Ch07 Image

Chapter 7 builds upon the foundations of curved arrow notation and charge stability that students learn in Chapter 6. Students see that ionic reactions are driven largely by the flow of electrons from an electron-rich site to an electron-poor and that total bond energy is also an important driving force. Students also learn how to simplify ionic and organometallic species to work more comfortably with mechanisms. These concepts are applied toward the ten most common elementary steps that make up the bulk of multistep mechanisms students will encounter throughout the year. In the new Second Edition Karty aims at expanding students’ understanding of organic chemistry through introducing biomolecules, special interest boxes, green chemistry, and “connections” boxes, where he helps students to make a connection between chemistry and the products they use in their everyday lives.

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Brief Contents

Chapter 1 Atomic and Molecular Structure 1

Interchapter A Nomenclature: The Basic System for Naming Simple Organic Compounds: Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes, and Ethers

Chapter 2 Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties

Chapter 3 Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals

Interchapter B Naming Alkenes, Alkynes, and Benzene Derivatives

Chapter 4 Isomerism 1: Conformational and Constitutional Isomers

Chapter 5 Isomerism 2: Chirality, Enantiomers, and Diastereomers

Interchapter C Stereochemistry in Nomenclature: R and S Configurations about Asymmetric Carbons and Z and E Configurations about Double Bonds

Chapter 6 The Proton Transfer Reaction: An Introduction to Mechanisms, Thermodynamics, and Charge Stability

Chapter 7 An Overview of the Most Common Elementary Steps

Interchapter D Molecular Orbital Theory, Hyperconjugation, and Chemical Reactions

Interchapter E Naming Compounds with a Functional Group That Calls for a Suffix 1: Alcohols, Amines, Ketones, and Aldehydes

Chapter 8 An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and Their Comparisons to SN2 and E2 Reactions

Interchapter F Naming Compounds with a Functional Group That Calls for a Suffix 2: Carboxylic Acids and Their Derivatives

Chapter 9 Nucleophilic Substitution and Elimination Reactions 1: Competition among SN2, SN1, E2, and E1 Reactions

Chapter 10 Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis

Chapter 11 Electrophilic Addition to Nonpolar π Bonds 1: Addition of a Brønsted Acid

Chapter 12 Electrophilic Addition to Nonpolar π Bonds 2: Reactions Involving Cyclic Transition States

Chapter 13 Organic Synthesis 1: Beginning Concepts in Designing Multistep Syntheses

Chapter 14 Orbital Interactions 2: Extended π Systems, Conjugation, and Aromaticity

Chapter 15 Structure Determination 1: Ultraviolet–Visible and Infrared Spectroscopies

Chapter 16 Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry

Chapter 17 Nucleophilic Addition to Polar π Bonds 1: Addition of Strong Nucleophiles

Chapter 18 Nucleophilic Addition to Polar π Bonds 2: Weak Nucleophiles and Acid and Base Catalysis

Chapter 19 Organic Synthesis 2: Intermediate Topics in Synthesis Design, and Useful Redox and Carbon–Carbon Bond-Forming Reactions

Chapter 20 Nucleophilic Addition–Elimination Reactions 1: The General Mechanism Involving Strong Nucleophiles

Chapter 21 Nucleophilic Addition–Elimination Reactions 2: Weak Nucleophiles

Chapter 22 Aromatic Substitution 1: Electrophilic Aromatic Substitution on Benzene; Useful Accompanying Reactions

Chapter 23 Aromatic Substitution 2: Reactions of Substituted Benzene and Other Rings 1104

Chapter 24 The Diels–Alder Reaction and Other Pericyclic Reactions

Chapter 25 Reactions Involving Free Radicals

Interchapter G Fragmentation Pathways in Mass Spectrometry

Chapter 26 Polymers

Table of Contents

 

1 Atomic and Molecular Structure 1

1.1 What Is Organic Chemistry?
1.2 Why Carbon?
1.3 Atomic Structure and Ground State Electron Configurations
1.4 The Covalent Bond: Bond Energy and Bond Length
1.5 Lewis Dot Structures and the Octet Rule
1.6 Strategies for Success: Drawing Lewis Dot Structures Quickly
1.7 Electronegativity, Polar Covalent Bonds, and Bond Dipoles
1.8 Ionic Bonds
1.9 Assigning Electrons to Atoms in Molecules: Formal Charge
1.10 Resonance Theory
1.11 Strategies for Success: Drawing All Resonance Structures
1.12 Shorthand Notations
1.13 An Overview of Organic Compounds: Functional Groups
The Organic Chemistry of Biomolecules
1.14 An Introduction to Proteins, Carbohydrates, and Nucleic Acids: Fundamental Building Blocks and Functional Groups

INTERCHAPTER A Nomenclature: The Basic System for Naming Simple Organic Compounds: Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes, and Ethers

A.1 The Need for Systematic Nomenclature: An Introduction to the IUPAC System
A.2 Alkanes and Substituted Alkanes
A.3 Haloalkanes and Nitroalkanes: Roots, Prefixes, and Number Locators
A.4 Alkyl Substituents: Branched Alkanes and Substituted Branched Alkanes
A.5 Cyclic Alkanes and Cyclic Alkyl Groups
A.6 Ethers and Alkoxy Groups
A.7 Trivial Names or Common Names

2 Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties

2.1 Valence Shell Electron Pair Repulsion (VSEPR) Theory: Three-Dimensional       Geometry
2.2 Dash–Wedge Notation
2.3 Strategies for Success: The Molecular Modeling Kit
2.4 Net Molecular Dipoles and Dipole Moments
2.5 Physical Properties, Functional Groups, and Intermolecular Interactions
2.6 Melting Points, Boiling Points, and Intermolecular Interactions
2.7 Solubility
2.8 Strategies for Success: Ranking Boiling Points and Solubilities of Structurally Similar Compounds
2.9 Protic and Aprotic Solvents
2.10 Soaps and Detergents
The Organic Chemistry of Biomolecules
2.11 An Introduction to Lipids

3 Orbital Interactions 1
Hybridization and Two-Center Molecular Orbitals

3.1 Atomic Orbitals and the Wave Nature of Electrons
3.2 Interaction between Orbitals: Constructive and Destructive Interference
3.3 An Introduction to Molecular Orbital Theory and σ Bonds: An Example with H2
3.4 Hybrid Atomic Orbitals and Geometry
3.5 Valence Bond Theory and Other Orbitals of σ Symmetry: An Example with Ethane (H3C[[sb]]CH3)
3.6 An Introduction to π Bonds: An Example with Ethene (H2C[[db]]CH2)
3.7 Nonbonding Orbitals: An Example with Formaldehyde (H2C[[db]]O)
3.8 Triple Bonds: An Example with Ethyne (HC[[tb]]CH)
3.9 Bond Rotation about Single and Double Bonds: Cis and Trans Configurations
3.10 Strategies for Success: Molecular Models and Extended Geometry about Single and Double Bonds
3.11 Hybridization, Bond Characteristics, and Effective Electronegativity

INTERCHAPTER B Naming Alkenes, Alkynes, and Benzene Derivatives
B.1 Alkenes, Alkynes, Cycloalkenes, and Cycloalkynes: Molecules with One C[[db]]C or C[[tb]]C
 

B.2 Molecules with Multiple C[[db]]C or C[[tb]]C Bonds
B.3 Benzene and Benzene Derivatives
B.4 Trivial Names Involving Alkenes, Alkynes, and Benzene Derivatives

4 Isomerism 1
Conformational and Constitutional Isomers

4.1 Isomerism: A Relationship
4.2 Conformers: Rotational Conformations, Newman Projections, and Dihedral Angles
4.3 Conformers: Energy Changes and Conformational Analysis
4.4 Conformers: Cyclic Alkanes and Ring Strain
4.5 Conformers: The Most Stable Conformations of Cyclohexane, Cyclopentane, Cyclobutane, and Cyclopropane
4.6 Conformers: Cyclopentane, Cyclohexane, Pseudorotation, and Chair Flips
4.7 Strategies for Success: Drawing Chair Conformations of Cyclohexane
4.8 Conformers: Monosubstituted Cyclohexanes
4.9 Conformers: Disubstituted Cyclohexanes, Cis and Trans Isomers, and Haworth Projections
4.10 Strategies for Success: Molecular Modeling Kits and Chair Flips
4.11 Constitutional Isomerism: Identifying Constitutional Isomers
4.12 Constitutional Isomers: Index of Hydrogen Deficiency (Degree of Unsaturation)
4.13 Strategies for Success: Drawing All Constitutional Isomers of a Given Formula
The Organic Chemistry of Biomolecules
4.14 Constitutional Isomers and Biomolecules: Amino Acids and Monosaccharides
4.15 Saturation and Unsaturation in Fats and Oils

5 Isomerism 2
Chirality, Enantiomers, and Diastereomers

5.1 Defining Configurational Isomers, Enantiomers, and Diastereomers
5.2 Enantiomers, Mirror Images, and Superimposability
5.3 Strategies for Success: Drawing Mirror Images
5.4 Chirality
5.5 Diastereomers
5.6 Fischer Projections and Stereochemistry
5.7 Strategies for Success: Converting between Fischer Projections and Zigzag Conformations
5.8 Physical and Chemical Properties of Isomers
5.9 Stability of Double Bonds and Chemical Properties of Isomers
5.10 Separating Configurational Isomers
5.11 Optical Activity
The Organic Chemistry of Biomolecules
5.12 The Chirality of Biomolecules
5.13 The D/L System for Classifying Monosaccharides and Amino Acids
5.14 The D Family of Aldoses

INTERCHAPTER C Stereochemistry in Nomenclature:
R and S Configurations about Asymmetric Carbons and Z and E Configurations about Double Bonds
 

C.1 Priority of Substituents and Stereochemical Configurations at Asymmetric Carbons: R/S Designations
C.2 Stereochemical Configurations of Alkenes: Z/E Designations

 6 The Proton Transfer Reaction
An Introduction to Mechanisms, Thermodynamics, and Charge Stability

6.1 An Introduction to Reaction Mechanisms: The Proton Transfer Reaction and Curved Arrow Notation
6.2 Chemical Equilibrium and the Equilibrium Constant, Keq
6.3 Thermodynamics and Gibbs Free Energy
6.4 Strategies for Success: Functional Groups and Acidity
6.5 Relative Strengths of Charged and Uncharged Acids: The Reactivity of Charged Species
6.6 Relative Acidities of Protons on Atoms with Like Charges
6.7 Strategies for Success: Ranking Acid and Base Strengths—The Relative Importance of Effects on Charge
6.8 Strategies for Success: Determining Relative Contributions by Resonance Structures
The Organic Chemistry of Biomolecules
6.9 The Structure of Amino Acids in Solution as a Function of pH
6.10 Electrophoresis and Isoelectric Focusing

7 An Overview of the Most Common Elementary Steps

7.1 Mechanisms as Predictive Tools: The Proton Transfer Step Revisited
7.2 Bimolecular Nucleophilic Substitution (SN2) Steps
7.3 Bond-Formation (Coordination) and Bond-Breaking (Heterolysis) Steps
7.4 Nucleophilic Addition and Nucleophile Elimination Steps
7.5 Bimolecular Elimination (E2) Steps
7.6 Electrophilic Addition and Electrophile Elimination Steps
7.7 Carbocation Rearrangements: 1,2-Hydride Shifts and 1,2-Alkyl Shifts
7.8 The Driving Force for Chemical Reactions
7.9 Keto–Enol Tautomerization: An Example of Bond Energies as the Major Driving Force

INTERCHAPTER D Molecular Orbital Theory, Hyperconjugation, and Chemical Reactions

D.1 Relative Stabilities of Carbocations and Alkenes: Hyperconjugation and Negative Hyperconjugation
D.2 MO Theory and Chemical Reactions

INTERCHAPTER E Naming Compounds with a Functional Group That Calls for a Suffix 1:
Alcohols, Amines, Ketones, and Aldehydes

E.1 The Basic System for Naming Compounds Having a Functional Group That Calls for a Suffix: Alcohols and Amines
E.2 Naming Ketones and Aldehydes
E.3 Trivial Names of Alcohols, Amines, Ketones, and Aldehydes

8  An Introduction to Multistep Mechanisms
SN1 and E1 Reactions and Their Comparisons to SN2 and E2 Reactions

8.1 The Unimolecular Nucleophilic Substitution (SN1) Reaction
8.2 The Unimolecular Elimination (E1) Reaction
8.3 Direct Experimental Evidence for Reaction Mechanisms
8.4 The Kinetics of SN2, SN1, E2, and E1 Reactions
8.5 Stereochemistry of Nucleophilic Substitution and Elimination Reactions
8.6 The Reasonableness of a Mechanism: Proton Transfers and Carbocation Rearrangements
8.7 Resonance-Delocalized Intermediates in Mechanisms

9 Nucleophilic Substitution and Elimination Reactions 1:
Competition among SN2, SN1, E2, and E1 Reactions

9.1 The Competition among SN2, SN1, E2, and E1 Reactions
9.2 Rate-Determining Steps Revisited: Simplified Pictures of the SN2, SN1, E2, and E1 Reactions
9.3 Factor 1: Strength of the Attacking Species
9.4 Factor 2: Concentration of the Attacking Species
9.5 Factor 3: Leaving Group Ability
9.6 Factor 4: Type of Carbon Bonded to the Leaving Group
9.7 Factor 5: Solvent Effects
9.8 Factor 6: Heat
9.9 Predicting the Outcome of an SN1/SN2/E1/E2 Competition
9.10 Regioselectivity in Elimination Reactions: Zaitsev’s Rule
9.11 Intermolecular Reactions versus Intramolecular Cyclizations
9.12 Kinetic Control, Thermodynamic Control, and Reversibility
The Organic Chemistry of Biomolecules
9.13 Nucleophilic Substitution Reactions and Monosaccharides: The Formation and Hydrolysis of Glycosides

INTERCHAPTER F Naming Compounds with a Functional Group That Calls for a Suffix 2:
Carboxylic Acids and Their Derivatives

F.1 Naming Carboxylic Acids, Acid Chlorides, Amides, and Nitriles
F.2 Naming Esters and Acid Anhydrides
F.3 Trivial Names of Carboxylic Acids and Their Derivatives

10 Nucleophilic Substitution and Elimination Reactions 2:
Reactions That Are Useful for Synthesis

10.1 Nucleophilic Substitution: Converting Alcohols into Alkyl Halides Using PBr3 and PCl3
10.2 Nucleophilic Substitution: Alkylation of Ammonia and Amines
10.3 Nucleophilic Substitution: Alkylation of α Carbons
10.4 Nucleophilic Substitution: Halogenation of α Carbons
10.5 Nucleophilic Substitution: Diazomethane Formation of Methyl Esters
10.6 Nucleophilic Substitution: Formation of Ethers and Epoxides
10.7 Nucleophilic Substitution: Epoxides and Oxetanes as Substrates
10.8 Elimination: Generating Alkynes via Elimination Reactions
10.9 Elimination: Hofmann Elimination

11  Electrophilic Addition to Nonpolar π Bonds 1:
Addition of a Brønsted Acid

11.1 The General Electrophilic Addition Mechanism: Addition of a Strong Brønsted Acid to an Alkene
11.2 Benzene Rings Do Not Readily Undergo Electrophilic Addition of Brønsted Acids
11.3 Regiochemistry: Production of the More Stable Carbocation and Markovnikov’s Rule
11.4 Carbocation Rearrangements
11.5 Stereochemistry
11.6 Addition of a Weak Acid: Acid Catalysis
11.7 Electrophilic Addition of a Strong Brønsted Acid to an Alkyne
11.8 Acid-Catalyzed Hydration of an Alkyne: Synthesis of a Ketone
11.9 Electrophilic Addition of a Brønsted Acid to a Conjugated Diene: 1,2-Addition and 1,4-Addition
11.10 Kinetic versus Thermodynamic Control in Electrophilic Addition to a Conjugated Diene
The Organic Chemistry of Biomolecules
11.11 Terpene Biosynthesis: Carbocation Chemistry in Nature

12  Electrophilic Addition to Nonpolar π Bonds 2:
Reactions Involving Cyclic Transition States

12.1 Electrophilic Addition via a Three-Membered Ring: The General Mechanism
12.2 Electrophilic Addition of Carbenes: Formation of Cyclopropane Rings
12.3 Electrophilic Addition Involving Molecular Halogens: Synthesis of 1,2-Dihalides and Halohydrins
12.4 Oxymercuration–Reduction: Addition of Water
12.5 Epoxide Formation Using Peroxyacids
12.6 Hydroboration–Oxidation: Anti-Markovnikov Syn Addition of Water to an Alkene
12.7 Hydroboration–Oxidation of Alkynes

13  Organic Synthesis 1:
Beginning Concepts in Designing Multistep Syntheses

13.1 Writing the Reactions of an Organic Synthesis
13.2 Cataloging Reactions: Functional Group Transformations and Carbon–Carbon Bond Formation/Breaking Reactions
13.3 Retrosynthetic Analysis: Thinking Backward to Go Forward
13.4 Synthetic Traps
13.5 Choice of the Solvent
13.6 Considerations of Stereochemistry in Synthesis
13.7 Strategies for Success: Improving Your Proficiency with Solving Multistep Syntheses
13.8 Choosing the Best Synthesis Scheme

14  Orbital Interactions 2:
Extended π Systems, Conjugation, and Aromaticity

14.1 The Shortcomings of VB Theory
14.2 Multiple-Center MOs
14.3 Aromaticity and Hückel’s Rules
14.4 The MO Picture of Benzene: Why It’s Aromatic
14.5 The MO Picture of Cyclobutadiene: Why It’s Antiaromatic
14.6 Aromaticity in Larger Rings: [n]Annulenes
14.7 Aromaticity and Multiple Rings
14.8 Heterocyclic Aromatic Compounds
14.9 Aromatic Ions
14.10 Strategies for Success: Counting π Systems and π Electrons Using the Lewis Structure
The Organic Chemistry of Biomolecules
14.11 Aromaticity and DNA

15  Structure Determination 1:
Ultraviolet–Visible and Infrared Spectroscopies

15.1 An Overview of Ultraviolet–Visible Spectroscopy
15.2 The UV–Vis Spectrum: Photon Absorption and Electron Transitions
15.3 Effects of Structure on λmax
15.4 IR Spectroscopy
15.5 A Closer Look at Some Important IR Absorption Bands
15.6 Structure Elucidation Using IR Spectroscopy

16  Structure Determination 2:
Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry

16.1 NMR Spectroscopy: An Overview
16.2 Nuclear Spin and the NMR Signal
16.3 Chemical Distinction and the Number of NMR Signals
16.4 Strategies for Success: The Chemical Distinction Test and Molecular Symmetry
16.5 The Time Scale of NMR Spectroscopy
16.6 Chemical Shift
16.7 Characteristic Chemical Shifts, Inductive Effects, and Magnetic Anisotropy
16.8 Trends in Chemical Shift
16.9 Integration of Signals
16.10 Splitting of the Signal by Spin–Spin Coupling: The N + 1 Rule
16.11 Coupling Constants and Signal Resolution
16.12 Complex Signal Splitting
16.13 13C NMR Spectroscopy
16.14 DEPT 13C NMR Spectroscopy
16.15 Structure Elucidation Using NMR Spectroscopy
16.16 Mass Spectrometry: An Overview
16.17 Features of a Mass Spectrum, the Nitrogen Rule, and Fragmentation
16.18 Isotope Effects: M + 1 and M + 2 Peaks
16.19 Determining a Molecular Formula of an Organic Compoumd from the Mass Spectrum

17  Nucleophilic Addition to Polar π Bonds 1:
Addition of Strong Nucleophiles

17.1 An Overview of the General Mechanism: Addition of Strong Nucleophiles
17.2 Substituent Effects: Relative Reactivity of Ketones and Aldehydes in Nucleophilic Addition
17.3 Reactions of LiAlH4 and NaBH4
17.4 Sodium Hydride: A Strong Base but a Poor Nucleophile
17.5 Reactions of Organometallic Compounds: Alkyllithium Reagents and Grignard Reagents
17.6 Limitations of Alkyllithium and Grignard Reagents
17.7 Wittig Reagents and the Wittig Reaction: Synthesis of Alkenes
17.8 Generating Wittig Reagents
17.9 Direct Addition versus Conjugate Addition
17.10 Lithium Dialkylcuprates and the Selectivity of Organometallic Reagents
17.11 Organic Synthesis: Grignard and Alkyllithium Reactions in Synthesis
17.12 Organic Synthesis: Considerations of Direct Addition versus Conjugate Addition
17.13 Organic Synthesis: Considerations of Regiochemistry in the Formation of Alkenes

18  Nucleophilic Addition to Polar π Bonds 2:
Weak Nucleophiles and Acid and Base Catalysis

18.1 Weak Nucleophiles as Reagents: Acid and Base Catalysis
18.2 Formation and Hydrolysis Reactions Involving Acetals, Imines, Enamines, and Nitriles
18.3 The Wolff–Kishner Reduction
18.4 Enolate Nucleophiles: Aldol and Aldol-Type Additions
18.5 Aldol Condensations
18.6 Aldol Reactions Involving Ketones
18.7 Crossed Aldol Reactions
18.8 Intramolecular Aldol Reactions
18.9 Aldol Additions Involving Nitriles and Nitroalkanes
18.10 The Robinson Annulation
18.11 Organic Synthesis: Aldol Reactions in Synthesis
18.12 Organic Synthesis: Synthesizing Amines via Reductive Amination
The Organic Chemistry of Biomolecules
18.13 Ring Opening and Closing of Monosaccharides; Mutarotation

19  Organic Synthesis 2:
Intermediate Topics in Synthesis Design, and Useful Redox and Carbon–Carbon Bond-Forming Reactions

19.1 Umpolung in Organic Synthesis: Forming Bonds between Carbon Atoms Initially Bearing Like Charge; Making Organometallic Reagents
19.2 Relative Positioning of Heteroatoms in Carbon–Carbon Bond-Forming Reactions
19.3 Reactions That Remove a Functional Group Entirely from a Molecule: Reductions of C[[db]]O to CH2
19.4 Avoiding Synthetic Traps: Selective Reagents and Protecting Groups
19.5 Catalytic Hydrogenation
19.6 Oxidations of Alcohols and Aldehydes
19.7 Useful Reactions That Form Carbon–Carbon Bonds: Coupling and Alkene Metathesis

20  Nucleophilic Addition–Elimination Reactions 1:
The General Mechanism Involving Strong Nucleophiles

20.1 An Introduction to Nucleophilic Addition–Elimination Reactions: Transesterification
20.2 Acyl Substitution Involving Other Carboxylic Acid Derivatives: The Thermodynamics of Acyl Substitution
20.3 Reaction of an Ester with Hydroxide (Saponification) and the Reverse Reaction
20.4 Carboxylic Acids from Amides; the Gabriel Synthesis of Primary Amines
20.5 Haloform Reactions
20.6 Hydride Reducing Agents: Sodium Borohydride (NaBH4) and Lithium Aluminum Hydride (LiAlH4)
20.7 Specialized Reducing Agents: Diisobutylaluminum Hydride (DIBAH) and Lithium Tri-tert-butoxyaluminum Hydride (LTBA)
20.8 Organometallic Reagents

21  Nucleophilic Addition–Elimination Reactions 2:
Weak Nucleophiles

21.1 The General Nucleophilic Addition–Elimination Mechanism Involving Weak Nucleophiles: Alcoholysis and Hydrolysis of Acid Chlorides
21.2 Relative Reactivities of Acid Derivatives: Rates of Hydrolysis
21.3 Aminolysis of Acid Derivatives
21.4 Synthesis of Acid Halides: Getting to the Top of the Stability Ladder
21.5 The Hell–Volhard–Zelinsky Reaction: Synthesizing α-Bromo Carboxylic Acids
21.6 Sulfonyl Chlorides: Synthesis of Mesylates, Tosylates, and Triflates
21.7 Base and Acid Catalysis in Nucleophilic Addition–Elimination Reactions
21.8 Baeyer–Villiger Oxidations
21.9 Claisen Condensations
21.10 Organic Synthesis: Decarboxylation, the Malonic Ester Synthesis, and the Acetoacetic Ester Synthesis
21.11 Organic Synthesis: Protecting Carboxylic Acids and Amines
The Organic Chemistry of Biomolecules
21.12 Determining a Protein’s Primary Structure via Amino Acid Sequencing: Edman Degradation
21.13 Synthesis of Peptides

22  Aromatic Substitution 1:
Electrophilic Aromatic Substitution on Benzene; Useful Accompanying Reactions

22.1 The General Mechanism of Electrophilic Aromatic Substitutions
22.2 Halogenation
22.3 Friedel–Crafts Alkylation
22.4 Limitations of Friedel–Crafts Alkylations
22.5 Friedel–Crafts Acylation
22.6 Nitration
22.7 Sulfonation
22.8 Organic Synthesis: Considerations of Carbocation Rearrangements and the Synthesis of Primary Alkylbenzenes
22.9 Organic Synthesis: Common Reactions Used in Conjunction with Electrophilic Aromatic Substitution Reactions

23  Aromatic Substitution 2:
Reactions of Substituted Benzene and Other Rings

23.1 Regiochemistry of Electrophilic Aromatic Substitution: Defining Ortho/Para and Meta Directors
23.2 What Characterizes Ortho/Para and Meta Directors and Why?
23.3 The Activation and Deactivation of Benzene toward Electrophilic Aromatic Substitution
23.4 The Impacts of Substituent Effects on the Outcomes of Electrophilic Aromatic Substitution Reactions
23.5 The Impact of Reaction Conditions on Substituent Effects
23.6 Electrophilic Aromatic Substitution on Disubstituted Benzenes
23.7 Electrophilic Aromatic Substitution Involving Aromatic Rings Other than Benzene
23.8 Azo Coupling and Azo Dyes
23.9 Nucleophilic Aromatic Substitution Mechanisms
23.10 Organic Synthesis: Considerations of Regiochemistry; Attaching Groups in the Correct Order
23.11 Organic Synthesis: Interconverting Ortho/Para and Meta Directors
23.12 Organic Synthesis: Considerations of Protecting Groups

24  The Diels–Alder Reaction and Other Pericyclic Reactions

24.1 Curved Arrow Notation and Examples
24.2 Conformation of the Diene
24.3 Substituent Effects on the Reaction Rate
24.4 Stereochemistry of Diels–Alder Reactions
24.5 Regiochemistry of Diels–Alder Reactions
24.6 The Reversibility of Diels–Alder Reactions; the Retro Diels–Alder Reaction
24.7 Syn Dihydroxylation of Alkenes and Alkynes Using OsO4 or KMnO4
24.8 Oxidative Cleavage of Alkenes and Alkynes
24.9 Organic Synthesis: The Diels–Alder Reaction in Synthesis
24.10 A Molecular Orbital Picture of the Diels–Alder Reaction

25  Reactions Involving Free Radicals

25.1 Homolysis: Curved Arrow Notation and Radical Initiators
25.2 Structure and Stability of Alkyl Radicals
25.3 Common Elementary Steps That Free Radicals Undergo
25.4 Radical Halogenation of Alkanes: Synthesis of Alkyl Halides
25.5 Radical Addition of HBr: Anti-Markovnikov Addition
25.6 Stereochemistry of Free-Radical Halogenation and HBr Addition
25.7 Dissolving Metal Reductions: Hydrogenation of Alkenes and Alkynes
25.8 Organic Synthesis: Radical Reactions in Synthesis

INTERCHAPTER G Fragmentation Pathways in Mass Spectrometry

G.1 Alkanes
G.2 Alkenes and Aromatic Compounds
G.3 Alkyl Halides, Amines, Ethers, and Alcohols
G.4 Carbonyl-Containing Compounds

26  Polymers

26.1 Free Radical Polymerization: Polystyrene as a Model
26.2 Anionic and Cationic Polymerization Reactions
26.3 Ring-Opening Polymerization Reactions
26.4 Step-Growth Polymerization
26.5 Linear, Branched, and Network Polymers
26.6 Chemical Reactions after Polymerization
26.7 General Aspects of Polymer Structure
26.8 Properties of Polymers
26.9 Uses of Polymers: The Relationship between Structure and Function in Materials for Food Storage
26.10 Degradation and Depolymerization
The Organic Chemistry of Biomolecules
26.11 Biological Macromolecules

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