3 An Introduction to Organic Compounds: re,Physical Properties,and Structure 88 The Nomenclature of Alkanes 3.3 INDUSTRIAL How is the Octane Number of Gasoline Determined? PROBLEM-SOLVING STRATEGY 101 14151 The Nomenclature of Alkyl Halides 101 3.7 114 MEDICAL CONNECTION:Drugs Bind to Their Receptors 114 3.10 on Sin Bonds 118 MasteringChemistry e2 for Orpanic Chemistry turic Acid,and Blue Jeans 123 PROBLEM-SOLVING STRATEGY 123 .y Conformers of Cyclohexane 124 e in-de 15 Conformers of Disubstituted Cycloh nexanes 129 on Mo -SOLVING STRATE 13 3.16 .Basics of Model Bulding Building and Rec izing Chiral Mol MEDICAL CO INECTION:How High Cholesterol is Tre ESSENTIAL CONCEPTS 135PROBLEMS 136 PART Electrophilic Addition Reactions,Stereochemistry, TWO and Electron Delocalization 141 TUTORIAL Using Molecular Models 142 4 Isomers:The Arrangement of Atoms in Space 143 41 Cis-Trans Isomers Result from Restricted Rotati CHEMICAL CONNECTION:CiS- -Trans inter conversion in Vision 147 Using the E,2 System to Dis somers 147 for Organic Chemistn centers and Stereocenters 二品 PROBLEM-SOLVING STRATEGY 158 89 easured Enantiomeric Excess 163 Compounds with eactaneoengmgrccenter16d as.Fische PROBLEM-SOLVING STRATEGY 168 4.14 Meso Compounds Have Asymmetric Centers but Are Optically Inactive 169 PROBLEM-SOLVING STRATEGY 173 An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure 88 3.1 Alkyl Groups 92 3.2 The Nomenclature of Alkanes 95 INDUSTRIAL CONNECTION: How is the Octane Number of Gasoline Determined? 98 3.3 The Nomenclature of Cycloalkanes 99 PROBLEM-SOLVING STRATEGY 101 3.4 The Nomenclature of Alkyl Halides 101 3.5 The Nomenclature of Ethers 103 3.6 The Nomenclature of Alcohols 104 3.7 The Nomenclature of Amines 106 CHEMICAL CONNECTION: Bad-Smelling Compounds 109 3.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines 109 3.9 Noncovalent Interactions 110 PROBLEM-SOLVING STRATEGY 114 MEDICAL CONNECTION: Drugs Bind to Their Receptors 114 3.10 The Solubility of Organic Compounds 116 BIOLOGICAL CONNECTION: Cell Membranes 118 3.11 Rotation Occurs about Carbon–Carbon Single Bonds 118 3.12 Some Cycloalkanes Have Angle Strain 122 CHEMICAL CONNECTION: Von Baeyer, Barbituric Acid, and Blue Jeans 123 PROBLEM-SOLVING STRATEGY 123 3.13 Conformers of Cyclohexane 124 3.14 Conformers of Monosubstituted Cyclohexanes 127 CHEMICAL CONNECTION: Starch and Cellulose—Axial and Equatorial 128 3.15 Conformers of Disubstituted Cyclohexanes 129 PROBLEM-SOLVING STRATEGY 130 PROBLEM-SOLVING STRATEGY 132 3.16 Fused Cyclohexane Rings 134 MEDICAL CONNECTION: Cholesterol and Heart Disease 134 MEDICAL CONNECTION: How High Cholesterol is Treated Clinically 135 ESSENTIAL CONCEPTS 135 ■ PROBLEMS 136 PART TWO Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization 141 TUTORIAL Using Molecular Models 142 4 Isomers: The Arrangement of Atoms in Space 143 4.1 Cis–Trans Isomers Result from Restricted Rotation 145 CHEMICAL CONNECTION: Cis-Trans Interconversion in Vision 147 4.2 Using the E,Z System to Distinguish Isomers 147 PROBLEM-SOLVING STRATEGY 150 4.3 A Chiral Object Has a Nonsuperimposable Mirror Image 150 4.4 An Asymmetric Center is a Cause of Chirality in a Molecule 151 4.5 Isomers with One Asymmetric Center 152 4.6 Asymmetric Centers and Stereocenters 153 4.7 How to Draw Enantiomers 153 4.8 Naming Enantiomers by the R,S System 154 PROBLEM-SOLVING STRATEGY 157 PROBLEM-SOLVING STRATEGY 158 4.9 Chiral Compounds Are Optically Active 159 4.10 How Specific Rotation Is Measured 161 4.11 Enantiomeric Excess 163 4.12 Compounds with More than One Asymmetric Center 164 4.13 Stereoisomers of Cyclic Compounds 166 PROBLEM-SOLVING STRATEGY 168 4.14 Meso Compounds Have Asymmetric Centers but Are Optically Inactive 169 PROBLEM-SOLVING STRATEGY 171 Using the E,Z system to name alkenes was moved to Chapter 4, so now it appears immediately after using cis and trans to distinguish alkene stereoisomers. for Organic Chemistry MasteringChemistry tutorials guide you through the toughest topics in chemistry with self-paced tutorials that provide individualized coaching. These assignable, in-depth tutorials are designed to coach you with hints and feedback specific to your individual misconceptions. For additional practice on Interconverting Structural Representations, go to MasteringChemistry where the following tutorials are available: • Interconverting Fischer Projections and Perspective Formulas • Interconverting Perspective Formulas, Fischer Projections, and Skeletal Structures • Interconverting Perspective Formulas, Fischer Projections, and Newman Projections for Organic Chemistry Mastering Chemistry tutorials guide you through the toughest topics in chemistry with self-paced tutorials that provide individualized coaching. These assignable, in-depth tutorials are designed to coach you with hints and feedback specific to your individual misconceptions. For additional practice on Molecular Models, go to MasteringChemistry where the following tutorials are available: • Basics of Model Building • Building and Recognizing Chiral Molecules • Recognizing Chirality in Cyclic Molecules