Contents:

ch1 Atomic and Molecular Structure 1

Nomenclature 1 Introduction: The Basic System for Naming Simple Organic Compounds: Alkanes, Cycloalkanes, Haloalkanes, Nitroalkanes, and Ethers 54

ch2 Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties 76

ch3 Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals 128

Nomenclature2 Naming Alkenes, Alkynes, and Benzene Derivatives
163

ch4 Isomerism 1: Conformational and Constitutional Isomers 176

ch5 Isomerism 2: Chirality, Enantiomers, and Diastereomers 224

Nomenclature 3 Considerations of Stereochemistry: R and S configurations about Tetrahedral Stereocenters and Z and E Configurations about Double Bonds 276

ch6 The Proton Transfer Reaction: An Introduction to Mechanisms, Thermodynamics, and Charge Stability 295

ch7 An Overview of the Most Common Elementary Steps 351

Interchapter 1 Molecular Orbitl Theory and Chemical Reactions
388

Nomenclature 4 Naming Compounds with Common Functional Groups: Alcohols, Amines,Ketones, Aldehydes, Carboxylic Acids, Acid Halides, Acid Anhydrides, Nitriles, and Esters 398

ch8 An Introduction to Multistep Mechanisms: SN1 and E1 Reactions 420

ch9 Nucleophilic Substitution and Elimination Reactions 1: Competition among SN2, SN1, E2, and E1 Reactions 466

ch10 Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis 524

ch11 Electrophilic Addition to Nonpolar π Bonds 1: Addition of a Bronsted Acid 570

ch12 Electrophilic Addition to Nonpolar π Bonds 2: Reactions Involving Cyclic Transition States 610

ch13 Organic Synthesis 1: Beginning Concepts 645

ch14 Orbital Interactions 2: Extended π Systems, Conjugation, and Aromaticity 676

ch15 Structure Determination 1:Ultraviolet-Visible and Infrared Spectroscopies 715

ch16 Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry 757

ch17 Nucleophilic Addition to Polar π Bonds 1: Addition of Strong Nucleohiles 815

ch18 Nucleophilic Addition to Polar π Bonds 2: Addition of Weak Nucleohiles and Acid and Base catalysis 861

ch19 Organic Synthesis 2: Intermediate Topics of Synthesis Design, and Useful Reduction and Oxidation Reactions 919

ch20 Nucleophilic addition-Elimination Reactions 1: The General Mechanism Involving Strong Nucleophiles 962

ch21 Nucleophilic Addition-Elimination Reactions 2: Weak Nucleophiles 1006

ch22 Electrophilic Aromatic substitution 1: Substitution on Benzene: useful Accompanying Reactions 1065

ch23 Electrophilic Aromatic Substitution 2: Substitution involving Mono- and Disubstituted Benzene and Other Aromatic Rings 1104

ch24 The Diels-Alder Reaction and Other Pericyclic Reactions 1154

ch25 Reactions Involving Free Radicals 1199

Interchapter 2 Fragmentation Pathways in Mass Spectrometry 1245

ch26 Polymers 1255