Wiley's Solomons, Fryhle & Snyder Organic Chemistry for JEE (Main & Advanced), 4ed, 2026
ISBN: 9789363866744
996 pages
Publication Year: 2025
For more information write to us at: acadmktg@wiley.com
Description
Master Organic Chemistry for IIT JEE & Other Engineering Entrance Exams
This specially adapted edition of the globally acclaimed Organic Chemistry by Solomons, Fryhle & Snyder is tailored for students preparing for engineering entrance exams . Designed with the Indian exam pattern in mind, the book bridges the gap between conceptual clarity and exam relevance.
Reorganized to address the specific challenges faced by engineering aspirants, this edition enhances understanding through simplified explanations, streamlined theory, and a focused approach. Perfect for students aiming to build a strong foundation in Organic Chemistry and succeed in highly competitive exams.
Preface to the Original Edition iii
Preface to the Adapted Version ix
About the Authors xi
About the Adapting Authors xiii
To the Student xv
Organic Chemistry Animations and
Quizzes xvii
A Chapter wise Comparative Analysis of
JEE Advanced (2014–2024) Questions with
Focus Topics xxi
1
The Basics: Bonding and
Molecular Structure 1
1.1 Development of the Science of Organic Chemistry 1
1.2 Atomic Structure 2
1.3 The Structural Theory of Organic Chemistry 3
1.4 Chemical Bonds: The Octet Rule 5
1.5 Resonance Theory 7
1.6 Hyperconjugation 18
1.7 The Structure of Methane and Ethane:
sp3 Hybridization 25
1.8 The Structure of Ethene (Ethylene): sp2
Hybridization 26
1.9 The Structure of Ethyne (Acetylene): sp
Hybridization 29
1.10 How to Interpret and Write Structural Formulas 32
2
Families of Carbon Compounds:
Functional Groups and
Intermolecular Forces 43
2.1 Hydrocarbons: Representative Alkanes, Alkenes,
Alkynes, and Aromatic Compounds 44
2.2 Polar and Nonpolar Molecules 47
2.3 Functional Groups 49
2.4 Alkyl Halides or Haloalkanes 51
2.5 Alcohols 51
2.6 Ethers 52
2.7 Amines 53
2.8 Aldehydes and Ketones 54
2.9 Carboxylic Acids, Esters, and Amides 55
2.10 Nitriles 57
2.11 Summary of Important Families of Organic
Compounds 58
2.12 Physical Properties and Molecular Structure 59
2.13 Summary of Attractive Electric Forces 66
3
An Introduction to Organic
Reactions and Their Mechanisms:
Acids and Bases 73
3.1 Reactions and Their Mechanisms 73
3.2 Acid–Base Reactions 75
3.3 Lewis Acids and Bases 77
3.4 Heterolysis of Bonds to Carbon: Carbocations
and Carbanions 79
3.5 HOW TO Use Curved Arrows in Illustrating
Reactions 80
3.6 The Strength of Brønsted–Lowry Acids and Bases:
Ka and pKa 85
3.7 HOW TO Predict the Outcome of Acid–Base
Reactions 88
3.8 Relationships between Structure and Acidity 90
3.9 Energy Changes 94
3.10 The Relationship between the Equilibrium Constant
and the Standard Free-Energy Change, DG° 95
3.11 The Acidity of Carboxylic Acids versus Alcohols 96
3.12 The Effect of the Solvent on Acidity 99
3.13 Organic Compounds as Bases 100
3.14 Acids and Bases in Nonaqueous Solutions 101
3.15 Acid–Base Reactions and the Synthesis of
Deuterium- and Tritium-Labeled Compounds 103
3.16 Reaction of NaHCO3 as a Base 104
3.17 Steric Inhibition of Resonance (SIR) Effect 105
3.18 Ortho and Para Effects 106
4
Stereochemistry: Chiral
Molecules 127
4.1 Chirality and Stereochemistry 127
4.2 Isomerism: Constitutional Isomers and
Stereoisomers 129
4.3 Enantiomers and Chiral Molecules 130
4.4 A Single Chirality Center Causes a Molecule
to Be Chiral 131
4.5 More about the Biological Importance of Chirality 133
4.6 HOW TO Test for Chirality: Planes of Symmetry 135
4.7 Naming Enantiomers: The R,S-System 142
4.8 Properties of Enantiomers: Optical Activity 146
4.9 The Origin of Optical Activity 150
4.10 The Synthesis of Chiral Molecules 152
4.11 Chiral Drugs 154
4.12 Molecules with More than One Chirality Center 155
4.13 Fischer Projection Formulas 159
4.14 Stereoisomerism of Cyclic Compounds 160
4.15 Relating Configurations through Reactions in which
no Bonds to the Chirality Center are Broken 163
4.16 Separation of Enantiomers: Resolution 166
4.17 Compounds with Chirality Centers Other than
Carbon 169
4.18 Chiral Molecules That Do Not Possess a Chirality
Center 169
4.19 Biphenyl 170
4.20 Racemization of Biphenyl Compounds 172
4.21 Tautomerism 173
4.22 Gero Entropy 176
5
Nomenclature and Conformations
of Alkanes and Cycloalkanes 191
5.1 Introduction to Alkanes and Cycloalkanes 191
5.2 Shapes of Alkanes 192
5.3 HOW TO Name Alkanes, Alkyl Halides,
and Alcohols: The IUPAC System 194
5.4 HOW TO Name Cycloalkanes 201
5.5 HOW TO Name Alkenes and Cycloalkenes 204
5.6 HOW TO Name Alkynes 206
5.7 Physical Properties of Alkanes and Cycloalkanes 207
5.8 Sigma Bonds and Bond Rotation 209
5.9 Conformational Analysis of Butane 211
5.10 The Relative Stabilities of Cycloalkanes: Ring Strain 218
5.11 Conformations of Cyclohexane: The Chair
and the Boat 220
5.12 Substituted Cyclohexanes: Axial and
Equatorial Hydrogen Groups 222
5.13 Disubstituted Cycloalkanes: Cis–Trans Isomerism 225
5.14 Bicyclic and Polycyclic Alkanes 230
5.15 Chemical Reactions of Alkanes 231
5.16 Synthesis of Alkanes and Cycloalkanes 231
5.17 HOW TO Gain Structural Information from Molecular
Formulas and the Index of Hydrogen Deficiency 234
5.18 Applications of Basic Principles 235
6
Ionic Reactions
Nucleophilic Substitution and Elimination
Reactions of Alkyl Halides 243
6.1 Alkyl Halides 243
6.2 Nucleophilic Substitution Reactions 245
6.3 Nucleophiles 246
6.4 Leaving Groups 248
6.5 Kinetics of a Nucleophilic Substitution
Reaction:
An SN2 Reaction 248
6.6 A Mechanism for the SN2 Reaction 249
6.7 Transition State Theory: Free-Energy Diagrams 251
6.8 The Stereochemistry of SN2 Reactions 253
6.9 The Reaction of tert-Butyl Chloride with Water:
An SN1 Reaction 256
6.10 A Mechanism for the SN1 Reaction 257
6.11 Carbocations 258
6.12 The Stereochemistry of SN1 Reactions 260
6.13 Factors Affecting the Rates of SN1 and SN2
Reactions 263
6.14 Organic Synthesis: Functional Group Transformations
Using SN2 Reactions 274
6.15 Elimination Reactions of Alkyl Halides 276
6.16 The E2 Reaction 280
6.17 The E1 Reaction 282
6.18 HOW TO Determine Whether Substitution
or Elimination
is Favored 283
6.19 Overall Summary 286
7
Alkenes and Alkynes I
Properties and Synthesis. Elimination
Reactions of Alkyl Halides 295
7.1 Introduction 295
7.2 The (E )–(Z ) System for Designating Alkene
Diastereomers 296
7.3 Relative Stabilities of Alkenes 297
7.4 Cycloalkenes 299
7.5 Synthesis of Alkenes via Elimination Reactions 300
7.6 Dehydrohalogenation of Alkyl Halides 300
7.7 Acid-Catalyzed Dehydration of Alcohols 306
7.8 Carbocation Stability and the Occurrence
of Molecular
Rearrangements 311
7.9 The Acidity of Terminal Alkynes 315
7.10 Synthesis of Alkynes by Elimination Reactions 316
7.11 Terminal Alkynes can be Converted to Nucleophiles
for Carbon–Carbon Bond Formation 318
7.12 Hydrogenation of Alkenes 320
7.13 Hydrogenation: The Function of the Catalyst 322
7.14 Hydrogenation of Alkynes 323
7.15 An Introduction to Organic Synthesis 325
8
Alkenes and Alkynes II
Addition Reactions 341
8.1 Addition Reactions of Alkenes 341
8.2 Electrophilic Addition of Hydrogen Halides to
Alkenes: Mechanism and Markovnikov’s Rule 343
8.3 Stereochemistry of the Ionic Addition to an Alkene 348
8.4 Addition of Water to Alkenes: Acid-Catalyzed
Hydration 348
8.5 Alcohols from Alkenes through Oxymercuration–
Demercuration: Markovnikov Addition 351
8.6 Alcohols from Alkenes through Hydroboration–Oxidation:
Anti-Markovnikov Syn Hydration 354
8.7 Hydroboration: Synthesis of Alkylboranes 355
8.8 Oxidation and Hydrolysis of Alkylboranes 357
8.9 Summary of Alkene Hydration Methods 360
8.10 Protonolysis of Alkylboranes 360
8.11 Electrophilic Addition of Bromine and
Chlorine to Alkenes 361
8.12 Stereospecific Reactions 363
8.13 Halohydrin Formation 365
8.14 Oxidation of Alkenes: Syn 1,2-Dihydroxylation 366
8.15 Oxidative Cleavage of Alkenes 368
8.16 Electrophilic Addition of Bromine
and Chlorine to Alkynes 372
8.17 Addition of Hydrogen Halides to Alkynes 373
8.18 Oxidative Cleavage of Alkynes 374
8.19 HOW TO Plan a Synthesis: Some Approaches
and Examples 374
8.20 Dimerization of Alkene 379
8.21 Prins Reaction 379
9
Radical Reactions 403
9.1 Introduction: How Radicals Form and
How they React 403
9.2 Homolytic Bond Dissociation Energies (DH °) 405
9.3 Reactions of Alkanes with Halogens 408
9.4 Chlorination of Methane: Mechanism of Reaction 410
9.5 Halogenation of Higher Alkanes 413
9.6 Reactions that Generate Tetrahedral Chirality
Centers 416
9.7 Allylic Substitution and Allylic Radicals 419
9.8 Benzylic Substitution and Benzylic Radicals 422
9.9 Radical Addition to Alkenes: The Anti-Markovnikov
Addition of Hydrogen Bromide 425
9.10 Other Important Radical Reactions 427
10
Alcohols and Ethers
Synthesis and Reactions 443
10.1 Structure and Nomenclature 443
10.2 Physical Properties of Alcohols and Ethers 446
10.3 Synthesis of Alcohols from Alkenes 446
10.4 Reactions of Alcohols 448
10.5 Alcohols as Acids 450
10.6 Conversion of Alcohols into Alkyl Halides 451
10.7 Alkyl Halides from the Reaction of Alcohols
with Hydrogen Halides 451
10.8 Alkyl Halides from the Reaction of Alcohols
with PBr3 or SOCl2 454
10.9 Tosylates, Mesylates, and Triflates: Leaving Group
Derivatives of Alcohols 456
10.10 Rearrangements 458
10.11 Synthesis of Ethers 461
10.12 Reactions of Ethers 466
10.13 Epoxides 468
10.14 Reactions of Epoxides 469
10.15 Anti 1,2-Dihydroxylation of Alkenes via
Epoxides 472
10.16 Crown Ethers 472
11
Alcohols from Carbonyl
Compounds 491
11.1 Structure of the Carbonyl Group 491
11.2 Oxidation–Reduction Reactions in Organic
Chemistry
493
11.3 Alcohols by Reduction of Carbonyl Compounds 494
11.4 Oxidation of Alcohols 497
11.5 Organometallic Compounds 502
11.6 Preparation of Organolithium and Organomagnesium
Compounds 502
11.7 Reactions of Organolithium and
Organomagnesium Compounds 504
11.8 Alcohols from Grignard Reagents 506
11.9 Lithium Dialkylcuprates: The Corey–Posner,
Whitesides–House Synthesis 519
12
Conjugated Unsaturated
Systems 535
12.1 Introduction 535
12.2 Alkadienes and Polyunsaturated Hydrocarbons 536
12.3 1,3-Butadiene: Electron Delocalization 537
12.4 Electrophilic Attack on Conjugated Dienes:
1,4-Addition 538
12.5 The Diels–Alder Reaction: A 1,4-Cycloaddition
Reaction
of Dienes 542
13
Aromatic Compounds 551
13.1 The Discovery of Benzene 551
13.2 Nomenclature of Benzene Derivatives 552
13.3 Reactions of Benzene 554
13.4 The Kekulé Structure for Benzene 555
13.5 The Thermodynamic Stability of Benzene 556
13.6 Modern Theories of the Structure of Benzene 557
13.7 Hückel’s Rule: The 4n + 2 o Electron Rule 560
13.8 Other Aromatic Compounds 565
13.9 Heterocyclic Aromatic Compounds 567
14
Reactions of Aromatic
Compounds 577
14.1 Electrophilic Aromatic Substitution Reactions 577
14.2 A General Mechanism for Electrophilic
Aromatic Substitution 578
14.3 Halogenation of Benzene 580
14.4 Nitration of Benzene 581
14.5 Sulfonation of Benzene 582
14.6 Friedel–Crafts Alkylation 583
14.7 Friedel–Crafts Acylation 585
14.8 Limitations of Friedel–Crafts Reactions 587
14.9 Synthetic Applications of Friedel–Crafts Acylations:
The Clemmensen and Wolff–Kishner Reductions
589
14.10 Substituents Can Affect Both the Reactivity of the
Ring and the Orientation of the Incoming Group 591
14.11 How Substituents Affect Electrophilic Aromatic
Substitution: A Closer Look 596
14.12 Reactions of the Side Chain of Alkylbenzenes 605
14.13 Alkenylbenzenes 607
14.14 Synthetic Applications 609
14.15 Allylic and Benzylic Halides in Nucleophilic
Substitution
Reactions 613
14.16 Reduction of Aromatic Compounds 614
15
Aldehydes and Ketones I.
Nucleophilic Addition to the
Carbonyl
Group 629
15.1 Introduction 629
15.2 Nomenclature of Aldehydes
and Ketones 629
15.3 Physical Properties 631
15.4 Synthesis of Aldehydes 632
15.5 Synthesis of Ketones 637
15.6 Nucleophilic Addition to the Carbon–Oxygen
Double Bond 639
15.7 The Addition of Alcohols: Hemiacetals and
Acetals 642
15.8 The Addition of Primary and Secondary Amines 650
15.9 The Addition of Hydrogen Cyanide:
Cyanohydrins 653
15.10 The Addition of Ylides: The Wittig Reaction 655
15.11 Oxidation of Aldehydes 658
15.12 The Baeyer–Villiger Oxidation 658
15.13 Chemical Analyses for Aldehydes and Ketones 663
16
Aldehydes and Ketones II.
Aldol Reactions 677
16.1 The Acidity of the ` Hydrogens
of Carbonyl Compounds:
Enolate Anions 677
16.2 Keto and Enol Tautomers 678
16.3 Reactions via Enols and Enolates 679
16.4 Aldol Reactions: Addition of Enolates and Enols
to Aldehydes and Ketones 685
16.5 Crossed Aldol Condensations 690
16.6 Cyclizations via Aldol Condensation 696
16.7 Lithium Enolates 697
17
Carboxylic Acids and Their
Derivatives 709
17.1 Introduction 709
17.2 Nomenclature and Physical Properties 710
17.3 Preparation of Carboxylic Acids 715
17.4 Acyl Substitution: Nucleophilic Addition–Elimination at
the Acyl Carbon 717
17.5 Acyl Chlorides 719
17.6 Carboxylic Acid Anhydrides 721
17.7 Esters 722
17.8 Amides 727
17.9 Derivatives of Carbonic Acid 733
17.10 Decarboxylation of Carboxylic Acids 735
17.11 Chemical Tests for Acyl Compounds 738
17.12 Summary of the Reactions of Carboxylic Acids
and Their Derivatives 741
18
Amines 751
18.1 Nomenclature 751
18.2 Physical Properties and Structure of Amines 753
18.3 Basicity of Amines: Amine Salts 754
18.4 Preparation of Amines 757
18.5 Reactions of Amines 765
18.6 Reactions of Amines with Nitrous Acid 767
18.7 Replacement Reactions of Arenediazonium Salts 769
18.8 Coupling Reactions of Arenediazonium Salts 772
18.9 Reactions of Amines with Sulfonyl Chlorides 774
18.10 Synthesis of Sulfa Drugs 775
18.11 Eliminations Involving Ammonium Compounds 776
18.12 The Cope Elimination 777
18.13 Summary of Preparations and Reactions of
Amines 777
19
Phenols and Aryl Halides 787
19.1 Structure and Nomenclature of Phenols 787
19.2 Naturally Occurring Phenols 788
19.3 Physical Properties of Phenols 789
19.4 Synthesis of Phenols 789
19.5 Reactions of Phenols as Acids 791
19.6 Other Reactions of the O—H Group of Phenols 794
19.7 Cleavage of Alkyl Aryl Ethers 795
19.8 Reactions of the Benzene Ring of Phenols 795
19.9 The Claisen Rearrangement 797
19.10 Quinones 798
19.11 Aryl Halides and Nucleophilic Aromatic Substitution 799
20
Carbohydrates 811
20.1 Introduction 811
20.2 Monosaccharides 814
20.3 Mutarotation 818
20.4 Glycoside Formation 819
20.5 Other Reactions of Monosaccharides 822
20.6 Oxidation Reactions of Monosaccharides 825
20.7 Reduction of Monosaccharides: Alditols 830
20.8 Reactions of Monosaccharides with Phenylhydrazine:
Osazones 831
20.9 Synthesis and Degradation of Monosaccharides 832
20.10 The d Family of Aldoses 833
20.11 Fischer’s Proof of the Configuration of d-(+)-
Glucose 833
20.12 Disaccharides 836
20.13 Polysaccharides 838
20.14 Other Biologically Important Sugars 843
20.15 Sugars that Contain Nitrogen 843
20.16 Carbohydrate Antibiotics 845
21
Amino Acids and Proteins 851
21.1 Introduction 851
21.2 Amino Acids 852
21.3 Synthesis of `-Amino Acids 858
21.4 Polypeptides and Proteins 860
21.5 Primary Structure of Polypeptides and
Proteins 862
21.6 Secondary, Tertiary, and Quaternary Structures
of Proteins 863
22
Carbene and
Carbenoids 871
22.1 Introduction 871
22.2 Existence of carbenes 871
22.3 Formation of Carbenes 871
22.4 Types of Carbenes 873
22.5 Reactions of Carbenes 873
22.6 Rearrangement in Carbenes 887
23
Reactions of Nitrene and
Electron Deficient Oxygen 897
23.1 Migration to Electron Deficient Nitrogen 897
23.2 Nitrene Formation 897
23.3 Hofmann—Curtius—Lossen—Schmidt Group
of Rearrangements 898
23.4 Curtius Reaction 899
23.5 Schmidt Reaction 899
23.6 Hofmann-Bromamide Reaction or Hofman
Rearrangement 900
23.7 Beckmann Rearrangement 902
23.8 Stieglitz Rearrangement 904
Appendix A A-1
JEE Main 2025 Questions with Solutions P-1
JEE Advanced / Multidisciplinary PYQs
with Answers and Solutions Q-1
Index I-1
Index—QR Codes I-23