Description
Wiley Wiley'S Solomons, Fryhle & Snyder Organic Chemistry For Jee (Main & Advanced), 3Ed, 2019 by M S CHOUHAN
This adapted version of one of the world's most well-known books on Organic Chemistry combines the Solomons, Fryhle and Synder approach to Organic Chemistry with engineering entrance examinations requirements. The book has been reorganized based on the challenges faced by the students preparing for engineering entrance in terms of practice problems and clarity of theories. The relevance to exams is enhanced by elaborating concepts related to the syllabus, removing irrelevant topics and addition of specific problems at the end of each chapter.
About the Author
M.S. Chouhan is currently the Director and HOD (Organic Chemistry) of Vibrant Academy at Kota, Rajasthan. His earlier designations include Senior Faculty (Organic Chemistry) for Bansal Classes at Kota, Rajasthan. He had earned his graduate and postgraduate degrees in Chemistry from Mumbai University. Apart from these he also has a Diploma in Biotechnology. He has over 10 years of experience in training engineering aspirants and there have been about 15000 students under his guidance. His easy-to understand-approach and stepwise problem-solving methods help them master their basic skills and enhance their ability to solve all types of questions asked in NEETI & JEE (Advanced) unaffected by the ever-changing pattern of the examination.
Table of Contents
Chapter 1 The Basics: Bonding and Molecular Structure
1.1 Development of the Science of Organic Chemistry
1.2 Atomic Structure
1.3 The Structural Theory of Organic Chemistry
1.4 Chemical Bonds: The Octet Rule
1.5 Resonance Theory
1.6 Hyperconjugation
1.7 The Structure of Methane and Ethane: sp3 Hybridization
1.8 The Structure of Ethene (Ethylene): sp2 Hybridization
1.9 The Structure of Ethyne (Acetylene): sp Hybridization
1.10How to Interpret and Write Structural Formulas
Chapter 2: Families of Carbon Compounds, Functional Groups and Intermolecular Forces
2.1 Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds
2.2 Polar and Nonpolar Molecules
2.3 Functional Groups
2.4 Alkyl Halides or Haloalkanes
2.5 Alcohols
2.6 Ethers
2.7 Amines
2.8 Aldehydes and Ketones
2.9 Carboxylic Acids, Esters, and Amides
2.10 Nitriles
2.11 Summary of Important Families of Organic Compounds
2.12 Physical Properties and Molecular Structure
2.13 Summary of Attractive Electric Forces
Chapter 3: An Introduction to Organic Reactions and Their Mechanisms: Acids and Bases
3.1 Reactions and Their Mechanisms
3.2 Acid–Base Reactions
3.3 Lewis Acids and Bases
3.4 Heterolysis of Bonds to Carbon: Carbocations and Carbanions
3.5 How to Use Curved Arrows in Illustrating Reactions
3.6 The Strength of Brønsted– Lowry Acids and Bases: Ka and pKa
3.7 How to Predict the Outcome of Acid–Base Reactions
3.8 Relationships between Structure and Acidity
3.9 Energy Changes
3.10 The Relationship between the Equilibrium Constant and the Standard Free-Energy Change, DG°
3.11 The Acidity of Carboxylic Acids versus Alcohols
3.12 The Effect of the Solvent on Acidity
3.13 Organic Compounds as Bases
3.14 Acids and Bases in Nonaqueous Solutions
3.15 Acid–Base Reactions and the Synthesis of Deuterium-and Tritium-Labeled Compounds
3.16 Reaction of NaHCO3
3.17 Steric Inhibition of Resonance (SIR) Effect
3.18 Ortho and Para Effects
Chapter 4 : Stereochemistry Chiral Molecules
4.1 Chirality and Stereochemistry
4.2 Isomerism: Constitutional Isomers and Stereoisomers
4.3 Enantiomers and Chiral Molecules
4.4 A Single Chirality Center Causes a Molecule to Be Chiral
4.5 More about the Biological Importance of Chirality
4.6 How to Test for Chirality: Planes of Symmetry
4.7 Naming Enantiomers: The R,S-System
4.8 Properties of Enantiomers: Optical Activity
4.9 The Origin of Optical Activity
4.10 The Synthesis of Chiral Molecules
4.11 Chiral Drugs
4.12 Molecules with More than One Chirality Center
4.13 Fischer Projection Formulas
4.14 Stereoisomerism of Cyclic Compounds
4.15 Relating Configurations through Reactions in Which No Bonds to the Chirality Center Are Broken
4.16 Separation of Enantiomers: Resolution
4.17 Compounds with Chirality Centers Other than Carbon
4.18 Chiral Molecules That Do Not Possess a Chirality Center
4.19 Biphenyl
4.20 Racemization of Biphenyl Compounds
4.21 Tautomerism
4.22 Gero Entropy
Chapter 5 : Nomenclature and Conformations of Alkanes and Cycloalkanes
5.1 Introduction to Alkanes and Cycloalkanes
5.2 Shapes of Alkanes
5.3 HOW TO Name Alkanes, Alkyl Halides, and Alcohols: The IUPAC System
5.4 HOW TO Name Cycloalkanes
5.5 HOW TO Name Alkenes and Cycloalkenes
5.6 HOW TO Name Alkynes
5.7 Physical Properties of Alkanes and Cycloalkanes
5.8 Sigma Bonds and Bond Rotation
5.9 Conformational Analysis of Butane
5.10 The Relative Stabilities of Cycloalkanes: Ring Strain
5.11 Conformations of Cyclohexane: The Chair and the Boat
5.12 Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups
5.13 Disubstituted Cycloalkanes: cis–trans Isomerism
5.14 Bicyclic and Polycyclic Alkanes
5.15 Chemical Reactions of Alkanes
5.16 Synthesis of Alkanes and Cycloalkanes
5.17 HOW TO Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency
5.18 Applications of Basic Principles
Chapter 6 Ionic Reactions—Nucleophilic Substitution and Elimination Reactions of Alkyl Halides
6.1 Alkyl Halides
6.2 Nucleophilic Substitution Reactions
6.3 Nucleophiles
6.4 Leaving Groups
6.5 Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction
6.6 A Mechanism for the SN2 Reaction
6.7 Transition State Theory: Free- Energy Diagrams
6.8 The Stereochemistry of SN2 Reactions
6.9 The Reaction of tert-butyl Chloride with Water: an SN1 Reaction
6.10 A Mechanism for the SN1 Reaction
6.11 Carbocations
6.12 The Stereochemistry of SN1 Reactions
6.13 Factors Affecting the Rates of SN1 and SN2 Reactions
6.14 Organic Synthesis: Functional Group Transformations Using SN2 Reactions
6.15 Elimination Reactions of Alkyl Halides
6.16 The E2 Reaction
6.17 The E1 Reaction
6.18 HOW TO Determine Whether Substitution or Elimination is Favored
6.19 Overall Summary
Chapter 7 Alkenes and Alkynes I: Properties and Synthesis. Elimination Reactions of Alkyl Halides
7.1 Introduction
7.2 The (E )–(Z ) System for Designating Alkene Diastereomers
7.3 Relative Stabilities of Alkenes
7.4 Cycloalkenes
7.5 Synthesis of Alkenes via Elimination Reactions
7.6 Dehydrohalogenation of Alkyl Halides
7.7 Acid-Catalyzed Dehydration of Alcohols
7.8 Carbocation Stability and the Occurrence of olecular Rearrangements
7.9 The Acidity of Terminal Alkynes
7.10 Synthesis of Alkynes by Elimination Reactions
7.11 Terminal Alkynes can be Converted to Nucleophiles for Carbon–Carbon Bond Formation
7.12 Hydrogenation of Alkenes
7.13 Hydrogenation: The Function of the Catalyst
7.14 Hydrogenation of Alkynes
7.15 An Introduction to Organic Synthesis
Chapter 8 Alkenes and Alkynes II: Addition Reactions
8.1 Addition Reactions of Alkenes
8.2 Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov’s Rule
8.3 Stereochemistry of the Ionic Addition to an Alkene
8.4 Addition of Water to Alkenes: Acid-Catalyzed Hydration
8.5 Alcohols from Alkenes through Oxymercuration–Demercuration: Markovnikov Addition
8.6 Alcohols from Alkenes through Hydroboration–Oxidation: Anti-Markovnikov Syn Hydration
8.7 Hydroboration: Synthesis of Alkylboranes
8.8 Oxidation and Hydrolysis of Alkylboranes
8.9 Summary of Alkene Hydration Methods
8.10 Protonolysis of Alkylboranes
8.11 Electrophilic Addition of Bromine and Chlorine to Alkenes
8.12 Stereospecific Reactions
8.13 Halohydrin Formation
8.14 Oxidation of Alkenes: Syn 1,2-Dihydroxylation
8.15 Oxidative Cleavage of Alkenes
8.16 Electrophilic Addition of Bromine and Chlorine to Alkynes
8.17 Addition of Hydrogen Halides to Alkynes
8.18 Oxidative Cleavage of Alkynes
8.19 HOW TO Plan a Synthesis: Some Approaches and Examples
8.20 Dimerization of Alkene
8.21 Prins Reaction
Chapter 9 Radical Reactions
9.1 Introduction: How Radicals Form and How They React
9.2 Homolytic Bond Dissociation Energies (DH °)
9.3 Reactions of Alkanes with Halogens
9.4 Chlorination of Methane: Mechanism of Reaction
9.5 Halogenation of Higher Alkanes
9.6 Reactions That Generate Tetrahedral Chirality Centers
9.7 Allylic Substitution and Allylic Radicals
9.8 Benzylic Substitution and Benzylic Radicals
9.9 Radical Addition to Alkenes: The Anti-Markovnikov Addition of Hydrogen Bromide
9.10 Other Important Radical Reactions
Chapter 10 Alcohols and Ethers
10.1 Structure and Nomenclature
10.2 Physical Properties of Alcohols and Ethers
10.3 Synthesis of Alcohols from Alkenes
10.4 Reactions of Alcohols
10.5 Alcohols as Acids
10.6 Conversion of Alcohols into Alkyl Halides
10.7 Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides
10.8 Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCl2
10.9 Tosylates, Mesylates, and Triflates: Leaving Group Derivatives of Alcohols
10.10 Synthesis of Ethers
10.11 Reactions of Ethers
10.12 Epoxides
10.13 Reactions of Epoxides
10.14 Anti 1,2-Dihydroxylation of Alkenes via Epoxides
10.15 Crown Ethers
Chapter 11 Alcohols from Carbonyl Compounds. Oxidation–Reduction and Organometallic Compounds
11.1 Structure of the Carbonyl Group
11.2 Oxidation–Reduction Reactions in Organic Chemistry
11.3 Alcohols by Reduction of Carbonyl Compounds
11.4 Oxidation of Alcohols
11.5 Organometallic Compounds
11.6 Preparation of Organolithium and Organomagnesium Compounds
11.7 Reactions of Organolithium and Organomagnesium Compounds
11.8 Alcohols from Grignard Reagents
11.9 Lithium Dialkylcuprates: The Corey–Posner, Whitesides– House Synthesis
Chapter 12 Conjugated Unsaturated Systems
12.1 Introduction
12.2 Alkadienes and Polyunsaturated Hydrocarbons
12.3 1,3-Butadiene: Electron Delocalization
12.4 Electrophilic Attack on Conjugated Dienes: 1,4-Addition
12.5 The Diels–Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes
Chapter 13 Aromatic Compounds
13.1 The Discovery of Benzene
13.2 Nomenclature of Benzene Derivatives
13.3 Reactions of Benzene
13.4 The Kekulé Structure for Benzene
13.5 The Thermodynamic Stability of Benzene
13.6 Modern Theories of the Structure of Benzene
13.7 Hückel’s Rule: The (4n + 2)p Electron Rule
13.8 Other Aromatic Compounds
13.9 Heterocyclic Aromatic Compounds
Chapter 14 Reactions of Aromatic Compounds
14.1 Electrophilic Aromatic Substitution Reactions
14.2 A General Mechanism for Electrophilic Aromatic Substitution
14.3 Halogenation of Benzene
14.4 Nitration of Benzene
14.5 Sulfonation of Benzene
14.6 Friedel–Crafts Alkylation
14.7 Friedel–Crafts Acylation
14.8 Limitations of Friedel–Crafts Reactions
14.9 Synthetic Applications of Friedel–Crafts Acylations: The Clemmensen and Wolff–Kishner Reductions
14.10 Substituents Can Affect Both the Reactivity of the Ring and the Orientation of the Incoming Group
14.11 How Substituents Affect Electrophilic Aromatic Substitution: A Closer Look
14.12 Reactions of the Side Chain of Alkylbenzenes
14.13 Alkenylbenzenes
14.14 Synthetic Applications
14.15 Allylic and Benzylic Halides in Nucleophilic Substitution Reactions
14.16 Reduction of Aromatic Compounds
Chapter 15 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group
15.1 Introduction
15.2 Nomenclature of Aldehydes and Ketones
15.3 Physical Properties
15.4 Synthesis of Aldehydes
15.5 Synthesis of Ketones
15.6 Nucleophilic Addition to the Carbon–Oxygen Double Bond
15.7 The Addition of Alcohols: Hemiacetals and Acetals
15.8 The Addition of Primary and Secondary Amines
15.9 The Addition of Hydrogen Cyanide: Cyanohydrins
15.10 The Addition of Ylides: The Wittig Reaction
15.11 Oxidation of Aldehydes
15.12 The Baeyer–Villiger Oxidation
15.13 Chemical Analyses for Aldehydes and Ketones
Chapter 16 Aldehydes and Ketones II. Aldol Reactions
16.1 The Acidity of the ` Hydrogens of Carbonyl Compounds: Enolate Anions
16.2 Keto and Enol Tautomers
16.3 Reactions via Enols and Enolates
16.4 Aldol Reactions: Addition of Enolates and Enols to Aldehydes and Ketones
16.5 Crossed Aldol Condensations
16.6 Cyclizations via Aldol Condensation
16.7 Lithium Enolates
Chapter 17 Carboxylic Acids and Their Derivatives. Nucleophilic Addition – Elimination at the Acyl Carbon
17.1 Introduction
17.2 Nomenclature and Physical Properties
17.3 Preparation of Carboxylic Acids
17.4 Acyl Substitution: Nucleophilic Addition– Elimination at the Acyl Carbon
17.5 Acyl Chlorides
17.6 Carboxylic Acid Anhydrides
17.7 Esters
17.8 Amides
17.9 Derivatives of Carbonic Acid
17.10 Decarboxylation of Carboxylic Acids
17.11 Chemical Tests for Acyl Compounds
17.12 Summary of the Reactions of Carboxylic Acids and Their Derivatives
Chapter 18 Amines
18.1 Nomenclature
18.2 Physical Properties and Structure of Amines
18.3 Basicity of Amines: Amine Salts
18.4 Preparation of Amines
18.5 Reactions of Amines
18.6 Reactions of Amines with Nitrous Acid
18.7 Replacement Reactions of Arenediazonium Salts
18.8 Coupling Reactions of Arenediazonium Salts
18.9 Reactions of Amines with Sulfonyl Chlorides
18.10 Synthesis of Sulfa Drugs
18.11 Eliminations Involving Ammonium Compounds
18.12 The Cope Elimination
18.13 Summary of Preparations and Reactions of Amines
Chapter 19 Phenols and Aryl Halides: Nucleophilic Aromatic Substitution
19.1 Structure and Nomenclature of Phenols
19.2 Naturally Occurring Phenols
19.3 Physical Properties of Phenols
19.4 Synthesis of Phenols
19.5 Reactions of Phenols as Acids
19.6 Other Reactions of the O—H Group of Phenols
19.7 Cleavage of Alkyl Aryl Ethers
19.8 Reactions of the Benzene Ring of Phenols
19.9 The Claisen Rearrangement
19.10 Quinones
19.11 Aryl Halides and Nucleophilic Aromatic Substitution
Chapter 20 Carbohydrates
20.1 Introduction
20.2 Monosaccharides
20.3 Mutarotation
20.4 Glycoside Formation
20.5 Other Reactions of Monosaccharides
20.6 Oxidation Reactions of Monosaccharides
20.7 Reduction of Monosaccharides: Alditols
20.8 Reactions of Monosaccharides with henylhydrazine: Osazones
20.9 Synthesis and Degradation of Monosaccharides
20.10 The d Family of Aldoses
20.11 Fischer’s Proof of the Configuration of d-(+)-Glucose
20.12 Disaccharides
20.13 Polysaccharides
20.14 Other Biologically Important Sugars
20.15 Sugars that Contain Nitrogen
20.16 Carbohydrate Antibiotics
Chapter 21 Amino Acids and Proteins
21.1 Introduction
21.2 Amino Acids
21.3 Synthesis of `-Amino Acids
21.4 Polypeptides and Proteins
21.5 Primary Structure of Polypeptides and Proteins
21.6 Secondary, Tertiary, and Quaternary Structures of Proteins
Chapter 22 Carbene and Carbenoids
22.1 Introduction
22.2 Existence of Carbenes
22.3 Formation of Carbenes
22.4 Types of Carbenes
22.5 Reactions of Carbenes
22.6 Rearrangement in Carbenes
Chapter 23 Reaction of Nitrene and Electron Deficient Oxygen
23.1 Migration to Electron Deficient Nitrogen
23.2 Nitrene Formation
23.3 Hofmann—Curtius— Lossen—Schmidt Group of Rearrangements
23.4 Curtius Reaction
23.5 Schmidt Reaction
23.6 Hofmann-Bromamide Reaction or Hofman Rearrangement
23.7 Beckmann Rearrangement
23.8 Stieglitz Rearrangement
Chapter 24 Polymers
24.1 Some Terms Related to Polymers
24.2 Classification of Polymers
24.3 Types of Polymerization Reactions
24.4 Natural Rubber
24.5 Synthetic Rubbers
24.6 Molecular Mass of Polymers
24.7 Biodegradable Polymers
24.8 Polymers of Commercial Importance
Appendix A: Answers to Selected Problems
Appendix B: Chapterwise Solved JEE (Advanced) Questions
Glossary
Index