Contents Covalent Bonding and Shapes of Molecules 1 Electronic Structure of Atoms 2 1.2 Lewis Model of Bonding 7 HOW TO Quickly Figure Out Formal Charge 14 HOWTO Draw Lewis Structures from Condensed Structural Formulas 16 1.3 Functional Groups 17 1.4 Bond Angles and Shapes of Molecules 22 15 Polar and Nonpolar Molecules 25 MCAT PRACTICE:PASSAGE AND QUESTIONS Fullerenes 26 1.6 Quantum or Wave Mechanics 27 1.7 A Combined Valence Bond and Molecular Orbital Theory Approach to Covalent Bonding 31 CONNECTIONS TO BIOLOGICAL CHEMISTRY Phosphoesters 38 HOWTO Quickly Recognize the Hybridization and Geometry of Atoms 43 1.8 Resonance 43 HOWTO Draw Curved Arrows and Push Electrons in Creating Contributing Structures 44 1.9 Molecular Orbitals for Delocalized Systems 49 MCAT PRACTICE:PASSAGE AND QUESTIONS VSEPR and Resonance 52 1.10 Bond Lengths and Bond Strengths in Alkanes,Alkenes,and Alkynes 53 Summary54·Problems57 2 Alkanes and Cycloalkanes 65 2.1 The Structure of Alkanes 66 2.2 Constitutional lsomerism in Alkanes 67 2.3 Nomenclature of Alkanes and the IUPAC System 70 2.4 Cycloalkanes 75 2.5 Conformations of Alkanes and Cycloalkanes 78 HOW TO Draw Alternative Chair Conformations of Cyclohexane 89 Unessisotelartnhn3Unless otherwise noted all art on this page © Cengage Learning 2013 vii 1 Covalent Bonding and Shapes of Molecules 1 1.1 Electronic Structure of Atoms 2 1.2 Lewis Model of Bonding 7 HoW To Quickly Figure Out Formal Charge 14 HoW To Draw Lewis Structures from Condensed Structural Formulas 16 1.3 Functional Groups 17 1.4 Bond Angles and Shapes of Molecules 22 1.5 Polar and Nonpolar Molecules 25 MCAT PrACTICE: PASSAgE And QuESTIonS Fullerenes 26 1.6 Quantum or Wave Mechanics 27 1.7 A Combined Valence Bond and Molecular Orbital Theory Approach to Covalent Bonding 31 ConnECTIonS To BIoLogICAL CHEMISTry Phosphoesters 38 HoW To Quickly Recognize the Hybridization and Geometry of Atoms 43 1.8 Resonance 43 HoW To Draw Curved Arrows and Push Electrons in Creating Contributing Structures 44 1.9 Molecular Orbitals for Delocalized Systems 49 MCAT PrACTICE: PASSAgE And QuESTIonS VSEPR and Resonance 52 1.10 Bond Lengths and Bond Strengths in Alkanes, Alkenes, and Alkynes 53 Summary  54 • Problems  57 2 Alkanes and Cycloalkanes 65 2.1 The Structure of Alkanes 66 2.2 Constitutional Isomerism in Alkanes 67 2.3 Nomenclature of Alkanes and the IUPAC System 70 2.4 Cycloalkanes 75 2.5 Conformations of Alkanes and Cycloalkanes 78 HoW To Draw Alternative Chair Conformations of Cyclohexane 89 Contents 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