Solution and Answer Guide: Brown et al., Organic Chemistry © 2023, 9780357451861;
Chapter 1: Covalent Bonding and Shapes of Molecules
Solution and Answer Guide
BROWN ET AL., ORGANIC CHEMISTRY © 2023, 9780357451861;
CHAPTER 1: COVALENT BONDING AND SHAPES OF MOLECULES
TABLE OF CONTENTS
In-Chapter Problems .......................................................................................................... 5
Electron Configurations: Problem 1.1 .................................................................................... 5
The Octet Rule: Problem 1.2 ................................................................................................... 5
Electronegativity: Problem 1.3 ................................................................................................ 6
Types of Bonds: Problem 1.4 .................................................................................................. 6
Bond Polarity: Problem 1.5 ...................................................................................................... 7
Lewis Structures: Problem 1.6 ............................................................................................... 7
Formal Charge: Problem 1.7.................................................................................................... 8
Condensed Structural Formulas I: Problem 1.8 .................................................................. 8
Condensed Structural Formulas II: Problem 1.9 ................................................................. 9
Condensed Structural Formulas III: Problem 1.10 .............................................................. 9
Condensed Structural Formulas IV: Problem 1.11 ............................................................... 9
Condensed Structural Formulas V: Problem 1.12 ............................................................... 9
VSEPR: Problem 1.13................................................................................................................ 10
MCAT Practice Questions: Fullerenes ............................................................................. 10
Molecular Dipoles: Problem 1.14 ........................................................................................... 11
Hybridization and Bonding: Problem 1.15 ............................................................................ 12
Contributing Structures I: Problem 1.16 .............................................................................. 13
Contributing Structures II: Problem 1.17 ............................................................................. 13
Relative Contributions to Resonance: Problem 1.18 ......................................................... 14
Contributing Structures and Hybridization: Problem 1.19 ................................................ 14
MCAT Practice Questions: VSEPR and Resonance ..........................................................15
End-of-Chapter Problems.................................................................................................17
Electronic Structure of Atoms.............................................................................................. 17
Problem 1.20 .............................................................................................................................. 17
Problem 1.21 ............................................................................................................................... 17
Problem 1.22 .............................................................................................................................. 17
1
, Solution and Answer Guide: Brown et al., Organic Chemistry © 2023, 9780357451861;
Chapter 1: Covalent Bonding and Shapes of Molecules
Problem 1.23 .............................................................................................................................. 18
Lewis Structures and Formal Charge .................................................................................. 18
Problem 1.24 .............................................................................................................................. 18
Problem 1.25 .............................................................................................................................. 19
Problem 1.26 .............................................................................................................................. 19
Problem 1.27.............................................................................................................................. 20
Problem 1.28 ............................................................................................................................. 20
Problem 1.29 .............................................................................................................................. 21
Problem 1.30 ..............................................................................................................................24
Problem 1.31 ...............................................................................................................................25
Problem 1.32 ............................................................................................................................. 26
Polarity of Covalent Bonds ................................................................................................... 28
Problem 1.33 ............................................................................................................................. 28
Problem 1.34 ............................................................................................................................. 28
Problem 1.35 ............................................................................................................................. 28
Problem 1.36 ............................................................................................................................. 29
Problem 1.37.............................................................................................................................. 30
Bond Angles and Shapes of Molecules .............................................................................. 30
Problem 1.38 ............................................................................................................................. 30
Problem 1.39 ..............................................................................................................................32
Problem 1.40 ..............................................................................................................................34
Functional Groups .................................................................................................................. 35
Problem 1.41 ...............................................................................................................................35
Problem 1.42 ............................................................................................................................. 36
Problem 1.43 .............................................................................................................................. 37
Problem 1.44 .............................................................................................................................. 37
Problem 1.45 .............................................................................................................................. 37
Problem 1.46 ............................................................................................................................. 38
Problem 1.47.............................................................................................................................. 38
Problem 1.48 .............................................................................................................................. 41
Polar and Nonpolar Molecules ............................................................................................. 43
Problem 1.49 ..............................................................................................................................43
*Problem 1.50 ............................................................................................................................45
2
, Solution and Answer Guide: Brown et al., Organic Chemistry © 2023, 9780357451861;
Chapter 1: Covalent Bonding and Shapes of Molecules
Resonance and Contributing Structures ............................................................................ 45
Problem 1.51 ...............................................................................................................................45
Problem 1.52 ............................................................................................................................. 46
Problem 1.53 .............................................................................................................................. 47
Problem 1.54 ............................................................................................................................. 48
Problem 1.55 ............................................................................................................................. 49
Problem 1.56 ............................................................................................................................. 49
Problem 1.57 Think–Pair–Share ........................................................................................... 50
Valence Bond Theory .............................................................................................................. 51
Problem 1.58 .............................................................................................................................. 51
Problem 1.59 ..............................................................................................................................54
*Problem 1.60 ............................................................................................................................57
Problem 1.61 .............................................................................................................................. 58
Combined MO/VB Theory ...................................................................................................... 59
Problem 1.62 ............................................................................................................................. 59
Problem 1.63 ............................................................................................................................. 60
Problem 1.64 ............................................................................................................................. 60
Problem 1.65 .............................................................................................................................. 61
Additional Problems................................................................................................................ 61
Problem 1.66 .............................................................................................................................. 61
Problem 1.67.............................................................................................................................. 64
Problem 1.68 ............................................................................................................................. 64
Problem 1.69 ............................................................................................................................. 64
Problem 1.70 ............................................................................................................................. 65
Problem 1.71 .............................................................................................................................. 66
Problem 1.72.............................................................................................................................. 66
Problem 1.73...............................................................................................................................67
Problem 1.74...............................................................................................................................67
Problem 1.75...............................................................................................................................67
Looking Ahead......................................................................................................................... 68
Problem 1.76.............................................................................................................................. 68
Problem 1.77 .............................................................................................................................. 69
Problem 1.78 .............................................................................................................................. 71
3
, Solution and Answer Guide: Brown et al., Organic Chemistry © 2023, 9780357451861;
Chapter 1: Covalent Bonding and Shapes of Molecules
Problem 1.79 .............................................................................................................................. 72
Problem 1.80 .............................................................................................................................. 72
Molecular Orbitals .................................................................................................................. 73
Problem 1.81 ............................................................................................................................... 73
Problem 1.82 .............................................................................................................................. 74
Problem 1.83 ..............................................................................................................................75
4