Organic Reactions and Their Mechanisms By PS Kalsi Third Edition (informative)
Free download Organic Reactions and their Mechanisms By PS Kalsi Third Edition
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PS Kalsi
Table of Contents in Organic Reactions and their Mechanisms By PS Kalsi Third Edition
hapter 1 Fundamental Principles and Special Topics
1.1 Structure and Bonding in Organic Compounds
1.2 Electronegativity—Dipole Moment
1.3 Inductive and Field Effects
1.4 Hydrogen Bond
1.5 Other Weaker Bonds
1.6 Bond Dissociation Energy
1.7 The Hammett Equation—Linear Free Energy Relationship
1.8 Taft Equation
1.9 Steric Effects, Strain and Bredt Rule
Problems
Answers to the Problems
Chapter 2 Delocalized Chemical Bonding
2.1 1, 3-butadiene a Typical Conjugated System
2.2 Resonance
2.3 Aromaticity
2.4 The Terms Aromatic, Antiaromatic and Nonaromatic
2.5 Annulenes
2.6 The Frost Circle—Molecular Orbital Description of Aromaticity and
Antiaromaticity
2.7 Aromatic and Antiaromatic Ions
2.8 Other Non-Benzenoid Aromatic Compounds
2.9 Heterocyclic Aromatic Compounds
2.10 Metallocenes and Related Compounds
2.11 Fused Benzenoids and Fullerenes
2.12 Homoaromatic Compounds
2.13 Hyperconjugation
2.14 Hexahelicene
2.15 Tautomerism
Problems
Answers to the Problems
Chapter 3 Organic Acids and Bases
3.1 The Bronsted-Lowry Concepts of Acids and Bases
3.2 The Lewis Definition of Acids and Bases
3.3 The Relation Between Structure and Acidity
3.4 Bases
3.5 Relation Between Structure and Basicity
3.6 Synthetic Applications of Lithium Diisopropylamide (LDA)
3.7 Acid-Base Reactions
3.8 The Effects of the Solvent on Acid and Base Strength
3.9 Leveling Effect
3.10 Hard and Soft Acids and Bases
Problems
Answers to the Problems
Chapter 4 Organic Reactions and the Determination of
their Mechanisms
4.1 Mechanistic Classification
4.2 Nucleophiles and Electrophiles
4.3 Electron Movement
4.4 Equilibria and Free Energy
4.5 Free Energy Change in Relation to Bond Strengths and
Degree of Order in a System
4.6 Reaction Rates
4.7 The Transition State—Activation Energy
4.8 Transition State Theory—Measurement of Activation Energy
4.9 Reaction Profile Diagrams 137
4.10 The Rate Determining Step 138
4.11 Thermodynamic and Kinetic Control 139
4.12 Applications of Kinetic Principles 141
4.13 The Curtin-Hammett Principle—Importance of Transition State 144
4.14 Microscopic Reversibility 145
4.15 Methods of Determining Mechanisms 146
4.16 Reactive Intermediates 154
Problems 174
Answers to the Problems 175
Chapter 5 Aliphatic Nucleophilic Substitution and 176–215
its Synthetic Applications
5.1 Introduction 176
5.2 Synchronous Substitution—SN2 Process 182
5.3 Substitution by Ionization—SN1 Mechanism 196
5.4 SN1 Versus SN2 Reactions 198
5.5 Other Aliphatic Substitution Pathways 200
5.6 The Role of Ion Pairs 202
5.7 Neighbouring Group Participation and Nonclassical Carbocations 204
5.8 Nucleophilic Substitution at Silicon 212
Problems 212
Answers to the Problems 214
Chapter 6 Common Organic Reactions and their 216–262
Mechanisms
6.1 Base Catalysed Reactions (Formation of Carbon-Carbon Bonds) 216
6.2 Stork Enamine Reactions (Formation of Carbon-Carbon Bonds)— 239
Reaction of an Enamine with Reactive Electrophiles
6.3 Acid Catalysed Reactions (Formation of Carbon-Carbon Bonds) 246
6.4 Reactions of Carboxylic Acids and their Derivatives 250
6.5 Hydrolysis of Amides 257
Problems 258
Answers to the Problems 260
Chapter 7 Reagents in Organic Synthesis and Relevant 263–328
Name Reactions
7.1 Organotransition Metal Reagents 263
7.2 Some Transition Metal Organometallic Reactions 266
7.3 Phosphorus Containing Reagents 280
7.4 Organosulphur Compounds: Sulphur Ylides 289
7.5 Silicon Reagents 297
7.6 Boron Containing Reagents 304
7.7 Organometallic Reagents 316
Problems 326
Answers to the Problems 327
Chapter 8 Electrophilic Aromatic Substitution 329–365
8.1 General View—The Arenium Ion—The Arenium Ion
Mechanism—SE2 Reaction 329
8.2 Electrophilic Substitution on Monosubstituted Benzenes—Orientation 340
and Reactivity
8.3 Electrophilic Substitution in Naphthalene and Larger Polycyclic 352
Aromatic Hydrocarbons
8.4 Attack of the Electrophile at a Carbon already Bearing a Substituent 353
(Ipso Position)—Ipso Substitution
8.5 Aromatic Rearrangements 355
8.6 Some Name Reactions 357
8.7 Electrophilic Substitution on Heteroaromatic Compounds 358
8.8 Diazonium Coupling 361
Problems 362
Answers to the Problems 363
Chapter 9 Aromatic Nucleophilic Substitution 366–379
9.1 The SNAr Mechanism—The Addition—Elimination Mechanism— 366
The General Nucleophilic Aromatic Ipso Substitution
9.2 The SN1 Mechanism in Nucleophilic Aromatic Substitution— 369
The Aryl Cation Mechanism—Diazonium Salts
9.3 Nucleophilic Aromatic Substitution by Elimination—Addition— 370
The Benzyne Mechanism
9.4 Benzyne—A Strained Cycloalkyne 373
9.5 Nucleophilic Substitution of Pyridine—The Chichibabin Reaction 376
9.6 Nucleophilic Substitution to Arenechromium Carbonyl Complexes 376
Problems 378
Answers to the Problems 378
Chapter 10 Photochemistry
Chapter 11 Addition to Carbon-Carbon and Carbon-Hetero
Multiple Bonds
Chapter 12 Elimination Reactions
Chapter 13 Oxidation Methods
Chapter 14 Reduction Methods
Chapter 15 Molecular Rearrangements
15.1 Rearrangements to Electron Deficient Carbon
15.2 Rearrangements to Electron Deficient Nitrogen
15.3 Rearrangements to Electron Deficient Oxygen
15.4 Rearrangement to Electron Rich Carbon
15.5 Aromatic Rearrangements
15.6 Free Radical Rearrangements
Problems
Answers to the Problems
Chapter 16 Free Radical Reactions
16.1 Structure, Stability and Geometry
16.2 Preparation
16.3 Properties of Free Radicals
16.4 Aromatic Nucleophilic Substitution—SRN1 Substitution
16.5 Homolytic Aromatic Substitution
16.6 Some Name Reactions
16.7 The Coupling of Alkynes
16.8 Reactions Involving Electron Transfer Steps
16.9 Molecular Rearrangements
16.10 Some Further Substitution and Other Reactions
Problems
Answers to the Problems
Chapter 17 Pericyclic Reactions
17.1 Conservation of Molecular Orbital Symmetry
17.2 Methods to Explain Pericyclic Reactions
17.3 Electrocyclic Reactions (FMO-Approach)
17.4 Cycloadditions (FMO-Approach)
17.5 1, 3-Dipolar Cycloadditions
17.6 Cheletropic Reactions
17.7 Sigmatropic Rearrangements
17.8 The ENE Reaction
17.9 Aromatic Transition States
17.10 Möbius-Hückel Analysis (PMO) Approach
17.11 Correlation Diagram Method
Problems
Answers to the Problems
References and Further Reading
Index
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