peroxy Acids
651(3)
13.4 Electrophilic Addition Involving Molecular Halogens: Synthesis of 1,2-Dihalides and Halohydrins
654(7)
13.5 Oxymercuration--Reduction: Addition of Water
661(6)
13.6 Hydroboration--Oxidation: Anti-Markovnikov Syn Addition of Water to an Alkene
667(7)
13.7 Hydroboration--Oxidation of Alkynes
674(1)
13.8 Organic Synthesis: Using Electrophilic Addition Reactions That Proceed through a Cyclic Transition State
675(3)
13.9 Organic Synthesis: Catalytic Hydrogenation of Alkenes and Alkynes
678(15)
Chapter Summary and Key Terms
684(1)
Reaction Tables
685(2)
Problems
687(6)
14 Conjugation and Aromaticity
693(46)
14.1 The Allyl Cation and Buta-1,3-diene: Resonance and the Conjugation of p Orbitals in Acyclic π Systems
694(4)
14.2 Isolated π Systems
698(2)
14.3 A Deeper Look: Heats of Hydrogenation and the Stability of Conjugated π Bonds
700(2)
14.4 The Allyl Anion: Conjugation and Lone Pairs of Electrons
702(2)
14.5 Cyclic π Systems: Benzene as an Aromatic Compound, and Cyclobutadiene as an Antiaromatic Compound
704(2)
14.6 A Deeper Look: Using Heats of Hydrogenation to Determine Aromaticity
706(3)
14.7 Huckel's Rules: Assessing Aromaticity Using Lewis Structures
709(6)
14.8 A Deeper Look: Molecular Orbital Theory, Conjugation, and Aromaticity
715(13)
The Organic Chemistry of Biomolecules
14.9 Aromaticity and DNA
728(11)
Chapter Summary and Key Terms
732(1)
Problems
733(6)
15 Structure Determination 1 Mass Spectrometry
739(30)
15.1 An Overview of Mass Spectrometry
740(2)
15.2 Features of a Mass Spectrum, the Nitrogen Rule, and Fragmentation
742(3)
15.3 Isotopes and Mass Spectra: M + 1 and M + 2 Peaks
745(4)
15.4 A Deeper Look: Estimating the Number of Carbon Atoms from the M + 1 Peak
749(2)
15.5 Strategies for Success: Determining a Molecular Formula from the Mass Spectrum of an Organic Compound
751(2)
15.6 A Deeper Look: Fragmentation Pathways in Mass Spectrometry
753(16)
Chapter Summary and Key Terms
764(1)
Problems
764(5)
16 Structure Determination 2 Infrared Spectroscopy and Ultraviolet-Visible Spectroscopy
769(50)
16.1 An Overview of Infrared Spectroscopy
770(2)
16.2 General Theory of Infrared Spectroscopy
772(2)
16.3 Location of Peaks in an Infrared Spectrum
774(4)
16.4 The Ball-and-Spring Model for Explaining Infrared Peak Locations
778(3)
16.5 Intensities of Peaks in an Infrared Spectrum
781(2)
16.6 Some Important Infrared Stretches
783(9)
16.7 Strategies for Success: Structure Elucidation Using Infrared Spectroscopy
792(6)
16.8 A Deeper Look: Infrared Bending Vibrations
798(2)
16.9 An Overview of Ultraviolet--Visible Spectroscopy
800(1)
16.10 Ultraviolet--Visible Spectra and Molecular Structure: Conjugation and Lone Pairs
801(5)
16.11 A Deeper Look: Molecular Orbital Theory and Ultraviolet--Visible Spectroscopy
806(13)
Chapter Summary and Key Terms
809(1)
Problems
810(9)
17 Structure Determination 3 Nuclear Magnetic Resonance Spectroscopy
819(59)
17.1 An Overview of Nuclear Magnetic Resonance Spectroscopy
819(2)
17.2 Nuclear Spin and the Nuclear Magnetic Resonance Signal
821(2)
17.3 Shielding, Chemical Distinction, and the Number of NMR Signals
823(7)
17.4 The Time Scale of Nuclear Magnetic Resonance Spectroscopy
830(1)
17.5 Characteristic Chemical Shifts, Inductive Effects, and Magnetic Anisotropy
831(4)
17.6 Strategies for Success: Predicting Approximate Chemical Shift Values
835(3)
17.7 A Deeper Look: A Quantitative Examination of the NMR Signal and Chemical Shift and a Look at Deuterated Solvents
838(2)
17.8 Integration of Signals
840(1)
17.9 Splitting of the Signal by Spin-Spin Coupling: The N + 1 Rule
841(6)
17.10 Coupling Constants and Complex Signal Splitting
847(4)
17.11 A Deeper Look: Signal Resolution and the Strength of Bext
851(2)
17.12 Carbon Signals: 13C Nuclear Magnetic Resonance Spectroscopy
853(5)
17.13 A Deeper Look: DEPT 13C NMR Spectroscopy and 2-D NMR Spectra
858(2)
17.14 Strategies for Success: Elucidating Molecular Structure Using Nuclear Magnetic Resonance Spectroscopy
860(18)
Chapter Summary and Key Terms
867(1)
Problems
868(10)
18 Nucleophilic Addition to Polar π Bonds 1 Reagents That Are Strongly Nucleophilic
878(48)
18.1 An Overview of the General Mechanism: Addition of Strong Nucleophiles
879(2)
18.2 Substituent Effects: Relative Reactivity of Ketones and Aldehydes in Nucleophilic Addition
881(2)
18.3 Reactions of Hydride Reagents: LiAIH4, NaBH4, and NaH
883(7)
18.4 Reactions of Organometallic Compounds: Alkyllithium Reagents and Grignard Reagents
890(4)
18.5 Compatibility of Functional Groups in Reactions Involving Alkyllithium and Grignard Reagents
894(1)
18.6 Wittig Reagents and the Wittig Reaction: Synthesis of Alkenes
895(2)
18.7 Generating Wittig Reagents
897(3)
18.8 Direct Addition versus Conjugate Addition
900(5)
18.9 Lithium Dialkylcuprates and the Selectivity of Organometallic Reagents
905(3)
18.10 Organic Synthesis: Grignard and Alkyllithium Reactions in Synthesis
908(2)
18.11 Organic Synthesis: Considerations of Direct Addition versus Conjugate Addition
910(2)
18.12 Organic Synthesis: Considerations of Regiochemistry in the Formation of Alkenes
912(14)
Chapter Summary and Key Terms
914(1)
Reaction Tables
915(2)
Problems
917(9)
19 Nucleophilic Addition to Polar π Bonds 2 Reagents That Are Weakly Nucleophilic or Non-nucleophilic, and Acid and Base Catalysis
926(61)
19.1 Weak Nucleophiles as Reagents: Acid and Base Catalysis
926(5)
19.2 Addition of HCN: The Formation of Cyanohydrins
931(2)
19.3 Direct Addition versus Conjugate Addition of Weak Nucleophiles and HCN
933(2)
19.4 Formation and Hydrolysis of Acetals, Imines, and Enamines
935(9)
19.5 Organic Synthesis: Synthesizing Amines via Reductive Amination
944(2)
19.6 The Wolff--Kishner Reduction
946(1)
19.7 Hydrolysis of Nitriles
947(2)
19.8 Enolate Nucleophiles: Aldol Additions
949(3)
19.9 Aldol Condensations
952(2)
19.10 Aldol Reactions Involving Ketones
954(1)
19.11 Crossed Aldol Reactions
955(6)
19.12 Intramolecular Aldol Reactions
961(4)
19.13 The Robinson Annulation
965(1)
19.14 Organic Synthesis: Aldol and Robinson Annulation Reactions in Synthesis
966(3)
The Organic Chemistry of Biomolecules
19.15 Ring Opening and Ring Closing of Monosaccharides
969(18)
Chapter Summary and Key Terms
973(1)
Reaction Tables
974(3)
Problems
977(10)
20 Redox Reactions; Organometallic Reagents and Their Reactions
987(38)
20.1 Identifying Reactions as Redox Reactions
988(4)
20.2 A Deeper Look: Calculating Oxidation States
992(2)
20.3 Catalytic Hydrogenation: A Review of Alkene and Alkyne Reductions, Reductions of Other Functional Groups, and Selectivity
994(3)
20.4 Reactions That Reduce C=O to CH2: Wolff--Kishner, Clemmensen, and Raney--Nickel Reductions
997(3)
20.5 Oxidations of Alcohols and Aldehydes
1000(5)
20.6 Generating Organometallic Reagents: Grignard Reagents, Alkyllithium Reagents, and Lithium Dialkylcuprates
1005(3)
20.7 Useful Reactions That Form Carbon-Carbon Bonds: Coupling and Alkene Metathesis Reactions
1008(17)
Chapter Summary and Key Terms
1014(1)
Reaction Tables
1015(2)
Problems
1017(8)
21 Organic Synthesis 3 Intermediate Topics in Synthesis Design
1025(26)
21.1 Considerations When a Synthesis Calls for a New Carbon--Carbon Bond
1026(9)
21.2 Avoiding Synthetic Traps: Selective Reagents and Protecting Groups
1035(16)
Chapter Summary and Key Terms
1045(1)
Problems
1045(6)
22 Nucleophilic Addition-Elimination Reactions 1 Reagents That Are Strongly Nucleophilic
1051(48)
22.1 An Introduction to Nucleophilic Addition-Elimination Reactions: Transesterification
1052(5)
22.2 Acyl Substitution Involving Other Carboxylic Acid Derivatives: The Thermodynamics of Acyl Substitution
1057(4)
22.3 Reaction of an Ester with Hydroxide (Saponification) and the Reverse Reaction
1061(2)
22.4 Carboxylic Acids from Amides; the Gabriel Synthesis of Primary Amines
1063(6)
22.5 Haloform Reactions
1069(3)
22.6 Hydride Reducing Agents: NaBH4 and LiAIH4
1072(9)
22.7 A Deeper Look: DIBAH and LTBA as Specialized Reducing Agents
1081(3)
22.8 Organometallic Reagents
1084(15)
Chapter Summary and Key Terms
1088(1)
Reaction Tables
1089(2)
Problems
1091(8)
23 Nucleophilic Addition-Elimination Reactions 2 Reagents That Are Weakly Nucleophilic or Non-nucleophilic
1099(57)
23.1 The General Nucleophilic Addition--Elimination Mechanism Involving Weak Nucleophiles: Alcoholysis and Hydrolysis of Acid Chlorides
1100(3)
23.2 Relative Reactivities of Acid Derivatives: Rates of Hydrolysis
1103(3)
23.3 Aminolysis of Acid Derivatives
1106(3)
23.4 Synthesis of Acid Halides: Getting to the Top of the Stability Ladder
1109(3)
23.5 The Hell--Volhard--Zelinsky Reaction: Synthesizing α-Bromo Carboxylic Acids
1112(2)
23.6 Sulfonyl Chlorides: Synthesis of Mesylates, Tosylates, and Triflates
1114(2)
23.7 Base and Acid Catalysis in Nucleophilic Addition--Elimination Reactions
1116(6)
23.8 Baeyer--Villiger Oxidations
1122(2)
23.9 Claisen Condensation Reactions
1124(10)
23.10 Organic Synthesis: Decarboxylation, the Malonic Ester Synthesis, and the Acetoacetic Ester Synthesis
1134(4)
The Organic Chemistry of Biomolecules
23.11 Determining the Amino Acid Sequence of a Protein
1138(18)
Chapter Summary and Key Terms
1141(1)
Reaction Tables
1142(2)
Problems
1144(12)
24 Aromatic Substitution 1 Electrophilic Aromatic Substitution on Benzene, and Useful Accompanying Reactions
1156(41)
24.1 The General Mechanism of Electrophilic Aromatic Substitution
1157(3)
24.2 Halogenation
1160(3)
24.3 Friedel-Crafts Aikylation
1163(3)
24.4 Limitations of Friedel--Crafts Aikylation
1166(4)
24.5 Friedel--Crafts Acylation
1170(3)
24.6 Nitration
1173(1)
24.7 Sulfonation
1174(2)
24.8 Organic Synthesis: Considerations of Carbocation Rearrangements and the Synthesis of Primary Alkylbenzenes
1176(1)
24.9 Organic Synthesis: Common Reactions Used Along with Electrophilic Aromatic Substitution Reactions
1177(20)
Chapter Summary and Key Terms
1186(1)
Reaction Tables
1187(3)
Problems
1190(7)
25 Aromatic Substitution 2 Reactions of Substituted Benzenes and Other Rings
1197(55)
25.1 Regiochemistry of Electrophilic Aromatic Substitution: Defining Ortho/Para and Meta Directors
1198(2)
25.2 What Characterizes Ortho/Para and Meta Directors, and Why?
1200(8)
25.3 Activation and Deactivation of Benzene toward Electrophilic Aromatic Substitution
1208(4)
25.4 Impact of Substituent Effects on the Outcome of Electrophilic Aromatic Substitution Reactions
1212(2)
25.5 Impact of Reaction Conditions on Substituent Effects
1214(2)
25.6 Electrophilic Aromatic Substitution on Disubstituted Benzenes
1216(6)
25.7 Electrophilic Aromatic Substitution Involving Aromatic Rings other than Benzene
1222(3)
25.8 Azo Coupling and Azo Dyes
1225(1)
25.9 Nucleophilic Aromatic Substitution Mechanisms
1226(6)
25.10 Organic Synthesis: Considerations of Regiochemistry, and Attaching Groups in the Correct Order
1232(1)
25.11 Organic Synthesis: Interconverting Ortho/Para and Meta Directors
1233(4)
25.12 Organic Synthesis: Considerations of Protecting Groups
1237(15)
Chapter Summary and Key Terms
1240(1)
Reaction Table
1241(1)
Problems
1242(10)
26 The Diels--Alder Reaction, Syn Dihydroxylation, and Oxidative Cleavage
1252(52)
26.1 Curved Arrow Notation and Examples of Diels--Alder Reactions
1253(4)
26.2 Conformation of the Diene in Diels--Alder Reactions
1257(3)
26.3 Substituent Effects on the Reaction Rate of Diels--Alder Reactions
1260(2)
26.4 Stereochemistry of Diels--Alder Reactions
1262(6)
26.5 Regiochemistry of Diels--Alder Reactions
1268(3)
26.6 A Deeper Look: The Reversibility of Diels--Alder Reactions; the Retro Diels--Alder Reaction
1271(2)
26.7 A Deeper Look: A Molecular Orbital Picture of the Diels--Alder Reaction
1273(6)
26.8 Syn Dihydroxylation of Alkenes and Alkynes with OsO4 or KMnO4
1279(2)
26.9 Oxidative Cleavage of Alkenes and Alkynes
1281(6)
26.10 Organic Synthesis: The Diels--Alder Reaction in Synthesis
1287(17)
Chapter Summary and Key Terms
1290(1)
Reaction Tables
1291(2)
Problems
1293(11)
27 Reactions Involving Radicals
1304(50)
27.1 Homolysis: Curved Arrow Notation and Radical Initiators
1305(3)
27.2 Structure and Stability of Alkyl Radicals
1308(6)
27.3 Common Elementary Steps That Radicals Undergo
1314(3)
27.4 Radical Halogenation of Alkanes: Synthesis of Alkyl Halides
1317(15)
27.5 Radical Addition of HBr: Anti-Markovnikov Addition
1332(3)
27.6 Stereochemistry of Radical Halogenation and HBr Addition
1335(2)
27.7 Dissolving Metal Reductions: Hydrogenation of Alkenes and Alkynes
1337(4)
27.8 Organic Synthesis: Radical Reactions in Synthesis
1341(13)
Chapter Summary and Key Terms
1344(1)
Reaction Table
1345(1)
Problems
1346(8)
28 Polymers
1354(1)
28.1 Radical Polymerization: Polystyrene as a Model
1355(13)
28.2 Anionic and Cationic Polymerization Reactions
1368(3)
28.3 Ziegler--Natta Catalysts and Coordination Polymerization
1371(1)
28.4 Ring-Opening Polymerization Reactions
1372(2)
28.5 Step-Growth Polymerization
1374(6)
28.6 Linear, Branched, and Network Polymers
1380(2)
28.7 Modification of Pendant Groups
1382(3)
28.8 Cross-linking
1385(2)
28.9 General Aspects of Polymer Structure
1387(5)
28.10 Properties of Polymers
1392(6)
28.11 Uses of Polymers: The Relationship between Structure and Function in Materials for Food Storage
1398(2)
28.12 Going Green with Polymers: Recycling, Biodegradable Polymers, and Renewable Sources
1400(3)
The Organic Chemistry of Biomolecules
28.13 Biological Polymers
1403(9)
Chapter Summary and Key Terms
1412(1)
Problems
1413
29 Biomolecules 1 An Overview of the Four Major Classes of Biomolecules
PART 1 PROTEINS AND AMINO ACIDS
29.1 Amino Acids as Building Blocks of Proteins
29.2 Acid-Base Properties of Amino Acids: Ionization State as a Function of pH
29.3 Electrophoresis and Isoelectric Focusing of Amino Acids
29.4 Levels of Protein Structure: Primary, Secondary, Tertiary, and Quaternary Structures
29.5 Sequencing Peptides
29.6 Synthesizing Peptides in the Laboratory
PART 2 CARBOHYDRATES AND MONOSACCHARIDES
29.7 Monosaccharides as Building Blocks of Carbohydrates
29.8 Classification of Monosaccharides, and the D Family of Aldohexoses
29.9 The Fischer Proof of the Structure of Glucose
29.10 Ring Closing and Ring Opening of Sugars
29.11 Glycosides, Glycosidic Linkages, and Reducing Sugars
29.12 Polysaccharide Structure and Function
PART 3 NUCLEIC ACIDS AND NUCLEOTIDES
29.13 Nucleotides as Building Blocks of Nucleic Acids
29.14 Complementarity among Nitrogenous Bases, and the DNA Double Helix
PART 4 UPIDS
29.15 Fats, Oils, and Fatty Acids
29.16 Phospholipids and Cell Membranes
29.17 Steroids, Terpenes, and Terpenoids
29.18 Prostaglandins
29.19 Waxes
Chapter Summary and Key Terms
Problems
30 Biomolecules 2 Representative Biochemical Processes Involving Biomolecules
30.1 Proteins as Enzymes
30.2 Metabolism of Carbohydrates: Glycolysis and Gluconeogenesis
30.3 Degradation and Synthesis of Fats, Oils, and Fatty Acids
30.4 Biosynthesis of Cholesterol and Terpenes
30.5 Storing and Accessing Genetic Information in DNA
30.6 Cell Signaling: An Example Involving G Proteins
Chapter Summary and Key Terms
Problems
Appendix A Values of pKa for Various Acids 1(3)
Appendix B Characteristic Reactivities of Particular Compound Classes 4(5)
Appendix C Reactions That Alter the Carbon Skeleton 9(6)
Appendix D Synthesizing Particular Compound Classes via Functional Group Transformations 15(18)
Appendix E Trivial Names or Common Names 33
Glossary 1(1)
Answers to Your Turns 1(1)
Credits 1(1)
Index 1
Joel Karty earned his BS in chemistry at the University of Puget Sound and his PhD at Stanford University. He carried out postdoctoral work with Stephen Craig at Duke University and began teaching at Elon University in the fall of 2001, where he currently holds the rank of full professor. At Elon, Joel teaches primarily the organic chemistry sequence and general chemistry, as well as physical chemistry. In the summers, he teaches an organic chemistry preparatory course as part of the SMDEP program at the Summer Biomedical Sciences Institute sponsored by the Duke University School of Medicine. His research interests include studying the contributions by resonance and inductive effects in fundamental chemical systems, and he also investigates the mechanism for pattern formation in periodic precipitation reactions (such as the Liesegang phenomenon). Joel is the author of the very successful student supplement, The Nuts and Bolts of Organic Chemistry (2005), which has gone into its second edition as Get Ready for Organic Chemistry (2011).
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