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ORGANIC CHEMISTRY
A Modern Approach
Volume-I
ABOUT THE AUTHOR

Nimai Tewari is a retired associate Professor, Department of Chemistry,

Katwa College (affiliated to The University of Burdwan), West Bengal.
A PhD in Organic Chemistry from Calcutta University, he has taught
the subject for a period of more than three decades. He has published
various research papers in national and international journals.
Apart from Organic Chemistry—A Modern Approach, Dr Tewari has
authored three more books on Organic Chemistry for undergraduate
and postgraduate students. His research interest includes Organic
Synthesis and Heterocyclic Chemistry.
ORGANIC CHEMISTRY
A Modern Approach
Volume-I

Nimai Tewari
Associate Professor (Retired)
Department of Chemistry
Katwa College
(affiliated to The University of Burdwan)
West Bengal

McGraw Hill Education (India) Private Limited

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Organic Chemistry—A Modern Approach (Volume-I)

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 Dedicated to
my daughter Aindrila
and
my son-in-law Ritam Mukherjee
whose forbearance, constant
encouragement and inspiration
made this work possible
 CONTENTS

Preface xv

1. Structure, Bonding and Properties of Organic Molecules 1.1–1.313

1.1 Hybridization, Bond Lengths, Bond Strengths or Bond Dissociation
Enthalpies, Bond Angles and VSEPR Theory 1.2
1.1.1 Hybridization 1.2
1.1.2 Bond Length 1.9
1.1.3 Bond Dissociation Enthalpy or Bond Dissociation Energy 1.9
1.1.4 Bond Angle 1.10
1.1.5 VESPR Theory and Molecular Geometry 1.11
Solved Problems 1.13
Study Problems 1.21
1.2 Electronegativity and Bond Polarity 1.22
Solved Problems 1.33
Study Problems 1.42
1.3 Molecular Formula as a Clue to Structure: Double Bond Equivalent (DBE) or
Index of Hydrogen Deficiency (IHD) 1.44
Solved Problems 1.44
Study Problems 1.46
1.4 Acids and Bases 1.46
1.4.1 Brönsted-Lowry Theory of Acids and Bases 1.46
1.4.2 Lewis Acid-Base Theory 1.52
Solved Problems 1.53
Study Problems 1.57
1.5 Inductive and Electrometric Effects 1.60
1.5.1 Inductive Effect 1.60
1.5.2 Field Effect 1.67
1.5.3 Electromeric Effect 1.67
Solved Problems 1.67
Study Problems 1.73
viii Contents

1.6 Resonance and Resonance Effect or Mesomeric Effect 1.75

1.6.1 Resonance Energy 1.77
1.6.2 Rules for Writing Meaningful Resonance Structures 1.78
1.6.3 Relative Contribution of Resonance Structures towards Resonance
Hybrid 1.78
1.6.4 Resonance or Mesomeric Effect 1.80
1.6.5 Isovalent and Heterovalent Resonance 1.81
1.6.6 Effect of Resonance on the Properties of Molecules 1.81
Solved Problems 1.98
Study Problems 1.112
1.7 Hyperconjugation 1.117
1.7.1 Sacrificial and Isovalent Hyperconjugation 1.119
1.7.2 Effect of Hyperconjugation on the Physical and Chemical Properties of
Molecules and on the Stabilities of Intermediates 1.119
Solved Problems 1.122
Study Problems 1.124
1.8 Steric Effect 1.125
1.8.1 Properties of Molecules Influenced by Steric Effect 1.126
1.8.2 Proton Sponges 1.132
1.8.3 Face Strain or F-Strain 1.133
1.8.4 Steric Acceleration and Steric Retardation 1.134
1.8.5 Bredt’s Rule 1.135
Solved Problems 1.138
Study Problems 1.142
1.9 Intermolecular Forces 1.147
1.9.1 Dipole–Dipole Interactions 1.147
1.9.2 van der Waals Forces 1.149
1.9.3 Effect of Intermolecular Forces on Different Properties of
Compounds 1.150
Solved Problems 1.161
Study Problems 1.167
1.10 Reactive Intermediates 1.170
1.10.1 Nonclassical Carbocation 1.177
1.10.2 Carbonium Ion and Carbenium Ion or Carbocation 1.178
Solved Problems 1.193
Study Problems 1.212
1.11 Tautomerism 1.218
1.11.1 Mechanism of Keto-enol Tautomerism 1.221
1.11.2 Difference between Resonance and Tautomerism 1.222
1.11.3 Position of the Tautomeric Equilibrium 1.223
1.11.4 Ring-chain Tautomerism 1.228
1.11.5 Valence Tautomerism 1.228
Solved Problems 1.228
Study Problems 1.236
 Contents ix

1.12 Aromaticity 1.240

1.12.1 Criteria for Aromaticity 1.240
1.12.2 Antiaromatic Compounds 1.242
1.12.3 Nonaromatic Compounds 1.242
1.12.4 Classification of Compounds as Aromatic, Antiaromatic and Nonaromatic
by Comparing their Stabilities with that of the Corresponding Open Chain
Compounds 1.243
1.12.5 Modern Definition of Aromaticity 1.243
1.12.6 Molecular Orbital Energy Diagram of Some Ions and Molecules 1.244
1.12.7 Use of Inscribed Polygon Method to Determine the Relative Energies
of p Molecular Orbitals for Cyclic Planar and Completely Conjugated
Compounds and to Classify Them as Aromatic and Antiaromatic 1.245
1.12.8 Classification of Some Molecules and Ions as Aromatic, Antiaromatic and
Nonaromatic 1.247
1.12.9 Homoaromatic Compounds 1.251
1.12.10 Some Chemical and Physical Consequences of Aromaticity 1.251
Solved Problems 1.262
Study Problems 1.267
1.13 Thermodynamics, Energy Diagrams and Kinetics of Organic Reactions 1.276
1.13.1 Thermodynamics 1.276
1.13.2 Energy Diagram 1.278
1.13.3 Kinetics 1.281
1.13.4 Catalysis 1.283
1.13.5 Hammond Postulate 1.284
1.13.6 Kinetic Control versus Thermodynamic Control of a Chemical Reaction 1.286
Solved Problems 1.287
Study Problems 1.295
1.14 Methods of Determining Mechanisms of Reactions 1.298
1.14.1 Kinetic Isotope Effects 1.305
Solved Problems 1.307
Study Problems 1.312

2. Principles of Stereochemistry 2.1–2.230

Introduction 2.2
2.1 Projection Formulas of Stereoisomers 2.3
2.1.1 Flying-Wedge Projection Formula 2.3
2.1.2 Fischer Projection Formula 2.4
2.1.3 Sawhorse Projection Formula 2.10
2.1.4 Newman Projection Formula 2.11
2.1.5 Interconversion of Projection Formulas 2.12
Solved Problems 2.16
Study Problems 2.25
2.2 Symmetry Elements 2.29
2.2.1 Simple Axis of Symmetry or Rotational Axis of Symmetry (Cn) 2.29
2.2.2 Plane of Symmetry (s) 2.33
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x Contents

2.2.3 Centre of Symmetry (i) 2.36

2.2.4 Alternating Axis of Symmetry (Sn) 2.37
2.2.5 Symmetric, Asymmetric and Dissymmetric Molecules 2.38
Solved Problems 2.39
Study Problems 2.56
2.3 Isomerism: Constitutional Isomers and Stereoisomers 2.58
2.3.1 Constitutional Isomers 2.58
2.3.2 Stereoisomers 2.59
2.3.3 Enantiomers and Diastereoisomers 2.59
Solved Problems 2.64
Study Problems 2.79
2.4 Molecular Chirality 2.84
2.4.1 Chiral and Achiral Molecules 2.84
2.4.2 Source of Chirality 2.85
2.4.3 Stereocentre or Stereogenic Centre 2.88
2.4.4 Meso Compounds 2.89
Solved Problems 2.91
Study Problems 2.104
2.5 Configuration and Configurational Nomenclature 2.108
2.5.1 D, L-System of Configurational Designation 2.109
2.5.2 Specification of Configuration: The R, S-System 2.111
2.5.3 Erythro and Threo Nomenclature of Compounds with Two Adjacent Chiral
Centres 2.124
2.5.4 The E-Z System of Designating Alkene Diastereoisomers 2.125
2.5.5 R, S and E, Z Assignment in the Same Molecule (Geometric
Enantiomerism) 2.127
2.5.6 Syn-anti Nomenclature for Aldols 2.128
2.5.7 Number of Stereoisomers for Compounds with Chiral Centres 2.129
2.5.8 Chirotopic and Achirotopic Atom in a Molecule 2.131
2.5.9 Prostereoisomerism and Topicity 2.133
Solved Problems 2.141
Study Problems 2.175
2.6 Optical Activity of Chiral Compounds 2.182
2.6.1 Plane-polarized Light 2.182
2.6.2 Optical Activity 2.182
2.6.3 Polarimeter 2.183
2.6.4 Specific Rotation 2.184
2.6.5 The Necessary and Sufficient Condition (the ultimate criterion) for Optical
Activity 2.186
2.6.6 Racemic Modification 2.187
2.6.7 Enantiomeric Excess (EE) or Optical Purity (EE) 2.187
2.6.8 Racemization 2.188
2.6.9 Resolution of Racemic Modification 2.192
Solved Problems 2.199
Study Problems 2.208
 Contents xi

2.7 Conformation of Acyclic Organic Molecules 2.211

2.7.1 Conformations of Ethane (CH3—CH3) 2.213
2.7.2 Conformations of Propane (CH3CH2CH3) 2.214
2.7.3 Conformations of Butane (CH3CH2CH2CH3) 2.215
2.7.4 Conformations of Chloroethane (CH3CH2Cl) 2.218
2.7.5 Conformations of 1,2-dichloroethane (ClCH2CH2Cl) 2.218
2.7.6 Conformations of Some Typical Acyclic Molecules 2.219
2.7.7 Invertomerism 2.220
Solved Problems 2.221
Study Problems 2.227

3. Nucleophilic Substitution Reactions at Saturated Carbon Atom 3.1–3.180

Introduction 3.2
3.1 The SN2 reaction 3.3
3.1.1 Example of SN2 Reaction 3.3
3.1.2 Kinetics of SN2 Reaction 3.3
3.1.3 Mechanism of SN2 Reaction 3.3
3.1.4 Stereochemistry of SN2 Reaction 3.5
3.1.5 Evidence in Favour of SN2 Mechanism 3.6
3.1.6 Factors Influencing SN2 Reaction Rate or SN2 Reactivity 3.7
Solved Problems 3.35
Study Problems 3.74
3.2 The SN1 Reaction 3.86
3.2.1 Example of SN1 Reaction 3.86
3.2.2 Kinetics of SN1 Reaction 3.86
3.2.3 Mechanism of SN1 Reaction 3.86
3.2.4 Stereochemistry of SN1 Reaction 3.87
3.2.5 Evidence in Favour of SN1 Mechanism 3.90
3.2.6 Factors Influencing SN1 Reaction Rate or SN1 Reactivity 3.91
3.2.7 Carbocation Rearrangements in SN1 Reactions 3.105
3.2.8 Comparison of the SN2 and SN1 Reactions 3.108
3.2.9 Summary of Reactivity of Alkyl Halide in Necleophilic Substitution
Reactions 3.108
3.2.10 Factors Favouring SN1 and SN2 Reactions 3.108
3.2.11 SNi and SNi¢ Mechanisms 3.109
3.2.12 SN1¢ Mechanism 3.112
3.2.13 Isotope Effects and Salt Effects (Methods used to Distinguish between SN1
and SN2 Type Reactions) 3.113
Solved Problems 3.114
Study Problems 3.135
3.3 Neighbouring Group Participation (NGP) 3.146
3.3.1 Definition 3.146
3.3.2 Mechanism of NGP 3.146
3.3.3 Example of NGP 3.146
3.3.4 Anchimeric Assistance 3.147
xii Contents

3.3.5 Evidence for Participation by a Neighbouring Group 3.148

3.3.6 Various Cases of Neighbouring Group Participation 3.148
Solved Problems 3.163
Study Problems 3.175

4. Elimination Reactions 4.1–4.128

Introduction 4.2
4.1 The E2 Reaction 4.4
4.1.1 Example of E2 Reaction 4.4
4.1.2 Kinetics of E2 Reaction 4.4
4.1.3 Mechanism of E2 Reaction 4.4
4.1.4 Stereochemistry of E2 Reaction 4.5
4.1.5 Evidence in Favour of the E2 Mechanism 4.32
4.1.6 Factors Influencing E2 Reaction Rate or E2 Reactivity 4.33
4.1.7 Factors that Govern the Proportions of E2 and SN2 Reactions 4.34
4.1.8 Regioselectivity in b-elimination Reactions (Orientation of p Bond in the
Product Alkene) 4.37
4.1.9 Hofmann Exhaustive Methylation or Hofmann Degradation 4.43
4.1.10 Fragmentations 4.45
4.1.11 Summary of the E2 Reaction 4.47
Solved Problems 4.47
Study Problems 4.74
4.2 The E1 Reaction 4.86
4.2.1 Example of E1 Reaction 4.86
4.2.2 Kinetics of E1 Reaction 4.87
4.2.3 Mechanism of E1 Reaction 4.87
4.2.4 Stereochemistry of E1 Reaction 4.88
4.2.5 Evidence in Favour of the E1 Mechanism 4.90
4.2.6 Factors Influencing E1 Reaction Rate or E1 Reactivity 4.90
4.2.7 Regioselectivity of E1 Reactions 4.90
4.2.8 Rearrangement of the Carbocation Intermediate Involved in an E1
Reaction 4.93
4.2.9 Acid-Catalyzed Dehydration of Alcohols 4.95
4.2.10 Dehydration using POCl3 and Pyridine 4.99
4.2.11 Factors Influencing the Extent of E1 and E2 Reactions 4.100
4.2.12 Factors that Govern the Proportions of E1 and SN1 Reactions 4.101
Solved Problems 4.102
Study Problems 4.114
4.3 The E1CB Reaction 4.118
4.3.1 Example of E1cB Reaction 4.118
4.3.2 Kinetics of E1cB Reaction 4.118
4.3.3 Mechanism of E1cB Reaction 4.118
4.3.4 The Nature of the Substrate 4.119
 Contents xiii

4.3.5 To Distinguish between E1cB and E2 Mechanisms 4.119

Solved Problems 4.121
Study Problems 4.125
4.4 a- or 1,1-Elimination 4.126
4.4.1 Example of a- or 1,1-Elimination Reaction 4.126
4.4.2 Kinetics of a- or 1,1-Elimination Reaction 4.126
4.4.3 Mechanism of a- or 1,1-Elimination Reaction 4.126
4.4.4 Structure of the Substrate Involved in a-Elimination 4.127
Solved Problems 4.127
Study Problems 4.128

Index I.1–I.6
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