Table of Contents

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.

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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.

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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.

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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.

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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.

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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.

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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.