Organic Chemistry for NEET and other Medical Entrance Examinations | By M S Chouhan | 2nd Edition | Wiley Publication ( English Medium )

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Organic Chemistry for NEET and other Medical Entrance Examinations | By M S Chouhan | 2nd Edition | Wiley Publication ( English Medium ).

Organic Chemistry for NEET and other Medical Entrance Examinations is an adaptation of the classic book Solomons' Organic Chemistry, which is widely used by the students all over the world. This adapted version provides more concise content that is structured as per the syllabus requirement. It is a definitive text offering for students preparing for NEET-UG, which replaced the All-India Pre-Medical test (AIPMT) for admission to MBBS and dental courses across the country. The book derives advantage from the time-tested content of the original book and offers assessment as per the entrance examination requirement. It aims to enhance the learning experience and focus on the problem-solving skills. The premise is to encourage self-study in students, help develop understanding of the concepts and build an aptitude to apply these to problem solving.

About the Author:-

Mahendra Singh Chouhan (MSC Sir) is a renowned name in the realm of Organic Chemistry. Though a Chemical engineer from Mumbai University.

Contents:- 

Preface to the Original Edition

Preface to the Adapted Version

About the Authors

About the Adapting Author

Organic Chemistry Animations and Quizzes

1 Basic Principles of Organic Chemistry

Part I: Bonding and Molecular Structure

1.1 Life and the Chemistry of Carbon Compounds

1.1A Development of the Science of Organic Chemistry

1.2 Chemical Bonds: The Octet Rule

1.2A Ionic Bonds

1.2B Covalent Bonds and Lewis Structures

1.2C How to Write Lewis Structures

1.3 Isomers: Different Compounds that Have the Same Molecular Formula

1.4 How to Write and Interpret Structural Formulas

1.4A More About Dash Structural Formulas

1.4B Condensed Structural Formulas

1.4C Bond-Line Formulas

1.4D Three-Dimensional Formulas

1.5 Resonance Theory

1.5A The Use of Curved Arrows: How to Write Resonance Structures

1.5B Rules for Writing Resonance Structures

1.5C How Do We Decide When One Resonance Structure Contributes More to the Hybrid Than Another?

1.6 The Structure of Methane and Ethane: sp3 Hybridization

1.6A The Structure of Methane

1.6B The Structure of Ethane

1.7 The Structure of Ethene (Ethylene): sp2 Hybridization

1.7A Restricted Rotation and the Double Bond

1.7B Cis–Trans Isomerism

1.8 The Structure of Ethyne (Acetylene): sp Hybridization

1.8A Bond Lengths of Ethyne, Ethene, and Ethane

1.8B A Summary of Important Concepts

1.9 How to Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model

1.9A Methane

1.9B Ammonia

1.9C Water

1.9D Carbon Dioxide

Part II: Families of Carbon Compounds

1.10 Classification of Organic Compounds

1.10A Acyclic or Open Chain Compounds

1.10B Alicyclic or Closed-Chain or Ring Compounds

1.10C Aromatic Compounds

1.10D Homologous Series

1.11 Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds

1.11A Alkanes

1.11B Alkenes

1.11C Alkynes

1.11D Benzene: A Representative Aromatic Hydrocarbon

1.12 Functional Groups

1.12A Alkyl Groups and the Symbol R

1.12B Phenyl and Benzyl Groups

1.13 Alkyl Halides or Haloalkanes

1.14 Alcohols and Phenols

1.15 Ethers

1.16 Amines

1.17 Aldehydes and Ketones

1.18 Carboxylic Acids, Esters, and Amides

1.18A Carboxylic Acids

1.18B Esters

1.18C Amides

1.19 Nitriles

1.20 Summary of Important Families of Organic Compounds

1.20A Functional Groups in Biologically Important Compounds

1.21 Nomenclature of Organic Compounds

1.21A The IUPAC System of Nomenclature

1.21B IUPAC Nomenclature of Alkanes

1.21C Nomenclature of Organic Compounds having Functional Group(s)

1.21D Nomenclature of Substituted Benzene Compounds

1.22 Polar Covalent Bonds

1.22A Polar and Nonpolar Molecules

1.22B Dipole Moments in Alkenes

1.23 Physical Properties and Molecular Structure

1.23A Ionic Compounds: Ion–Ion Forces

1.23B Intermolecular Forces (van der Waals Forces)

1.23C Boiling Points

1.23D Solubilities

Part III: An Introduction to Organic Reactions and their Mechanisms

1.24 Acid–Base Reactions

1.24A Brønsted–Lowry Acids and Bases

1.24B Lewis Acids and Bases

1.25 How to Use Curved Arrows in Illustrating Reactions

1.26 Heterolysis of Bonds to Carbon: Carbocations and Carbanions

1.26A Electrophiles and Nucleophiles

1.27 Homolytic Fission of Bonds

1.28 Electron Displacement Effects in Organic Compounds

1.28A Inductive Effect

1.28B Resonance Structure and Effect

1.28C Electromeric Effect (E Effect)

1.28D Hyperconjugation

1.29 The Strength of Brønsted–Lowry Acids and Bases: Ka and pKa

1.29A Predicting the Strength of Bases

1.29B How to Predict the Outcome of Acid–Base Reactions

1.30 Relationships between Structure and Acidity

1.30A The Effect of Hybridization

1.30B Inductive Effects

1.31 Acidity: Carboxylic Acids versus Alcohols

1.31A The Effect of Delocalization

1.31B The Inductive Effect

1.31C Summary and a Comparison of Conjugate Acid–Base Strengths

1.31D Inductive Effects of Other Groups

1.32 The Effect of the Solvent on Acidity

1.33 A Mechanism for an Organic Reaction

Solved Examples

Solved Previous Years’ NEET Questions

Additional Objective Questions

Answer Key

Hints and Explanations

2 Isomerism

2.1 Types of Isomerism

2.1A Structural (Constitutional) Isomerism

2.1B Stereoisomerism

2.2 Geometrical Isomerism

2.2A E- and Z-Nomenclature

2.2B Geometrical Isomerism in Cyclic Structures

2.3 Chirality and Stereochemistry

2.3A The Biological Significance of Chirality

2.4 Enantiomers and Chiral Molecules

2.5 Molecules having One Chirality Center are Chiral

2.5A Tetrahedral versus Trigonal Stereogenic Centers

2.6 How to Test for Chirality: Planes of Symmetry

2.6A Plane of Symmetry

2.6B Center of Symmetry

2.6C Axis of Symmetry

2.6D Alternating or Improper Axis of Symmetry (Sn or σ)

2.7 Naming Enantiomers: The R,S-System

2.7A How to Assign (R) and (S) Configurations

2.8 Properties of Enantiomers: Optical Activity

2.8A Plane-Polarized Light

2.8B The Polarimeter

2.8C Specific Rotation

2.8D Racemic Forms

2.9 The Synthesis of Chiral Molecules

2.9A Racemic Mixture

2.9B Stereoselective Syntheses

2.10 Molecules with More than One Chirality Center

2.10A How to Draw Stereoisomers for Molecules having More than One Chirality Center

2.10B Meso Compounds

2.10C How to Name Compounds with More than One Chirality Center

2.11 Fischer Projection Formulas

2.11A How to Draw and Use Fischer Projections

2.12 Stereoisomerism of Cyclic Compounds

2.12A Cyclohexane Derivatives

2.13 Relating Configurations through Reactions in Which No Bonds to the Chirality Center are Broken

2.14 Chiral Molecules that do not Possess a Chirality Center

2.15 Conformational Isomerism

2.15A Conformations

2.15B Sawhorse Projections

2.15C Newman Projections

Solved Examples

Solved Previous Years’ NEET Questions

Additional Objective Questions

Answer Key

Hints and Explanations

3 Purification and Characterization of Organic Compounds

3.1 Methods of Purification of Organic Compounds

3.1A Sublimation

3.1B Crystallization

3.1C Distillation

3.1D Differential Extraction

3.1E Chromatography

3.2 Qualitative Analysis of Organic Compounds

3.2A Preliminary Tests

3.2B Detection of Carbon and Hydrogen

3.2C Detection of Other Elements

3.3 Quantitative Analysis

3.3A Carbon and Hydrogen

3.3B Nitrogen

3.3C Halogens

3.3D Sulphur

3.3E Phosphorus

3.3F Oxygen

3.4 Determination of Empirical Formula of the Organic Compound

Solved Examples

Solved Previous Years’ NEET Questions

Additional Objective Questions

Answer Key

Hints and Explanations

4 Alkanes and Cycloalkanes

4.1 Introduction to Alkanes and Cycloalkanes

4.1A Sources of Alkanes: Petroleum

4.2 Shapes of Alkanes

4.3 How to Name Alkanes and Alkyl Groups: The IUPAC System

4.3A How to Name Unbranched Alkyl Groups

4.3B How to Name Branched-Chain Alkanes

4.3C How to Name Branched Alkyl Groups

4.3D How to Classify Hydrogen Atoms

4.4 How to Name Cycloalkanes

4.4A How to Name Monocyclic Cycloalkanes

4.4B How to Name Bicyclic Cycloalkanes

4.5 Physical Properties of Alkanes and Cycloalkanes

4.6 Isomerism

4.7 Synthesis of Alkanes and Cycloalkanes

4.7A Hydrogenation of Alkenes and Alkynes ii

4.7B From Alkyl Halides

4.7C From Carboxylic Acids

4.8 How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency

4.8A Compounds Containing Halogens, Oxygen, or Nitrogen

4.9 Chemical Reactions of Alkanes

4.9A Reactions of Alkanes with Halogens

4.9B Chlorination of Methane: Mechanism of Reaction

4.9C Halogenation of Higher Alkanes

4.9D Other Substitution Reactions

4.9E Combustion of Alkanes

4.9F Controlled (Catalytic) Oxidation

4.9G Isomerization

4.9H Aromatization

4.9I Pyrolysis

4.10 Conformations

4.10A Newman Projections and How to Draw Them

4.10B Conformational Analysis of Ethane

4.10C Conformational Analysis of Butane

4.10D Stereoisomers and Conformational Stereoisomers

4.11 The Relative Stabilities of Cycloalkanes: Ring Strain

4.11A Cyclopropane

4.12 Conformations of Cyclohexane: The Chair and the Boat

4.12A Conformations of Higher Cycloalkanes

4.13 Disubstituted Cycloalkanes: Cis–Trans Isomerism

Solved Examples

Solved Previous Years’ NEET Questions

Additional Objective Questions

Answer Key

Hints and Explanations

5 Alkenes and Alkynes

Part I: Alkenes

5.1 Structure of the Double Bond

5.2 Isomerism

5.3 How to Name Alkenes and Cycloalkenes

5.4 The (E )–(Z ) System for Designating Alkene Diastereomers

5.4A How to Use the (E )–(Z ) System

5.5 Relative Stabilities of Alkenes

5.5A Heat of Reaction

5.5B Overall Relative Stabilities of Alkenes

5.6 Cycloalkenes

5.7 Synthesis of Alkenes by Hydrogenation of Alkynes

5.7A Syn Addition of Hydrogen: Synthesis of cis-Alkenes

5.7B Anti Addition of Hydrogen: Synthesis of trans-Alkenes

5.8 Synthesis of Alkenes via Elimination Reactions

5.8A Dehydrohalogenation of Alkyl Halides

5.8B Dehalogenation of Vicinal Dihalides

5.8C Acid-Catalyzed Dehydration of Alcohols

5.9 Carbocation Stability and the Occurrence of Molecular Rearrangements

5.9A Rearrangements During Dehydration of Secondary Alcohols

5.9B Rearrangement After Dehydration of a Primary Alcohol

5.10 Hydrogenation of Alkenes

5.10A Hydrogenation: The Function of the Catalyst

5.11 Addition Reactions of Alkenes

5.11A How to Understand Additions to Alkenes

5.11B Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov’s Rule

5.11C The Anti-Markovnikov Addition of Hydrogen Bromide Radical Addition to Alkenes

5.11D Addition of Water to Alkenes: Acid-Catalyzed Hydration

5.11E Electrophilic Addition of Bromine and Chlorine to Alkenes

5.11F Addition of Sulphuric Acid

5.12 Oxidation of Alkenes: Syn 1,2-Dihydroxylation

5.12A Oxidative Cleavage of Alkenes

5.12B Cleavage with Ozone

Part II: Alkynes

5.13 Structure of the Triple Bond

5.13A Bond Lengths of Ethyne, Ethene and Ethane

5.14 Isomerism

5.15 How to Name Alkynes

5.16 The Acidity of Terminal Alkynes

5.17 Methods of Preparation

5.17A Synthesis of Alkynes by Elimination Reactions

5.17B Synthesis of Higher Alkynes by Carbon–Carbon Bond Formation in Terminal Alkynes

5.17C Other Methods of Preparation

5.18 Chemical Reactivity

5.18A Electrophilic Addition Reactions

5.18B Oxidation of Alkynes

5.18C Polymerization

Part III: Conjugated Unsaturated Systems

5.19 The Stability of the Allyl Radical

5.19A Molecular Orbital Description of the Allyl Radical

5.19B Resonance Description of the Allyl Radical

5.19C Resonance Theory Revisited

5.20 The Allyl Cation

5.21 Alkadienes and Polyunsaturated Hydrocarbons

5.22 1,3-Butadiene: Electron Delocalization

5.22A Bond Lengths of 1,3-Butadiene

5.22B Conformations of 1,3-Butadiene

5.22C Molecular Orbitals of 1,3-Butadiene

5.23 The Stability of Conjugated Dienes

5.24 Allylic Substitution and Allylic Radicals

5.24A Allylic Chlorination (High Temperature)

5.24B Allylic Bromination with N-Bromosuccinimide (Low Concentration of Br2)

5.25 Electrophilic Attack on Conjugated Dienes: 1,4-Addition

5.25A Kinetic Control versus Thermodynamic Control of a Chemical Reaction

5.26 The Diels–Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes

Solved Examples

Solved Previous Years’ NEET Questions

Additional Objective Questions

Answer Key

Hints and Explanations

xxv

6 Aromatic Compounds and their Reactions

6.1 The Discovery of Benzene

6.2 Nomenclature of Benzene Derivatives

6.3 Structure of Benzene

6.3A Reactions of Benzene

6.3B The Kekulé Structure for Benzene

6.4 The Thermodynamic Stability of Benzene

6.5 Modern Theories of the Structure of Benzene

6.5A The Resonance Explanation of the Structure of Benzene

6.5B The Molecular Orbital Explanation of the Structure of Benzene

6.6 Hückel’s Rule: The 4n + 2π Electron Rule

6.6A How to Diagram the Relative Energies of π Molecular Orbitals

in Monocyclic Systems Based on Hückel’s Rule

6.6B The Annulenes

6.6C Aromatic Ions

6.6D Aromatic, Antiaromatic, and Nonaromatic Compounds

6.7 Other Aromatic Compounds

6.7A Benzenoid Aromatic Compounds

6.7B Nonbenzenoid Aromatic Compounds

6.7C Fullerenes

6.7D Heterocyclic Aromatic Compounds

6.7E Aromatic Compounds in Biochemistry

6.8 Preparation of Arenes

6.9 Physical Properties of Arenes

6.10 Electrophilic Aromatic Substitution Reactions

6.11 A General Mechanism for Electrophilic Aromatic Substitution

6.12 Halogenation of Benzene

6.13 Nitration of Benzene

6.14 Sulfonation of Benzene

6.15 Friedel–Crafts Reactions

6.15A Friedel–Crafts Alkylation

6.15B Friedel–Crafts Acylation

6.15C Limitations of Friedel–Crafts Reactions

6.15D Synthetic Applications of Friedel–Crafts Acylations

6.16 Substituents Can Affect Both the Reactivity of the Ring and the Orientation of the Incoming Group

6.16A How Do Substituents Affect Reactivity?

6.16B Ortho–Para-Directing Groups and Meta-Directing Groups

6.16C Electron-Donating and Electron-Withdrawing Substituents

6.16D Groups: Ortho–Para Directors

6.16E Deactivating Groups: Meta Directors

6.16F Halo Substituents: Deactivating Ortho–Para Directors

6.16G Classification of Substituents

6.17 How Substituents Affect Electrophilic Aromatic Substitution: A Closer Look

6.17A Reactivity: The Effect of Electron and Electron-Withdrawing Groups

6.17B Inductive and Resonance Effects: Theory of Orientation

6.17C Meta-Directing Groups

6.17D Ortho–Para-Directing Groups

6.17E Ortho–Para Direction and Reactivity of Alkylbenzenes

6.17F Summary of Substituent Effects on Orientation and Reactivity

6.18 Reactions of the Side Chain of Alkylbenzenes

6.18A Benzylic Radicals and Cations

6.18B Benzylic Halogenation of the Side Chain

6.19 Oxidation Reactions

6.19A Oxidation of the Benzene Ring

6.19B Oxidation of the Side Chain

6.20 Addition Reactions

6.21 Reduction of Aromatic Compounds

6.21A The Birch Reduction

6.22 Synthetic Applications

6.22A Use of Protecting and Blocking Groups

6.22B Orientation in Disubstituted Benzenes

Solved Examples

Solved Previous Years’ NEET Questions

Additional Objective Questions

Answer Key

Hints and Explanations

7 Alkyl and Aryl Halides

7.1 Classification

7.1A Classification Based on Hybridization of Carbon Atom

Part I: Alkyl Halides (Haloalkanes)

7.2 Nomenclature

7.3 Physical Properties of Alkyl Halides

7.3A Melting and Boiling Points

7.3B Density

7.3C Solubility

7.4 Preparation of Alkyl Halides

7.4A From Alcohols

7.4B From Hydrocarbons

7.4C Halogen Exchange

7.5 Nucleophilic Substitution Reactions of Alkyl Halides

7.5A Nucleophiles and Leaving Groups

7.5B Substitution Nucleophilic Bimolecular (SN2)

7.5C Substitution Nucleophilic Unimolecular (SN1)

7.5D Factors Affecting the Rates of SN1 and SN2 Reactions

7.5E Organic Synthesis: Functional Group Transformations Using SN2 Reactions

7.6 Elimination Reactions of Alkyl Halides

7.6A Dehydrohalogenation

7.6B The E2 Reaction

7.6C The E1 Reaction

7.6D How to Determine Whether Substitution or Elimination is Favored

7.7 Overall Summary–Substitution and Elimination Reactions

7.8 Reaction of Alkyl Halides with Metals

7.9 Reduction of Alkyl Halides to Hydrocarbons

7.10 Polyhalogen Compounds

7.10A Dichloromethane (Methylene Chloride CH2Cl2)

7.10B Trichlormethane (Chloroform CHCl3 )

7.10C Triiodomethane (Iodoform CH3l)

7.10D Tetrachloromethane (Carbon Tetrachloride CCl4 )

7.10E Freons xxvii

Part II: Aryl Halides (Haloarenes)

7.11 Nomenclature

7.12 Preparation of Aryl Halides

7.12A By Electrophilic Substitution

7.12B From Diazonium Salts

7.13 Nucleophilic Aromatic Substitution in Aryl Halides

7.13A Nucleophilic Aromatic Substitution by Addition–Elimination: The SNAr Mechanism

7.13B Nucleophilic Aromatic Substitution through an Elimination–Addition Mechanism: Benzyne

7.13C Phenylation

7.14 Electrophilic Aromatic Substitution Reaction

7.15 Reaction with Metals

Solved Examples

Solved Previous Years’ NEET Questions

Additional Objective Questions

Answer Key

Hints and Explanations

8 Alcohols, Phenols and Ethers

8.1 Structure and Classification

8.1A Monohydric, Dihydric, Trihydric or Polyhydric Alcohols and Phenols

8.1B Classification of Ethers

8.2 Structures of Functional Groups

8.2A Alcohols

8.2B Phenols

8.2C Ethers

8.3 Nomenclature

8.3A Nomenclature of Alcohols

8.3B Nomenclature of Phenols

8.3C Nomenclature of Ethers

8.4 Physical Properties

8.4A Physical Properties of Alcohols

8.4B Physical Properties of Phenols

8.4C Physical Properties of Ethers

8.5 Synthesis of Alcohols

8.5A Alcohols from Alkenes

8.5B Alcohols by Reduction of Carbonyl Compounds

8.5C Alcohols from Grignard Reagents

8.5D By Substitution Reactions on Alkyl Halides

8.6 Synthesis of Phenols

8.6A Laboratory Synthesis

8.6B Industrial Syntheses

8.7 Synthesis of Ethers

8.7A Ethers by Intermolecular Dehydration of Alcohols

8.7B The Williamson Ether Synthesis

8.7C Synthesis of Ethers by Alkoxymercuration–Demercuration

8.8 Reactions of Alcohols

8.8A Reactions Involving Cleavage of O—H Bond (Alcohols as Acids)

8.8B Reactions Involving Cleavage of Carbon–Oxygen (C—O) Bond

8.8C Reactions Involving Alcohol Molecule as a Whole

8.8D Oxidation of Alcohols

8.9 Reactions of Phenols as Acids

8.9A Strength of Phenols as Acids

8.9B Distinguishing and Separating Phenols from Alcohols and Carboxylic Acids

8.9C Reactions of the Benzene Ring of Phenols

8.9D Other Reactions of Phenols

8.10 Reactions of Ethers

8.10A Cleavage of Ethers

8.10B Electrophilic Substitution

8.10C The Claisen Rearrangement

8.11 Distinction Between 1°, 2°, 3° Alcohols

8.11A Lucas Test

8.11B Victor Meyer Test

8.11C Iodofo.

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Product Details

SKU / BOOK Code:	Wiley-neet-organ-chemistry(Eng)
Publisher:	Wiley Publication
Author:	By M S Chouhan
Binding Type:	Paperback
No. of Pages:	888
ISBN-10:	9357466495
ISBN-13:	978-9357466493
Edition:	Second Edition
Language:	English Medium
Publish Year:	2024-07
Weight (g):	500
Product Condition:	New
Reading Age:	Above 10 Years
Country of Origin:	India
Genre:	Book
Manufacturer:	As Per Publisher
Importer:	Not Applicable
Packer:	Fulfilled by The Supplier

Product Description

Organic Chemistry for NEET and other Medical Entrance Examinations | By M S Chouhan | 2nd Edition | Wiley Publication ( English Medium ).

Organic Chemistry for NEET and other Medical Entrance Examinations is an adaptation of the classic book Solomons' Organic Chemistry, which is widely used by the students all over the world. This adapted version provides more concise content that is structured as per the syllabus requirement. It is a definitive text offering for students preparing for NEET-UG, which replaced the All-India Pre-Medical test (AIPMT) for admission to MBBS and dental courses across the country. The book derives advantage from the time-tested content of the original book and offers assessment as per the entrance examination requirement. It aims to enhance the learning experience and focus on the problem-solving skills. The premise is to encourage self-study in students, help develop understanding of the concepts and build an aptitude to apply these to problem solving.

About the Author:-

Mahendra Singh Chouhan (MSC Sir) is a renowned name in the realm of Organic Chemistry. Though a Chemical engineer from Mumbai University.

Contents:- 

Preface to the Original Edition

Preface to the Adapted Version

About the Authors

About the Adapting Author

Organic Chemistry Animations and Quizzes

1 Basic Principles of Organic Chemistry

Part I: Bonding and Molecular Structure

1.1 Life and the Chemistry of Carbon Compounds

1.1A Development of the Science of Organic Chemistry

1.2 Chemical Bonds: The Octet Rule

1.2A Ionic Bonds

1.2B Covalent Bonds and Lewis Structures

1.2C How to Write Lewis Structures

1.3 Isomers: Different Compounds that Have the Same Molecular Formula

1.4 How to Write and Interpret Structural Formulas

1.4A More About Dash Structural Formulas

1.4B Condensed Structural Formulas

1.4C Bond-Line Formulas

1.4D Three-Dimensional Formulas

1.5 Resonance Theory

1.5A The Use of Curved Arrows: How to Write Resonance Structures

1.5B Rules for Writing Resonance Structures

1.5C How Do We Decide When One Resonance Structure Contributes More to the Hybrid Than Another?

1.6 The Structure of Methane and Ethane: sp3 Hybridization

1.6A The Structure of Methane

1.6B The Structure of Ethane

1.7 The Structure of Ethene (Ethylene): sp2 Hybridization

1.7A Restricted Rotation and the Double Bond

1.7B Cis–Trans Isomerism

1.8 The Structure of Ethyne (Acetylene): sp Hybridization

1.8A Bond Lengths of Ethyne, Ethene, and Ethane

1.8B A Summary of Important Concepts

1.9 How to Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model

1.9A Methane

1.9B Ammonia

1.9C Water

1.9D Carbon Dioxide

Part II: Families of Carbon Compounds

1.10 Classification of Organic Compounds

1.10A Acyclic or Open Chain Compounds

1.10B Alicyclic or Closed-Chain or Ring Compounds

1.10C Aromatic Compounds

1.10D Homologous Series

1.11 Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds

1.11A Alkanes

1.11B Alkenes

1.11C Alkynes

1.11D Benzene: A Representative Aromatic Hydrocarbon

1.12 Functional Groups

1.12A Alkyl Groups and the Symbol R

1.12B Phenyl and Benzyl Groups

1.13 Alkyl Halides or Haloalkanes

1.14 Alcohols and Phenols

1.15 Ethers

1.16 Amines

1.17 Aldehydes and Ketones

1.18 Carboxylic Acids, Esters, and Amides

1.18A Carboxylic Acids

1.18B Esters

1.18C Amides

1.19 Nitriles

1.20 Summary of Important Families of Organic Compounds

1.20A Functional Groups in Biologically Important Compounds

1.21 Nomenclature of Organic Compounds

1.21A The IUPAC System of Nomenclature

1.21B IUPAC Nomenclature of Alkanes

1.21C Nomenclature of Organic Compounds having Functional Group(s)

1.21D Nomenclature of Substituted Benzene Compounds

1.22 Polar Covalent Bonds

1.22A Polar and Nonpolar Molecules

1.22B Dipole Moments in Alkenes

1.23 Physical Properties and Molecular Structure

1.23A Ionic Compounds: Ion–Ion Forces

1.23B Intermolecular Forces (van der Waals Forces)

1.23C Boiling Points

1.23D Solubilities

Part III: An Introduction to Organic Reactions and their Mechanisms

1.24 Acid–Base Reactions

1.24A Brønsted–Lowry Acids and Bases

1.24B Lewis Acids and Bases

1.25 How to Use Curved Arrows in Illustrating Reactions

1.26 Heterolysis of Bonds to Carbon: Carbocations and Carbanions

1.26A Electrophiles and Nucleophiles

1.27 Homolytic Fission of Bonds

1.28 Electron Displacement Effects in Organic Compounds

1.28A Inductive Effect

1.28B Resonance Structure and Effect

1.28C Electromeric Effect (E Effect)

1.28D Hyperconjugation

1.29 The Strength of Brønsted–Lowry Acids and Bases: Ka and pKa

1.29A Predicting the Strength of Bases

1.29B How to Predict the Outcome of Acid–Base Reactions

1.30 Relationships between Structure and Acidity

1.30A The Effect of Hybridization

1.30B Inductive Effects

1.31 Acidity: Carboxylic Acids versus Alcohols

1.31A The Effect of Delocalization

1.31B The Inductive Effect

1.31C Summary and a Comparison of Conjugate Acid–Base Strengths

1.31D Inductive Effects of Other Groups

1.32 The Effect of the Solvent on Acidity

1.33 A Mechanism for an Organic Reaction

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Answer Key

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2 Isomerism

2.1 Types of Isomerism

2.1A Structural (Constitutional) Isomerism

2.1B Stereoisomerism

2.2 Geometrical Isomerism

2.2A E- and Z-Nomenclature

2.2B Geometrical Isomerism in Cyclic Structures

2.3 Chirality and Stereochemistry

2.3A The Biological Significance of Chirality

2.4 Enantiomers and Chiral Molecules

2.5 Molecules having One Chirality Center are Chiral

2.5A Tetrahedral versus Trigonal Stereogenic Centers

2.6 How to Test for Chirality: Planes of Symmetry

2.6A Plane of Symmetry

2.6B Center of Symmetry

2.6C Axis of Symmetry

2.6D Alternating or Improper Axis of Symmetry (Sn or σ)

2.7 Naming Enantiomers: The R,S-System

2.7A How to Assign (R) and (S) Configurations

2.8 Properties of Enantiomers: Optical Activity

2.8A Plane-Polarized Light

2.8B The Polarimeter

2.8C Specific Rotation

2.8D Racemic Forms

2.9 The Synthesis of Chiral Molecules

2.9A Racemic Mixture

2.9B Stereoselective Syntheses

2.10 Molecules with More than One Chirality Center

2.10A How to Draw Stereoisomers for Molecules having More than One Chirality Center

2.10B Meso Compounds

2.10C How to Name Compounds with More than One Chirality Center

2.11 Fischer Projection Formulas

2.11A How to Draw and Use Fischer Projections

2.12 Stereoisomerism of Cyclic Compounds

2.12A Cyclohexane Derivatives

2.13 Relating Configurations through Reactions in Which No Bonds to the Chirality Center are Broken

2.14 Chiral Molecules that do not Possess a Chirality Center

2.15 Conformational Isomerism

2.15A Conformations

2.15B Sawhorse Projections

2.15C Newman Projections

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3 Purification and Characterization of Organic Compounds

3.1 Methods of Purification of Organic Compounds

3.1A Sublimation

3.1B Crystallization

3.1C Distillation

3.1D Differential Extraction

3.1E Chromatography

3.2 Qualitative Analysis of Organic Compounds

3.2A Preliminary Tests

3.2B Detection of Carbon and Hydrogen

3.2C Detection of Other Elements

3.3 Quantitative Analysis

3.3A Carbon and Hydrogen

3.3B Nitrogen

3.3C Halogens

3.3D Sulphur

3.3E Phosphorus

3.3F Oxygen

3.4 Determination of Empirical Formula of the Organic Compound

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4 Alkanes and Cycloalkanes

4.1 Introduction to Alkanes and Cycloalkanes

4.1A Sources of Alkanes: Petroleum

4.2 Shapes of Alkanes

4.3 How to Name Alkanes and Alkyl Groups: The IUPAC System

4.3A How to Name Unbranched Alkyl Groups

4.3B How to Name Branched-Chain Alkanes

4.3C How to Name Branched Alkyl Groups

4.3D How to Classify Hydrogen Atoms

4.4 How to Name Cycloalkanes

4.4A How to Name Monocyclic Cycloalkanes

4.4B How to Name Bicyclic Cycloalkanes

4.5 Physical Properties of Alkanes and Cycloalkanes

4.6 Isomerism

4.7 Synthesis of Alkanes and Cycloalkanes

4.7A Hydrogenation of Alkenes and Alkynes ii

4.7B From Alkyl Halides

4.7C From Carboxylic Acids

4.8 How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency

4.8A Compounds Containing Halogens, Oxygen, or Nitrogen

4.9 Chemical Reactions of Alkanes

4.9A Reactions of Alkanes with Halogens

4.9B Chlorination of Methane: Mechanism of Reaction

4.9C Halogenation of Higher Alkanes

4.9D Other Substitution Reactions

4.9E Combustion of Alkanes

4.9F Controlled (Catalytic) Oxidation

4.9G Isomerization

4.9H Aromatization

4.9I Pyrolysis

4.10 Conformations

4.10A Newman Projections and How to Draw Them

4.10B Conformational Analysis of Ethane

4.10C Conformational Analysis of Butane

4.10D Stereoisomers and Conformational Stereoisomers

4.11 The Relative Stabilities of Cycloalkanes: Ring Strain

4.11A Cyclopropane

4.12 Conformations of Cyclohexane: The Chair and the Boat

4.12A Conformations of Higher Cycloalkanes

4.13 Disubstituted Cycloalkanes: Cis–Trans Isomerism

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5 Alkenes and Alkynes

Part I: Alkenes

5.1 Structure of the Double Bond

5.2 Isomerism

5.3 How to Name Alkenes and Cycloalkenes

5.4 The (E )–(Z ) System for Designating Alkene Diastereomers

5.4A How to Use the (E )–(Z ) System

5.5 Relative Stabilities of Alkenes

5.5A Heat of Reaction

5.5B Overall Relative Stabilities of Alkenes

5.6 Cycloalkenes

5.7 Synthesis of Alkenes by Hydrogenation of Alkynes

5.7A Syn Addition of Hydrogen: Synthesis of cis-Alkenes

5.7B Anti Addition of Hydrogen: Synthesis of trans-Alkenes

5.8 Synthesis of Alkenes via Elimination Reactions

5.8A Dehydrohalogenation of Alkyl Halides

5.8B Dehalogenation of Vicinal Dihalides

5.8C Acid-Catalyzed Dehydration of Alcohols

5.9 Carbocation Stability and the Occurrence of Molecular Rearrangements

5.9A Rearrangements During Dehydration of Secondary Alcohols

5.9B Rearrangement After Dehydration of a Primary Alcohol

5.10 Hydrogenation of Alkenes

5.10A Hydrogenation: The Function of the Catalyst

5.11 Addition Reactions of Alkenes

5.11A How to Understand Additions to Alkenes

5.11B Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov’s Rule

5.11C The Anti-Markovnikov Addition of Hydrogen Bromide Radical Addition to Alkenes

5.11D Addition of Water to Alkenes: Acid-Catalyzed Hydration

5.11E Electrophilic Addition of Bromine and Chlorine to Alkenes

5.11F Addition of Sulphuric Acid

5.12 Oxidation of Alkenes: Syn 1,2-Dihydroxylation

5.12A Oxidative Cleavage of Alkenes

5.12B Cleavage with Ozone

Part II: Alkynes

5.13 Structure of the Triple Bond

5.13A Bond Lengths of Ethyne, Ethene and Ethane

5.14 Isomerism

5.15 How to Name Alkynes

5.16 The Acidity of Terminal Alkynes

5.17 Methods of Preparation

5.17A Synthesis of Alkynes by Elimination Reactions

5.17B Synthesis of Higher Alkynes by Carbon–Carbon Bond Formation in Terminal Alkynes

5.17C Other Methods of Preparation

5.18 Chemical Reactivity

5.18A Electrophilic Addition Reactions

5.18B Oxidation of Alkynes

5.18C Polymerization

Part III: Conjugated Unsaturated Systems

5.19 The Stability of the Allyl Radical

5.19A Molecular Orbital Description of the Allyl Radical

5.19B Resonance Description of the Allyl Radical

5.19C Resonance Theory Revisited

5.20 The Allyl Cation

5.21 Alkadienes and Polyunsaturated Hydrocarbons

5.22 1,3-Butadiene: Electron Delocalization

5.22A Bond Lengths of 1,3-Butadiene

5.22B Conformations of 1,3-Butadiene

5.22C Molecular Orbitals of 1,3-Butadiene

5.23 The Stability of Conjugated Dienes

5.24 Allylic Substitution and Allylic Radicals

5.24A Allylic Chlorination (High Temperature)

5.24B Allylic Bromination with N-Bromosuccinimide (Low Concentration of Br2)

5.25 Electrophilic Attack on Conjugated Dienes: 1,4-Addition

5.25A Kinetic Control versus Thermodynamic Control of a Chemical Reaction

5.26 The Diels–Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes

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xxv

6 Aromatic Compounds and their Reactions

6.1 The Discovery of Benzene

6.2 Nomenclature of Benzene Derivatives

6.3 Structure of Benzene

6.3A Reactions of Benzene

6.3B The Kekulé Structure for Benzene

6.4 The Thermodynamic Stability of Benzene

6.5 Modern Theories of the Structure of Benzene

6.5A The Resonance Explanation of the Structure of Benzene

6.5B The Molecular Orbital Explanation of the Structure of Benzene

6.6 Hückel’s Rule: The 4n + 2π Electron Rule

6.6A How to Diagram the Relative Energies of π Molecular Orbitals

in Monocyclic Systems Based on Hückel’s Rule

6.6B The Annulenes

6.6C Aromatic Ions

6.6D Aromatic, Antiaromatic, and Nonaromatic Compounds

6.7 Other Aromatic Compounds

6.7A Benzenoid Aromatic Compounds

6.7B Nonbenzenoid Aromatic Compounds

6.7C Fullerenes

6.7D Heterocyclic Aromatic Compounds

6.7E Aromatic Compounds in Biochemistry

6.8 Preparation of Arenes

6.9 Physical Properties of Arenes

6.10 Electrophilic Aromatic Substitution Reactions

6.11 A General Mechanism for Electrophilic Aromatic Substitution

6.12 Halogenation of Benzene

6.13 Nitration of Benzene

6.14 Sulfonation of Benzene

6.15 Friedel–Crafts Reactions

6.15A Friedel–Crafts Alkylation

6.15B Friedel–Crafts Acylation

6.15C Limitations of Friedel–Crafts Reactions

6.15D Synthetic Applications of Friedel–Crafts Acylations

6.16 Substituents Can Affect Both the Reactivity of the Ring and the Orientation of the Incoming Group

6.16A How Do Substituents Affect Reactivity?

6.16B Ortho–Para-Directing Groups and Meta-Directing Groups

6.16C Electron-Donating and Electron-Withdrawing Substituents

6.16D Groups: Ortho–Para Directors

6.16E Deactivating Groups: Meta Directors

6.16F Halo Substituents: Deactivating Ortho–Para Directors

6.16G Classification of Substituents

6.17 How Substituents Affect Electrophilic Aromatic Substitution: A Closer Look

6.17A Reactivity: The Effect of Electron and Electron-Withdrawing Groups

6.17B Inductive and Resonance Effects: Theory of Orientation

6.17C Meta-Directing Groups

6.17D Ortho–Para-Directing Groups

6.17E Ortho–Para Direction and Reactivity of Alkylbenzenes

6.17F Summary of Substituent Effects on Orientation and Reactivity

6.18 Reactions of the Side Chain of Alkylbenzenes

6.18A Benzylic Radicals and Cations

6.18B Benzylic Halogenation of the Side Chain

6.19 Oxidation Reactions

6.19A Oxidation of the Benzene Ring

6.19B Oxidation of the Side Chain

6.20 Addition Reactions

6.21 Reduction of Aromatic Compounds

6.21A The Birch Reduction

6.22 Synthetic Applications

6.22A Use of Protecting and Blocking Groups

6.22B Orientation in Disubstituted Benzenes

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7 Alkyl and Aryl Halides

7.1 Classification

7.1A Classification Based on Hybridization of Carbon Atom

Part I: Alkyl Halides (Haloalkanes)

7.2 Nomenclature

7.3 Physical Properties of Alkyl Halides

7.3A Melting and Boiling Points

7.3B Density

7.3C Solubility

7.4 Preparation of Alkyl Halides

7.4A From Alcohols

7.4B From Hydrocarbons

7.4C Halogen Exchange

7.5 Nucleophilic Substitution Reactions of Alkyl Halides

7.5A Nucleophiles and Leaving Groups

7.5B Substitution Nucleophilic Bimolecular (SN2)

7.5C Substitution Nucleophilic Unimolecular (SN1)

7.5D Factors Affecting the Rates of SN1 and SN2 Reactions

7.5E Organic Synthesis: Functional Group Transformations Using SN2 Reactions

7.6 Elimination Reactions of Alkyl Halides

7.6A Dehydrohalogenation

7.6B The E2 Reaction

7.6C The E1 Reaction

7.6D How to Determine Whether Substitution or Elimination is Favored

7.7 Overall Summary–Substitution and Elimination Reactions

7.8 Reaction of Alkyl Halides with Metals

7.9 Reduction of Alkyl Halides to Hydrocarbons

7.10 Polyhalogen Compounds

7.10A Dichloromethane (Methylene Chloride CH2Cl2)

7.10B Trichlormethane (Chloroform CHCl3 )

7.10C Triiodomethane (Iodoform CH3l)

7.10D Tetrachloromethane (Carbon Tetrachloride CCl4 )

7.10E Freons xxvii

Part II: Aryl Halides (Haloarenes)

7.11 Nomenclature

7.12 Preparation of Aryl Halides

7.12A By Electrophilic Substitution

7.12B From Diazonium Salts

7.13 Nucleophilic Aromatic Substitution in Aryl Halides

7.13A Nucleophilic Aromatic Substitution by Addition–Elimination: The SNAr Mechanism

7.13B Nucleophilic Aromatic Substitution through an Elimination–Addition Mechanism: Benzyne

7.13C Phenylation

7.14 Electrophilic Aromatic Substitution Reaction

7.15 Reaction with Metals

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8 Alcohols, Phenols and Ethers

8.1 Structure and Classification

8.1A Monohydric, Dihydric, Trihydric or Polyhydric Alcohols and Phenols

8.1B Classification of Ethers

8.2 Structures of Functional Groups

8.2A Alcohols

8.2B Phenols

8.2C Ethers

8.3 Nomenclature

8.3A Nomenclature of Alcohols

8.3B Nomenclature of Phenols

8.3C Nomenclature of Ethers

8.4 Physical Properties

8.4A Physical Properties of Alcohols

8.4B Physical Properties of Phenols

8.4C Physical Properties of Ethers

8.5 Synthesis of Alcohols

8.5A Alcohols from Alkenes

8.5B Alcohols by Reduction of Carbonyl Compounds

8.5C Alcohols from Grignard Reagents

8.5D By Substitution Reactions on Alkyl Halides

8.6 Synthesis of Phenols

8.6A Laboratory Synthesis

8.6B Industrial Syntheses

8.7 Synthesis of Ethers

8.7A Ethers by Intermolecular Dehydration of Alcohols

8.7B The Williamson Ether Synthesis

8.7C Synthesis of Ethers by Alkoxymercuration–Demercuration

8.8 Reactions of Alcohols

8.8A Reactions Involving Cleavage of O—H Bond (Alcohols as Acids)

8.8B Reactions Involving Cleavage of Carbon–Oxygen (C—O) Bond

8.8C Reactions Involving Alcohol Molecule as a Whole

8.8D Oxidation of Alcohols

8.9 Reactions of Phenols as Acids

8.9A Strength of Phenols as Acids

8.9B Distinguishing and Separating Phenols from Alcohols and Carboxylic Acids

8.9C Reactions of the Benzene Ring of Phenols

8.9D Other Reactions of Phenols

8.10 Reactions of Ethers

8.10A Cleavage of Ethers

8.10B Electrophilic Substitution

8.10C The Claisen Rearrangement

8.11 Distinction Between 1°, 2°, 3° Alcohols

8.11A Lucas Test

8.11B Victor Meyer Test

8.11C Iodofo.

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