An Interactive Guide to Organic Chemistry

Introduction

How to Use this Book

Some things to Remember while Studying  

 Structural and Electronic Representations    

 Abbreviations and Symbols

Arrows Used in Organic Reactions and Processes

Introduction to Organic Compounds

What is Organic Chemistry?  

Ionic Bonds    

Covalent Bonds          

Polar Covalent Bonds          

Lewis Structures         

How to Draw Lewis Structures 

Favorable Charge Separation  

Expanded Formula     

Condensed Structural Formula           

Bond-line Notation     

Molecular Formula     

Isomerism       

Degree of Unsaturation         

Flow Chart for Determining the Relationship Between Organic

Practice Problems       

Classes of Hydrocarbons        

Atomic Orbitals          

Molecular Orbitals      

Formation of Non-bonding Molecular Orbitals    

Formation of Anti-bonding Molecular Orbitals    

Hybridized Orbitals    

Resonance      

General Rules for Drawing Resonance Structures         

Physical Properties of Alkanes           

Induced Dipole  

Hydrogen Bonding   

Boiling Points and Melting Points      

Solubility        

Solvents        

Practice Problems  

Acid and Bases        

Electron Pushing in Acid/Base Reactions      

Generalization for Acids and Bases         

Structure and Acidity 

Bond Length      

Electronegativity         

Inductive Effects         

Practice Problems       

Alkanes          

Iso Groups

Special Groups

IUPAC Rules for Branched Alkanes 

IUPAC Rules for Cycloalkanes         

IUPAC Rules for Complex Groups    

IUPAC Rules for Bicycloalkanes      

Nomenclature Rules for Bicycoalkanes   

Hints for Converting from Side View to Top View         

Classification of Alkyl Carbons         

IUPAC Rules for Halogens   

IUPAC Rules for Functional Groups 

IUPAC Rules for Ethers 

Common Names  

 IUPAC Names

(Winfield iv)

Winfield, Leyte. An Interactive Guide to Organic Chemistry. Kendall Hunt Publishing, Co., 08/2012. VitalBook file.

The citation provided is a guideline. Please check each citation for accuracy before use.

IUPAC Rules for Amines

 Common Names

IUPAC Names

Classification of Amines Practice Problems

Energy Diagram

Projection Formulas in Acyclic Molecules

Conformations in Acyclic Molecules

Conformations in Cyclic Molecules

Drawing the Chair Conformation

1,3-Diaxial Interactions

Conformation of Disubstituted Cycloalkanes Practice Problems

Introduction to Stereochemistry

Chirality

Enantiomers

Drawing Enantiomers Using Tetrahedral Projection

Drawing Enantiomers Using Fischer Projection

Drawing Enantiomers Using Wedge Projection

Translating the Fischer Projection to Tetrahedral

Translating the Fischer Projection to Wedge Projection

Summary of Enantiomer Properties

Topic 5: Conformations

Topic 6: Stereochemistry

Optical

Absolute Configuration

Cahn-Ingold-Prelog R-S Notational System

Rules for Assigning Substituent Priority

Assigning Absolute Configuration for Other Perspective Formulas

Activity

Diastereomers

Drawing the Fischer Projection from Bond-line Structures90

Drawing the Fischer Projection from the Newman Projection

Meso Compounds    

Practice Problems  

(Winfield v)

Winfield, Leyte. An Interactive Guide to Organic Chemistry. Kendall Hunt Publishing, Co., 08/2012. VitalBook file.

The citation provided is a guideline. Please check each citation for accuracy before use.

 

Introduction to Reaction of Organic Compounds

Rate of Processes and Reactions       

Types of Organic Reactions   

Halogenation of Alkanes          

The Mechanism for Free Radical Halogenation of Alkanes   

Chain Initiation     

Chain Propagation       

Chain Termination   

Alkyl Radicals

Topic 7: Chemical Reactions

Regiochemistry in Free Radical Halogenation: Proton Abstraction

Regiochemistry in Free Radical Halogenation: Halogen        

Reactivity

Practice Problems       

Nucleophilic Substitution       

Review of Acid and Bases    

 Reaction Overview      

The Electrophile         

The Leaving Group    

Reactivity of the Halogen Leaving Group 

Other Leaving Groups        

The Nucleophile         

The SN2 Mechanism: Overview       

The SN2 Reaction: Substrate Reactivity        

The SN2 Reaction: Nucleophiles  

The SN2 Reaction: Solvent Effect     

The SN1 Mechanism: Overview       

The SN1 Mechanism: Substrate Reactivity    

Carbocation Rearrangement

The SN1 Reaction: Nucleophiles       

The SN1 Mechanism: Solvent Effects

Summary of Substitution Mechanisms Characteristics and Competition        

Nucleophilic Substitution I: Alkyl Halides as Electrophiles

Competition in SN2 and SN1 Mechanisms

Steps for Drawing Substitution Products

 (Winfield vi)

Winfield, Leyte. An Interactive Guide to Organic Chemistry. Kendall Hunt Publishing, Co., 08/2012. VitalBook file.

The citation provided is a guideline. Please check each citation for accuracy before use.

Practice Problems       

Review of Electrophiles         

Alcohols as Electrophiles: An Overview       

Alcohols as Electrophiles: Formation of Alkyl Halides          

Preparation of Alkyl Halides Using Hydrogen Halide     

 Preparation of Alkyl Halides Using ZnCl2 Catalyst          

Preparation of Alkyl Halides Using Thionyl Chloride 

Preparation of Alkyl Halides Using Trihalophosphates        

Ethers as Electrophiles

Thiols and Thioethers as Electrophiles           

Epoxides as Electrophiles       

Generating Oxygen Nucleophiles      

Generating Carbon Nucleophiles       

 Practice Problems

Review of Classes of Hydrocarbons  

Nomenclature of Alkenes       

cis/trans or E/Z Notation  

Bonds        

Properties of Alkenes 

Electronic Effects of Alkenes 

Steric Effects    

Oxidation and Reduction in Organic Molecules        

Introduction to Elimination Reactions        

Elimination Reaction: Dehalogenation

Elimination Reaction: Dehydration      

Elimination Reaction: Dehydrohalogenation          

E2 Elimination

Bases Used in the Mechanisms   

Stereochemistry

The Zaitsev Rule        

E2 Mechanism: Hofmann’s Rule         

E1 Mechanism: Overview      

(Winfield vii)

Winfield, Leyte. An Interactive Guide to Organic Chemistry. Kendall Hunt Publishing, Co., 08/2012. VitalBook file.

The citation provided is a guideline. Please check each citation for accuracy before use.

Substitution Versus Elimination         

Practice Problems

Topic 11: Addition Reactions and Oxidations of Alkenes

Summary of Reactions

Electrophilic Addition

Regiochemistry in the Electrophilic Addition Reactions

Stereochemistry in the Electrophilic Addition Reactions

Addition of Hydrogen Halide: Hydrohalogenation

Addition of Sulfuric Acid

Addition of Water: Hydration

Addition of Hydrogen: Hydrogenation

Addition of Halogens: Halogenation

Addition of (Hydroxyalkyl)mercury Compounds      

Addition of Borane Molecules: Hydroboration 11.10 Oxidation of Alkenes

Epoxidation

Overview of Oxidative Cleavage

Formation of Diols

Oxidative Cleavage with KMnO4

Ozonolysis Practice Problems

Structure and Nomenclature

Formation of Alkynes from Acetylide Ions

Formation of Alkynes by Elimination

Overview of Alkyne Addition Reactions

Addition of Hydrogen Halides

Addition of Halogens

Addition of Hydrogen

Metal-Catalyzed Hydrogenation

Lindlar’s Catalyst

Dissolving Metal Reduction

Hydration of Alkynes: Oxymercuration

Hydration of Alkynes: Hydroboration

Oxidation of Alkynes

(Winfield viii)

Winfield, Leyte. An Interactive Guide to Organic Chemistry. Kendall Hunt Publishing, Co., 08/2012. VitalBook file.

The citation provided is a guideline. Please check each citation for accuracy before use.

Practice Problems

Introduction to Resonance and Aromaticity

Conjugation

Bonding in Conjugated Dienes

Topic 13: Conjugated Molecules: Structure, Properties, and Reactivity

Conjugated and Isolated Dienes 14

Cumulated Dienes

Conformations of Dienes

Resonance Stabilization

Electrophilic Addition in Isolated Dienes

Electrophilic Addition in Conjugated Dienes

Reaction Overview

Reaction Mechanism

Thermodynamics Versus Kinetics

Double Bond Reactivity

Diels-Alder Reaction: Overview

Diels-Alder Reaction: Stereochemistry

Diels-Alder Reaction: Substituent Effect

Other Diels-Alder Reactions

Retro Diels-Alder

Intermolecular Diels-Alder Practice Problems

Topic 14: Aromaticity and Reactions of Benzene and Substituted Benzene

Nomenclature

Monosubstituted Benzene

Disubstituted Benzene

Multiple and Complex Substitutents

Annulenes

Fused Aromatic Compounds

Hetero Aromatic Compounds

Aromaticity

Resonance Stabilization

Planarity

Electrons

 

(Winfield ix)

Winfield, Leyte. An Interactive Guide to Organic Chemistry. Kendall Hunt Publishing, Co., 08/2012. VitalBook file.

The citation provided is a guideline. Please check each citation for accuracy before use.

Other Aromatic molecules

Heterocyclic Aromatic Compounds

Reduction and Oxidation Reactions

Birch Reduction

Side Chain Reduction

Side Chain Oxidation

Electrophilic Aromatic Substitution

Halogenation of Benzene

Nitration of Benzene

Sulfonation of Benzene

Friedel-Crafts Alkylation

Friedel-Crafts Acylation

Practice Problems

 (Winfield x)

Winfield, Leyte. An Interactive Guide to Organic Chemistry. Kendall Hunt Publishing, Co., 08/2012. VitalBook file.

The citation provided is a guideline. Please check each citation for accuracy before use.