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Co ntents
Preface v
CHAPTER 1 STRUCTURE AND PROPERTIES
Part A: Wave Mechanical Model of Atom
1.1 Introduction 001
1.2 Wave Mechanical Model of Atom (Atomic Orbitals) 002
1.3 Quantum Numbers 005
1.4 Shapes of Orbitals 011
1.5 Rules for Filling of Orbitals or Electronic Conguration of Atoms 016
1.6 Extra Stability of Half-Filled and Completely Filled Subshells 021
Part B: Formation of Molecules
1.7 Introduction 029
1.8 Valence Bond (VB) Theory 030
1.9 Molecular Orbital (MO) Theory 033
1.10 Formation of Bonding and Antibonding Molecular
Orbitals (LCAO Method) 037
1.11 Combination of Atomic Orbitals–Sigma (s) and Pi (π)
1.12
1.13
1.14
1.15
1.16
Part C:
1.17
1.18
Molecular Orbitals
Comparison of Valence Bond Theory and Molecular Orbital Theory 042
Hybridization 043
Intermolecular Forces 053
Hydrogen Bonding 056
Bond Dissociation Energies 063
Acids and Bases
Introduction 071
Arrhenius Concept of Acids and Bases 071
040
x
CO N T E N T S
1.19 Bronsted-Lowry Concept of Acids and Bases 073
Lewis Concept of Acids and Bases 077
1.20
CHAPTER 2 NOMENCLATURE OF ORGANIC COMPOUNDS
2.1 Introduction 091
2.2 IUPAC Nomenclature of Organic Compounds 092
2.3 General Rules of IUPAC System 093
2.4 Nomenclature of Hydrocarbons 097
2.5 IUPAC Nomenclature of Compounds Containing One Functional
Group, Multiple Bonds and Substituent 105
2.6 Nomenclature of Polyfunctional Compounds 108
2.7 Nomenclature of Substituted Alicyclic Compounds Having Some
Functional Group Along with Other Substituents 115
2.8 Nomenclature of Aromatic Compounds 116
CHAPTER 3 STEREOCHEMISTRY
3.1 Introduction 133
3.2 Isomerism 133
3.3 Structural Isomerism 135
3.4 Stereoisomerism 138
3.5 Optical Isomerism 138
3.6 Concept of Chirality 140
3.7 Types of Optical Isomers 143
3.8 Planar Representation of Three-Dimensional Formulae: Fischer
Projection Formulae 145
3.9 Diastereomerism: Compounds Having More than One Chiral Carbon 148
3.10
Meso Compounds 150
3.11 Number of Possible Stereoisomers in Compounds Containing
Different Number of Chiral Centres 152
3.12 Racemization 153
3.13
Internal and External Compensation 153
3.14
Resolution of Racemic Modications 155
CO N T E N T S
3.15 Specication of Conguration 156
3.16
Specication of Conguration by R and S Notations 161
3.17
Geometrical Isomerism 166
Conformation of Alkanes 175
3.18
CHAPTER 4 ALKANES
4.1 Introduction 189
4.2 Structure of Alkanes 189
4.3 Structural Isomerism 191
4.4 General Methods of Preparation of Alkanes 192
4.5 Physical Properties of Alkanes 200
4.6 Chemical Properties of Alkanes 202
4.7 Mechanism of Halogenation 208
xi
CHAPTER 5 ALKENES
5.1 Introduction 217
5.2 Structure of Alkenes (Structure of Carbon–Carbon
Double Bond) 217
5.3 Nomenclature of Alkenes 219
5.4 Isomerism in Alkenes 220
5.5 Method of Preparation of Alkenes 221
5.6 Physical Properties of Alkenes 230
5.7 Chemical Properties of Alkenes 231
CHAPTER 6 ALKYNES
6.1 Introduction 257
6.2 Structure of Alkynes (Carbon–Carbon Triple Bond) 257
6.3 Isomerism in Alkynes 258
6.4 Nomenclature of Alkynes (Acetylenes) 259
6.5 Classication of Alkynes 260
6.6 Commercial Methods of Preparation of Acetylene 261
xii
CO N T E N T S
6.7 General Methods of Preparation of Alkynes 261
6.8 Physical Properties of Alkynes 263
6.9 Chemical Properties of Alkynes 263
6.10 Low Reactivity of Alkynes Towards Electrophilic
Addition Reactions 264
Addition Reactions 264
6.11
Addition of Hydrogen 264
6.12
Electrophilic Additions 266
6.13
Nucleophilic Addition Reactions 271
6.14
Acidity of Acetylenic Hydrogen 272
6.15
Oxidation Reaction of Alkynes 274
6.16
Polymerization 276
6.17
6.18
Distinction between Alkane, Alkene and Alkyne 277
CHAPTER 7 CYCLOALKANES
7.1 Introduction 285
7.2 Nomenclature of Cycloalkanes 285
7.3 Preparation of Cycloalkanes 289
7.4 Physical Properties 295
7.5 Chemical Properties 296
7.6 Relative Stability of Cycloalkanes (Baeyer’s Strain Theory) 298
7.7 Heat of Combustion and Stability of Cycloalkanes 299
7.8 Sachse–Mohr Theory of Strainless Rings 300
CHAPTER 8 DIENES
8.1 Introduction 307
8.2 Nomenclature 308
8.3 Methods of Preparation of Conjugated Dienes 308
8.4 Relative Stability of Conjugated Dienes 309
8.5 Chemical Properties of Conjugated Dienes 312
CO N T E N T S
CHAPTER 9 BENZENE AND POLYNUCLEAR COMPOUNDS
9.1 Introduction 325
9.2 Nomenclature of Aromatic Compounds 325
9.3 Isomerism of Benzene Derivatives 328
9.4 Preparation of Benzene 329
9.5 Properties of Benzene 331
9.6 Structure of Benzene 337
9.7 Aromatic Electrophilic Substitution (Characteristic
Aromatic Reaction) 339
9.8 Theory of Reactivity 345
9.9 Directive Inuence of Groups in Electrophilic Substitution 347
CHAPTER 10 ARENES
xiii
10.1 Introduction 359
10.2 Structure and Nomenclature of Arenes 359
10.3 Isomerism in Arenes 363
10.4 The Aromatic Character (Aromaticity) 364
10.5 Preparation of Arenes 367
10.6 Physical Properties 370
10.7 Chemical Properties 370
10.8 Ortho-Para Ratio in the Formation of Disubstitution Derivatives 378
10.9 Orientation in Disubstituted Benzene
(Introduction of a Third Group in Benzene Ring) 380
10.10 Some Individual Members 382
CHAPTER 11 ALKYL HALIDES
11.1 Introduction 393
11.2 Classication 393
11.3 Isomerism in Alkyl Halides 396
11.4 General Methods of Preparation of Alkyl Halides 397
xiv
11.5 Polar Nature of Alkyl Halides 402
11.6 Physical Properties 403
11.7 Chemical Properties 404
11.8 Nucleophilic Substitution Reactions 408
11.9 Elimination Reactions 414
11.10
Miscellaneous Reactions 416
11.11
Uses of Alkyl Halides 420
CHAPTER 12 ALCOHOLS
12.1 Introduction 427
12.2 Classication of Alcohols 427
12.3 Isomerism 429
12.4 General Methods of Preparation of Alcohols 431
CO N T E N T S
12.5 Structure of Alcohol 438
12.6 Physical Properties 439
12.7 Chemical Properties 440
12.8 Distinction Between 1°, 2° and 3° Alcohols 452
12.9 Ethylene Glycol 456
12.10
Glycerol (1,2,3-Propanetriol) 465
CHAPTER 13 PHENOLS
13.1 Introduction 483
13.2 Classication and Nomenclature of Phenols 484
13.3 Preparation of Phenols 485
13.4 Physical Properties 487
13.5 Chemical Properties 488
13.6 Uses of Phenol 501
13.7 Distinction Between Alcohols and Phenols 502
13.8 Effects of Phenol on Human Health 502
CO N T E N T S
CHAPTER 14 ETHERS AND EPOXIDES
14.1 Introduction 509
14.2 Nomenclature 510
14.3 Isomerism 511
14.4 Structure of Ethers 512
14.5 Preparation of Ethers 513
14.6 Physical Properties 516
14.7 Chemical Properties 517
14.8 Uses of Ether 519
14.9 Epoxide 519
14.10 Structure of Epoxides 520
14.11 Preparation of Epoxides 520
14.12 Reactions of Epoxides 521
xv
14.13 Physiological Effects of Ethylene Oxide 524
14.14 Acid-Catalysed Cleavage 525
14.15 Base-Catalysed Cleavage 526
14.16 Orientation Cleavage 526
CHAPTER 15 AMINES
15.1 Introduction 533
15.2 Classication of Amines 533
15.3 Structure of Amine 535
15.4 Nomenclature of Amines 535
15.5 Isomerism of Amines 538
15.6 Preparation of Amines 540
15.7 Separation of Primary, Secondary and Tertiary Amines 544
15.8 Physical Properties 546
15.9 Stereochemistry of Amines 547
15.10 Chemical Properties 547
xvi
15.11 Distinction Between Primary, Secondary and Tertiary Amines 561
15.12 Tests for Amines 561
15.13 Uses 562
CHAPTER 16 ALDEHYDES AND KETONES
16.1 Introduction 569
16.2 Nomenclature 569
16.3 Isomerism 571
16.4 Structure of Carbonyl Group 572
16.5 Methods of Preparation 573
16.6 Methods of Preparation of Aromatic Aldehydes and Ketones 578
16.7 Physical Properties of Carbonyl Compounds 580
16.8 Chemical Properties of Carbonyl Compounds 581
16.9 Distinction Between Aldehydes and Ketones 596
CO N T E N T S
16.10 Uses of Aldehydes and Ketones 596
CHAPTER 17 CARBOXYLIC ACIDS
17.1 Introduction 605
17.2 Nomenclature of Carboxylic Acids 606
17.3 Isomerism 608
17.4 Structure of Carboxyl Group 609
17.5 Methods of Preparation 610
17.6 Physical Properties of Carboxylic Acids 612
17.7 Chemical Properties 613
17.8 Effect of Substituents on Acidity 620
17.9 Some Commercially Important Carboxylic Acids 622
CHAPTER 18 FUNCTIONAL DERIVATIVES OF CARBOXYLIC ACID
18.1 Introduction 631
18.2 Nomenclature and Isomerism in Acid Derivatives 632
CO N T E N T S
18.3 Preparation and Reactions of Acid Chlorides 635
18.4 Preparation and Reactions of Acid Amides 641
18.5 Preparation and Reactions of Acid Anhydrides 645
18.6 Preparation and Reactions of Acid Esters 648
18.7 Nucleophilic Acyl Substitution 651
18.8 Acidic and Alkaline Hydrolysis of Acid Derivatives 656
CHAPTER 19 ACTIVE METHYLENE COMPOUNDS
19.1 Introduction 667
19.2 Preparation of Malonic Ester 668
19.3 Properties of Malonic Ester 668
xvii
19.4 Acetoacetic Ester
19.5 Properties of Acetoacetic Ester 678
19.6 Keto–Enol Tautomerism 684
19.7 Relative Stabilities of Keto–Enol Forms 685
19.8 Keto–Enol Tautomerism in Acetoacetic Ester 686
CHAPTER 20 MECHANISM OF ORGANIC REACTIONS
20.1 Introduction 691
20.2 Cleavage of Bond 692
20.3 Types of Reagents 693
20.4 Electronic Effects in Covalent Bonds 694
20.5 Hyperconjugation or No-Bond Resonance 705
20.6 Reaction Intermediates 710
20.7 Classication of Organic Reactions 717
20.8 Substitution Reactions 718
677
20.9 Addition Reactions 721
20.10 Elimination Reactions 723
20.11 Rearrangement Reactions 724
xviii
CHAPTER 21 ELECTROCYCLIC AND SIGMATROPIC REARRANGEMENTS
CO N T E N T S
21.1 Introduction 731
21.2 Stereochemistry of Electrocyclic Reactions 732
21.3 Conrotatory and Disrotatory Motions (Ring-Opening and Ring-Closing Reactions) 735
21.4 Sigmatropic Rearrangement 739
21.5 Classication of Sigmatropic Rearrangements 740
21.6 Suprafacial and Antarafacial Sigmatropic Shift 741
21.7 Cope and Claisen Rearrangement 742
21.8 Migration of Carbon in Sigmatropic Rearrangement 744
CHAPTER 22 BIOMOLECULES
22.1 Introduction 751
22.2 Carbohydrates 751
22.3 Proteins 762
22.4 Enzymes 774
22.5 Nucleic Acids 777
22.6 Lipids 783
Index 793