A Textbook of Organic Chemistry – Volume 1

Title: A Textbook of Organic Chemistry – Volume 1
Author: Mandeep Dalal
ISBN: 8195242731, 9788195242733 (Paperback)
Publisher: Dalal Institute
Edition: First
Number of Pages: 448
Physical Dimensions: 7.44 × 9.69 inch

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DESCRIPTION
An advanced-level textbook of organic chemistry for the graduate (B.Sc) and postgraduate (M.Sc) students of Indian and foreign universities. This book is a part of the four-volume series, entitled “A Textbook of Organic Chemistry – Volume I, II, III, IV”.

Table of Contents

• CHAPTER 1: Nature of Bonding in Organic Molecules
  • Delocalized Chemical Bonding
  • Conjugation
  • Cross Conjugation
  • Resonance
  • Hyperconjugation
  • Tautomerism
  • Aromaticity in Benzenoid and Nonbenzenoid Compounds
  • Alternant and Non-Alternant Hydrocarbons
  • Huckel’s Rule: Energy Level of π-Molecular Orbitals
  • Annulenes
  • Antiaromaticity
  • Homo-Aromaticity
  • PMO Approach
  • Bonds Weaker than Covalent
  • Addition Compounds: Crown Ether Complexes and Cryptands, Inclusion Compounds, Cyclodextrins
  • Catenanes and Rotaxanes
  • Problems
  • Bibliography
• CHAPTER 2: Stereochemistry
  • Chirality
  • Elements of Symmetry
  • Molecules with More Than One Chiral Centre: Diastereomerism
  • Determination of Relative and Absolute Configuration (Octant Rule Excluded) with Special Reference to Lactic Acid, Alanine & Mandelic Acid
  • Methods of Resolution
  • Optical Purity
  • Prochirality
  • Enantiotopic and Diastereotopic Atoms, Groups and Faces
  • Asymmetric Synthesis: Cram’s Rule and Its Modifications, Prelog’s Rule
  • Conformational Analysis of Cycloalkanes (Upto Six Membered Rings)
  • Decalins
  • Conformations of Sugars
  • Optical Activity in Absence of Chiral Carbon (Biphenyls, Allenes and Spiranes)
  • Chirality Due to Helical Shape
  • Geometrical Isomerism in Alkenes and Oximes
  • Methods of Determining the Configuration
  • Problems
  • Bibliography
• CHAPTER 3: Reaction Mechanism: Structure and Reactivity
  • Types of Mechanisms
  • Types of Reactions
  • Thermodynamic and Kinetic Requirements
  • Kinetic and Thermodynamic Control
  • Hammond’s Postulate
  • Curtin-Hammett Principle
  • Potential Energy Diagrams: Transition States and Intermediates
  • Methods of Determining Mechanisms
  • Isotope Effects
  • Hard and Soft Acids and Bases
  • Generation, Structure, Stability and Reactivity of Carbocations, Carbanions, Free Radicals, Carbenes and Nitrenes
  • Effect of Structure on Reactivity
  • The Hammett Equation and Linear Free Energy Relationship
  • Substituent and Reaction Constants
  • Taft Equation
  • Problems
  • Bibliography
• CHAPTER 4: Carbohydrates
  • Types of Naturally Occurring Sugars
  • Deoxy Sugars
  • Amino Sugars
  • Branch Chain Sugars
  • General Methods of Determination of Structure and Ring Size of Sugars with Particular Reference to Maltose, Lactose, Sucrose, Starch and Cellulose
  • Problems
  • Bibliography
• CHAPTER 5: Natural and Synthetic Dyes
  • Various Classes of Synthetic Dyes Including Heterocyclic Dyes
  • Interaction Between Dyes and Fibers
  • Structure Elucidation of Indigo and Alizarin
  • Problems
  • Bibliography
• CHAPTER 6: Aliphatic Nucleophilic Substitution
  • The SN2, SN1, Mixed SN1 and SN2, SNi, SN1′, SN2′, SNi′ and SET Mechanisms
  • The Neighbouring Group Mechanisms
  • Neighbouring Group Participation by π and σ Bonds
  • Anchimeric Assistance
  • Classical and Nonclassical Carbocations
  • Phenonium Ions
  • Common Carbocation Rearrangements
  • Applications of NMR Spectroscopy in the Detection of Carbocations
  • Reactivity – Effects of Substrate Structure, Attacking Nucleophile, Leaving Group and Reaction Medium
  • Ambident Nucleophiles and Regioselectivity
  • Phase Transfer Catalysis
  • Problems
  • Bibliography
• CHAPTER 7: Aliphatic Electrophilic Substitution
  • Bimolecular Mechanisms − SE2 and SEi
  • The SE1 Mechanism
  • Electrophilic Substitution Accompanied by Double Bond Shifts
  • Effect of Substrates, Leaving Group and the Solvent Polarity on the Reactivity
  • Problems
  • Bibliography
• CHAPTER 8: Aromatic Electrophilic Substitution
  • The Arenium Ion Mechanism
  • Orientation and Reactivity
  • Energy Profile Diagrams
  • The Ortho/Para Ratio
  • ipso-Attack
  • Orientation in Other Ring Systems
  • Quantitative Treatment of Reactivity in Substrates and Electrophiles
  • Diazonium Coupling
  • Vilsmeier Reaction
  • Gattermann-Koch Reaction
  • Problems
  • Bibliography
• CHAPTER 9: Aromatic Nucleophilic Substitution
  • The ArSN1, ArSN2, Benzyne and SRN1 Mechanisms
  • Reactivity – Effect of Substrate Structure, Leaving Group and Attacking Nucleophile
  • The von Richter, Sommelet-Hauser, and Smiles Rearrangements
  • Problems
  • Bibliography
• CHAPTER 10: Elimination Reactions
  • The E2, E1 and E1CB Mechanisms
  • Orientation of the Double Bond
  • Reactivity – Effects of Substrate Structures, Attacking Base, the Leaving Group and The Medium
  • Mechanism and Orientation in Pyrolytic Elimination
  • Problems
  • Bibliography
• CHAPTER 11: Addition to Carbon-Carbon Multiple Bonds
  • Mechanistic and Stereochemical Aspects of Addition Reactions Involving Electrophiles, Nucleophiles and Free Radicals
  • Regio- and Chemoselectivity: Orientation and Reactivity
  • Addition to Cyclopropane Ring
  • Hydrogenation of Double and Triple Bonds
  • Hydrogenation of Aromatic Rings
  • Hydroboration
  • Michael reaction
  • Sharpless Asymmetric Epoxidation
  • Problems
  • Bibliography
• CHAPTER 12: Addition to Carbon-Hetero Multiple Bonds
  • Mechanism of Metal Hydride Reduction of Saturated and Unsaturated Carbonyl Compounds, Acids, Esters and Nitriles
  • Addition of Grignard Reagents, Organozinc and Organolithium Reagents to Carbonyl and Unsaturated Carbonyl Compounds
  • Wittig Reaction
  • Mechanism of Condensation Reactions Involving Enolates: Aldol, Knoevenagel, Claisen, Mannich, Benzoin, Perkin and Stobbe Reactions
  • Hydrolysis of Esters and Amides
  • Ammonolysis of Esters
  • Problems
  • Bibliography
• INDEX