Pharmaceutical Organic Chemistry - 1st Edition - ISBN: 9788131228005, 9788131232675

Pharmaceutical Organic Chemistry

1st Edition

Authors: S.K. Bhasin Reena Gupta
eBook ISBN: 9788131232675
Paperback ISBN: 9788131228005
Imprint: Elsevier
Published Date: 19th March 2012
Page Count: 812
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Description

Pharmaceutical Organic Chemistry has been written keeping in mind the severe need for a comprehensive text to meet the curriculum needs of the undergraduate pharmacy students. It not only provides all the curriculum topics to the students but also contains all the vital reactions/mechanisms that the students look for in an organic chemistry book.

Key Features

  1. Entire subject matter has been written in a systematic and lucid style in simple language.
  2. All the basic concepts and fundamentals of organic chemistry have been explained with well-chosen examples.
  3. For better understanding of the subject matter, important points have been highlighted in the form of the textboxes titled as Remember, Learning Plus and Noteworthy Points, wherever required.
  4. Summary of the topics in the form of Memory Focus has been given at relevant places to help the students to revise the subject matter quickly.
  5. Stepwise mechanism of the reactions as per the syllabus has been illustrated, laying emphasis on the reactive intermediates involved.
  6. At the end of each chapter, Revision Questions including descriptive questions and short answer questions have been given for the students to practice.

Multiple Choice Questions with answers have been included at the end of each chapter.

Table of Contents

Contents

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 Configuration 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) Molecular Orbitals 040

1.12 Comparison of Valence Bond Theory and Molecular Orbital Theory 042

1.13 Hybridization 043

1.14 Intermolecular Forces 053

1.15 Hydrogen Bonding 056

1.16 Bond Dissociation Energies 063

Part C: Acids and Bases

1.17 Introduction 071

1.18 Arrhenius Concept of Acids and Bases 071

1.19 Bronsted-Lowry Concept of Acids and Bases 073

1.20 Lewis Concept of Acids and Bases 077

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 Modifications 155

3.15 Specification of Configuration 156

3.16 Specification of Configuration by R and S Notations 161

3.17 Geometrical Isomerism 166

3.18 Conformation of Alkanes 175

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

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 Classification of Alkynes 260

6.6 Commercial Methods of Preparation of Acetylene 261

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

6.11 Addition Reactions 264

6.12 Addition of Hydrogen 264

6.13 Electrophilic Additions 266

6.14 Nucleophilic Addition Reactions 271

6.15 Acidity of Acetylenic Hydrogen 272

6.16 Oxidation Reaction of Alkynes 274

6.17 Polymerization 276

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

 

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 Influence of Groups in Electrophilic Substitution 347

CHAPTER 10 ARENES

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 Classification 393

11.3 Isomerism in Alkyl Halides 396

11.4 General Methods of Preparation of Alkyl Halides 397

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 Classification of Alcohols 427

12.3 Isomerism 429

12.4 General Methods of Preparation of Alcohols 431

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 Classification 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

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

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 Classification 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

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

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

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

19.4 Acetoacetic Ester 677

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 Classification of Organic Reactions 717

20.8 Substitution Reactions 718

20.9 Addition Reactions 721

20.10 Elimination Reactions 723

20.11 Rearrangement Reactions 724

CHAPTER 21 ELECTROCYCLIC AND SIGMATROPIC REARRANGEMENTS

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 Classification 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

Details

No. of pages:
812
Language:
English
Copyright:
© Elsevier 2012
Published:
Imprint:
Elsevier
eBook ISBN:
9788131232675
Paperback ISBN:
9788131228005

About the Author

S.K. Bhasin

He is the corresponding author.

Reena Gupta