Fundamentals of. Organic Chemistry. for. [Second Year B.Sc. (Main) Students of M.G. University, Kerala] III Semester

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1 Fundamentals of Organic Chemistry for [Second Year B.Sc. (Main) Students of M.G. University, Kerala] III Semester (This Book is an outcome of Modern Organic Chemistry by M.K. Jain & S.C. Sharma duly recommended by M.G. University.) M.K. JAIN S.C. SHARMA M.Sc., Ph. D. (Glasgow) M.Sc., Ph.D. Former, Professor, Former-Head Deptt. of Chemistry National Dairy Research Institute V.B.R.I. P.G. College, (Deemed University), KARNAL (Haryana) UDAIPUR (Rajasthan) Future for WINNERS VISHAL PUBLISHING CO. JALANDHAR DELHI

2 CONTENTS Chapter No. Title Page No. Chapter No. Title Page No. 1. CLASSIFICATION & IUPAC NOMENCLATURE OF ORGANIC COMPOUNDS* Classification IUPAC or Geneva names Rules of IUPAC system of nomenclature for acyclic compounds IUPAC system of nomenclature for substituted alkanes Alkenes, alkynes and substituents IUpac nomenclature of cycloalkanes and its derivatives IUPAC nomenclature of bicycloalkanes and related compounds IUPAC nomenclature of bicyclic spiro compounds IUPAC nomenclature of alkyl halides IUPAC nomenclature of alcohols IUPAC nomenclature of phenols IUPAC nomenclature of aldehydes and ketones IUPAC nomenclature of acids IUPAC nomenclature of acid derivatives IUPAC nomenclature of amines IUPAC nomenclature of nitro compounds Procedure for writing the structure of a compound with a given IUPAC name 18 Questions FUNDAMENTALS OF ORGANIC REACTION MECHANISM-I Introduction Notations used to show Electron Migration Curved arrow notation Double Headed Arrow(s) Half-headed Arrow (Fish hook arrow) Types of reagents Nucleophiles Electrophiles Free radicals Types of organic reactions 25 [A] Substitution reactions 25 [B] Addition reactions 26 [C] Elimination reactions 27 [D] Rearrangement reactions Homolytic and Heterolytic Cleavage of a covalent bond (formation of reactive intermediates) Carbocations / Carbonium ions Carbanions Free Radicals Electron Displacement effects Inductive or inductometric Effect Electromeric Effect Resonance and Resonance Effect Resonance theory Mesomeric effect Hyperconjugation Steric effects / Inhibition / Hindrance 49 Questions FUNDAMENTALS OF ORGANIC REACTION MECHANISM-II Introduction Addition Reactions Electrophilic Additions to double bond Polymerisation Types of Polymerisation Reactions Aliphatic Substitution Reactions Detailed Mechanisms Of aliphatic Nucleophilic Substitution Reactions 66

3 Chapter No. Title Page No. Chapter No. Title Page No. 2. Factors Influencing Rates Of aliphatic Nucleophilic Substitution Reactions S N 1 vs. S N 2 Mechanisms Elimination Reactions Mechanisms Of Elimination Reactions Orientation In Elimination Reactions (hofmann & saytzeff elimination) Substitution vs. Elimination 77 Questions STEREOCHEMISTRY-I Introduction Stereoisomerism Types of Stereoisomers General Stereochemistry Concept of Chirality Tetrahedral Carbon Chirality and Enantiomerism Wedge and Dashed Bond Drawing of Organic Molecules (Perspective Drawings) Asymmetric Carbon Atom and Related Terms Elements of symmetry The Asymmetric Carbon Atoms And Molecular Chirality Optical activity Acyclic molecules with one asymmetric/chiral carbon or stereogenic centre Enantiomers And Related Aspects Properties of Enantiomers The Racemic Modification Configuration Relative Specification of Configuration D and L * Notation Specification of Configuration R and S notation Compounds with two Stereogenic Centres or two asymmetric/chiral carbon Properties of Diastereomers Distinction Between Diastereomers And Enantiomers Fischer projections Specifying R S Configurations on Fischer Projection Erythro and threo nomenclature (notation) of configurations Resolution Asymmetric (Stereogenic Centre) Synthesis Walden Inversion Retention and racemisation STEREOCHEMISTRY-II Geometric isomerism (cis-trans isomerism) Concept of Hindered Rotation About a Carbon-Carbon Double Bond and Geometric Isomerism Geometric Isomers as Diastereomers Structure of Alkenes and Geometric Isomerism Extended Scope of Geometric Isomerism Assigning Configuration to Geometric Isomers E-Z System of Nomenclature for Cis-trans Isomers Relative Stabilities of cis-trans Isomers Conformation Of Alkanes (conformational analysis) Factors Influencing Conformational Stability Conformational Analysis Of Cyclohexane Axial And Equatorial Bonds* In Cyclohexane 122

4 Chapter No. Title Page No. Chapter No. Title Page No. 2. 1, 3-Diaxial Interactions In Cyclohexane Derivatives Conformational Isomers vs Configurational Isomers 123 Questions ARENES AND AROMATICITY Introduction Structure Of Benzene Aromatic Sextet And Orbital Picture Resonance And Molecular Orbital Structure Of Naphthalene 133 I. Resonance Structure Resonance and M.O. Structure of Anthracene 135 (1) Resonance Structure. 135 (2) Molecular Orbital Structure Concept Of Aromaticity Aromaticity/Aromatic Character Hückel Theory Of Aromaticity 136 (1) Benzenoids 137 (2) Non-Benzenoid Aromatic Compounds/ Ions Electrophilic Aromatic Substitution Reactions General Pattern Of Electrophilic Aromatic Substitution Reactivity Of Naphthalene 143 Questions Bimolecular Displacement Mechanism Benzyne Intermediate Mechanism (Elimination Addition Mechanism) 160 Questions PERICYCLIC REACTIONS Introduction Salient features of Pericyclic reactions Classification of Pericyclic reactions Electrocyclic reactions Cycloaddition reactions (Diels-Alder reaction) Sigmatropic rearrangements The Frontier orbital method 172 Questions 173 Model Question Papers University Question Paper ORIENTATION OF SUBSTITUTION IN ARENES Introduction Orientation Electrophilic Aromatic Substitution Reactions Effect Of Activating Groups Effect Of Deactivating Groups Nucleophilic Aromatic Substitution Mechanisms 157

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