Contents 2.6 Cis,Trans Isomerism in Cycloalkanes and Bicycloalkanes 91 HOW TO Convert Planar Cyclohexanes to Chair Cyclohexanes 93 MCAT PRACTICE:PASSAGE AND QUESTIONS Tetrodotoxin 98 2.7 Physical Properties of Alkanes and Cycloalkanes99 2.8 Reactions of Alkanes 102 2.9 Sources and Importance of Alkanes 104 CHEMICAL CONNECTIONS Octane Rating:What Those Numbers at the Pump Mean 106 Summary 107.Problems 109 3 Stereoisomerism and Chirality 117 3.1 Chirality-The Handedness of Molecules 118 3.2 Stereoisomerism 119 HOWTO Draw Chiral Molecules 120 3.3 Naming Chiral Centers-The R,S System 124 HOW TO Assign R or S Configuration to a Chiral Center 126 3.4 Acyclic Molecules with Two or More Stereocenters 127 HOWTO Quickly Draw and Recognize Enantiomers and Diastereomers 133 3.5 Cyclic Molecules with Two or More Chiral Centers 133 3.6 Tying All the Terminology Together 136 3.7 Optical Activity-How Chirality Is Detected in the Laboratory 138 3.8 The Significance of Chirality in the Biological World 142 CONNECTIONS TO BIOLOGICAL CHEMISTRY Chiral Drugs 143 MCAT PRACTICE:PASSAGE AND QUESTIONS Amino Acid Stereochemistry 144 3.9 Separation of Enantiomers-Resolution 145 Summary 148.Problems 151 4 Acids and Bases 157 4.1 Arrhenius Acids and Bases 157 4.2 Bronsted-Lowry Acids and Bases 158 4.3 Acid Dissociation Constants,pK,and the Relative Strengths of Acids and Bases 164 4.4 The Position of Equilibrium in Acid-Base Reactions 166 HOWTO Calculate the Constants for Acid-Base Reactions 167 CONNECTIONS TO BIOLOGICAL CHEMISTRY The lonization of unctional Groups at Physiological pH 168 4.5 Thermochemistry and Mechanisms of Acid-Base Reactions 169 4.6 Molecular Structure and Acidity 173 MCAT PRACTICE:PASSAGE AND QUESTIONS Acid-Base Equilibria 178 4.7 Lewis Acids and Bases 179 Summary 181 Problems 184 Unless otherwise noted all art on this pageCengage Learning 2013 Unless otherwise noted all art on this page © Cengage Learning 2013 Contents viii 2.6 Cis,Trans Isomerism in Cycloalkanes and Bicycloalkanes 91 HoW To Convert Planar Cyclohexanes to Chair Cyclohexanes 93 MCAT PrACTICE: PASSAgE And QuESTIonS Tetrodotoxin 98 2.7 Physical Properties of Alkanes and Cycloalkanes 99 2.8 Reactions of Alkanes 102 2.9 Sources and Importance of Alkanes 104 CHEMICAL ConnECTIonS Octane Rating: What Those Numbers at the Pump Mean 106 Summary  107 • Problems  109 3 Stereoisomerism and Chirality 117 3.1 Chirality—The Handedness of Molecules 118 3.2 Stereoisomerism 119 HoW To Draw Chiral Molecules 120 3.3 Naming Chiral Centers—The R,S System 124 HoW To Assign R or S Configuration to a Chiral Center 126 3.4 Acyclic Molecules with Two or More Stereocenters 127 HoW To Quickly Draw and Recognize Enantiomers and Diastereomers 133 3.5 Cyclic Molecules with Two or More Chiral Centers 133 3.6 Tying All the Terminology Together 136 3.7 Optical Activity—How Chirality Is Detected in the Laboratory 138 3.8 The Significance of Chirality in the Biological World 142 ConnECTIonS To BIoLogICAL CHEMISTry Chiral Drugs 143 MCAT PrACTICE: PASSAgE And QuESTIonS Amino Acid Stereochemistry 144 3.9 Separation of Enantiomers—Resolution 145 Summary  148 • Problems  151 4 Acids and Bases 157 4.1 Arrhenius Acids and Bases 157 4.2 Brønsted-Lowry Acids and Bases 158 4.3 Acid Dissociation Constants, pKa, and the Relative Strengths of Acids and Bases 164 4.4 The Position of Equilibrium in Acid-Base Reactions 166 HoW To Calculate the Equilibrium Constants for Acid-Base Reactions 167 ConnECTIonS To BIoLogICAL CHEMISTry The Ionization of Functional Groups at Physiological pH 168 4.5 Thermochemistry and Mechanisms of Acid-Base Reactions 169 4.6 Molecular Structure and Acidity 173 MCAT PrACTICE: PASSAgE And QuESTIonS Acid-Base Equilibria 178 4.7 Lewis Acids and Bases 179 Summary  181 • Problems  184 Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it