| Introduction |
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1 | (4) |
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1 | (1) |
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Conventions Used in This Book |
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2 | (1) |
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2 | (1) |
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3 | (1) |
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3 | (1) |
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4 | (1) |
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PART 1 BRUSHING UP ON IMPORTANT ORGANIC CHEMISTRY I CONCEPTS |
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5 | (70) |
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Chapter 1 Organic Chemistry II: Here We Go Again! |
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7 | (8) |
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Recapping Organic Chemistry I |
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8 | (4) |
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8 | (1) |
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9 | (1) |
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9 | (1) |
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9 | (1) |
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Isomerism and optical activity |
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10 | (2) |
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Looking Ahead to Organic Chemistry II |
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12 | (3) |
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Chapter 2 Remembering How We Do It: Mechanisms |
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15 | (14) |
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Duck -- Here Come the Arrows |
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15 | (2) |
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Coming Around to Curved Arrows |
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17 | (1) |
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Getting Ready for Some Basic Moves |
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18 | (1) |
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18 | (1) |
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18 | (1) |
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19 | (1) |
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Combining the Basic Moves |
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19 | (5) |
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21 | (1) |
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Keys to substitution and elimination mechanisms |
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22 | (2) |
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Revisiting Free-Radical Mechanisms |
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24 | (5) |
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Chapter 3 Alcohols and Ethers: Not Just for Drinking and Sleeping |
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29 | (20) |
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Getting Acquainted with Alcohols |
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30 | (12) |
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Structure and nomenclature of alcohols |
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30 | (2) |
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Physical properties of alcohols |
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32 | (1) |
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Making moonshine: Synthesis of alcohols |
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33 | (5) |
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What will they do besides burn? Reactions of alcohols |
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38 | (4) |
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Introducing Ether (Not the Ether Bunny) |
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42 | (6) |
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Structure and nomenclature of ethers |
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42 | (1) |
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Sleepy time: Physical properties of ethers |
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42 | (1) |
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43 | (2) |
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45 | (3) |
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Summarizing the Spectra of Alcohols and Ethers |
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48 | (1) |
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Chapter 4 Conjugated Unsaturated Systems |
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49 | (14) |
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When You Don't Have Enough: Unsaturated Systems |
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49 | (2) |
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50 | (1) |
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50 | (1) |
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51 | (1) |
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Derealization and Resonance |
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51 | (2) |
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52 | (1) |
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Stability of conjugated unsaturated systems |
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53 | (1) |
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Reactions of Conjugated Unsaturated Systems |
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53 | (8) |
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Put in the second string: Substitution reactions |
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53 | (2) |
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55 | (3) |
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More than a tree: Diels-Alder reactions |
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58 | (3) |
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Passing an Exam with Diels-Adler Questions |
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61 | (2) |
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61 | (1) |
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Identifying the reactants |
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62 | (1) |
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Chapter 5 "Seeing" Molecules: Spectroscopy Revisited |
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63 | (12) |
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Chemical Fingerprints: Infrared Spectroscopy |
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64 | (3) |
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65 | (1) |
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65 | (1) |
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65 | (1) |
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65 | (2) |
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Suntans and Beyond: Ultraviolet and Visible Spectroscopy |
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67 | (1) |
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Not Weight Watchers, Mass Watchers: Mass Spectroscopy |
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68 | (2) |
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68 | (1) |
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69 | (1) |
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No Glowing Here: NMR Spectroscopy |
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70 | (5) |
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71 | (2) |
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73 | (2) |
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PART 2 DISCOVERING AROMATIC (AND NOT SO AROMATIC) COMPOUNDS |
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75 | (42) |
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Chapter 6 Introducing Aromatics |
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77 | (12) |
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Benzene: Where It All Starts |
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77 | (6) |
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Figuring out benzene's structure |
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78 | (1) |
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Understanding benzene's resonance |
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79 | (1) |
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80 | (1) |
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Physical properties of benzene |
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80 | (1) |
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Organic math -- Huckel's Rule |
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81 | (1) |
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82 | (1) |
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Smelly Relatives: The Aromatic Family |
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83 | (2) |
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Nomenclature of the aromatic family |
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83 | (1) |
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83 | (1) |
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Branches of aromatic groups |
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84 | (1) |
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Black Sheep of the Family: Heterocyclic Aromatic Compounds |
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85 | (1) |
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Aromatic nitrogen compounds |
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85 | (1) |
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Aromatic oxygen and sulfur compounds |
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85 | (1) |
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Spectroscopy of Aromatic Compounds |
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86 | (3) |
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86 | (1) |
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86 | (1) |
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87 | (1) |
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87 | (2) |
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Chapter 7 Aromatic Substitution Part I: Attack of the Electrophiles |
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89 | (18) |
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Basics of Electrophilic Substitution Reactions |
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90 | (1) |
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91 | (3) |
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91 | (1) |
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92 | (1) |
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93 | (1) |
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94 | (2) |
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94 | (1) |
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95 | (1) |
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96 | (1) |
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Changing Things: Modifying the Reactivity of an Aromatic |
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97 | (8) |
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Lights, camera, action: Directing |
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98 | (5) |
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Turning it on, turning it off: Activating and deactivating |
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103 | (1) |
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104 | (1) |
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Limitations of Electrophilic Substitution Reactions |
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105 | (2) |
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Chapter 8 Aromatic Substitution Part II: Attack of the Nucleophiles and Other Reactions |
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107 | (10) |
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Coming Back to Nucleophilic Substitution Reactions |
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107 | (1) |
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Mastering the Mechanisms of Nucleophilic Substitution Reactions |
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108 | (2) |
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Losing and Gaining: Mechanisms of Elimination/Addition Reactions |
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110 | (1) |
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110 | (1) |
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The elimination/addition mechanism |
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110 | (1) |
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Synthetic Strategies for Making Aromatic Compounds |
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111 | (2) |
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Briefly Exploring Other Reactions |
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113 | (4) |
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PART 3 CARBONYLS: GOOD ALCOHOLS GONE BAD |
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117 | (94) |
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Chapter 9 Comprehending Carbonyls |
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119 | (14) |
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119 | (4) |
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Considering compounds containing the carbonyl group |
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120 | (3) |
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Getting to know the acidic carbonyl |
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123 | (1) |
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123 | (1) |
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124 | (1) |
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Reactivity of the Carbonyl Group |
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125 | (1) |
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Spectroscopy of Carbonyls |
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126 | (7) |
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126 | (1) |
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Ultraviolet-visible (electronic) spectroscopy |
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127 | (1) |
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Nuclear magnetic resonance (NMR) spectroscopy |
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127 | (2) |
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129 | (4) |
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Chapter 10 Aldehydes and Ketones |
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133 | (22) |
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Meeting Alcohol's Relatives: Structure and Nomenclature |
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133 | (2) |
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Defining Physical Properties of Aldehydes and Ketones |
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135 | (1) |
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Creating Aldehydes and Ketones with Synthesis Reactions |
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136 | (6) |
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136 | (2) |
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138 | (1) |
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139 | (3) |
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Taking Them a Step Further: Reactions of Aldehydes and Ketones |
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142 | (12) |
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Nucleophilic attack of aldehydes and ketones |
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142 | (8) |
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Oxidation of aldehydes and ketones |
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150 | (3) |
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The Baeyer-Villiger reaction |
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153 | (1) |
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Checking Out Spectroscopy Specs |
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154 | (1) |
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Chapter 11 Enols and Enolates |
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155 | (24) |
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Getting to Know Enols and Enolates |
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155 | (3) |
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Enough already: Structure of enols and enolates |
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156 | (1) |
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I thought I saw a tautomer |
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156 | (2) |
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Studying the Synthesis of Enols and Enolates |
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158 | (2) |
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Thinking Through Reactions of Enols and Enolates |
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160 | (19) |
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160 | (2) |
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Aldol reactions and condensations |
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162 | (3) |
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Addition reactions to unsaturated aldehydes and ketones |
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165 | (6) |
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Other enolate-related reactions |
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171 | (1) |
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172 | (7) |
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Chapter 12 Carboxylic Acids and Their Derivatives |
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179 | (32) |
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Seeing the Structure and Nomenclature of Carboxylic Acids and Derivatives |
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180 | (5) |
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180 | (1) |
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180 | (5) |
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Checking Out Some Physical Properties of Carboxylic Acids and Derivatives |
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185 | (1) |
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185 | (1) |
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185 | (1) |
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186 | (1) |
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Considering the Acidity of Carboxylic Acids |
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186 | (2) |
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Determining How Carboxylic Acids and Derivatives Are Synthesized |
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188 | (11) |
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Synthesizing carboxylic acids |
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188 | (4) |
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Developing acyl halides with halogen |
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192 | (1) |
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Removing water to form acid anhydrides |
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192 | (2) |
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Uniting acids and alcohols to make esters |
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194 | (3) |
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Bringing acids and bases together to create amides |
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197 | (2) |
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199 | (9) |
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Generous carboxylic acids |
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200 | (1) |
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Simple acyl halide and anhydride reactions |
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201 | (1) |
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201 | (1) |
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Amide reactions, ester's cousins |
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202 | (2) |
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Other reactions of carboxylic acids and derivatives |
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204 | (4) |
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Taking a Look at Spectroscopy and Chemical Tests |
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208 | (3) |
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Identifying compounds through spectral data |
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208 | (1) |
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208 | (3) |
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PART 4 ADVANCED TOPICS (EVERY STUDENT'S NIGHTMARE) |
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211 | (82) |
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Chapter 13 Amines and Friends |
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213 | (26) |
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Breaking Down the Structure and Nomenclature of Nitrogen Compounds |
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213 | (4) |
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214 | (1) |
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Secondary and tertiary amines |
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215 | (1) |
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Quaternary amines (quaternary ammonium salts) |
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215 | (1) |
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216 | (1) |
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Sizing Up the Physical Properties |
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217 | (1) |
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Understanding the Basicity of Nitrogen Compounds |
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217 | (1) |
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Synthesizing Nitrogen Compounds |
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218 | (6) |
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Nucleophilic substitution reactions |
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218 | (2) |
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220 | (4) |
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Seeing How Nitrogen Compounds React |
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224 | (10) |
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Reactions with nitrous acid |
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224 | (2) |
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226 | (3) |
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Coupling reactions of diazonium salts |
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229 | (2) |
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Reactions with sulfonyl chlorides |
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231 | (1) |
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Exploring elimination reactions |
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231 | (3) |
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Mastering Multistep Synthesis |
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234 | (2) |
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Identifying Nitrogen Compounds with Analysis and Spectroscopy |
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236 | (3) |
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Chapter 14 Metals Muscling In: Organometallics |
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239 | (10) |
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Grignard Reagents: Grin and Bear It |
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239 | (6) |
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Preparation of Grignard reagents |
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240 | (1) |
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Reactions of Grignard reagents |
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240 | (5) |
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245 | (1) |
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Formation of Other Organometallics |
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246 | (1) |
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247 | (2) |
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Chapter 15 More Reactions of Carbonyl Compounds |
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249 | (18) |
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Checking Out the Claisen Condensation and Its Variations |
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250 | (4) |
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Doing the two-step: Claisen condensation |
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250 | (2) |
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Circling around: Dieckmann condensation |
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252 | (1) |
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Doubling Up: Crossed Claisen condensation |
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252 | (1) |
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252 | (2) |
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Exploring Acetoacetic Ester Synthesis |
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254 | (2) |
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Defining Malonic Ester Synthesis |
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256 | (3) |
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Working with Other Active Hydrogen Atoms |
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259 | (1) |
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Reacting with Knoevenagel Condensation |
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260 | (1) |
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Looking at Mannich Reactions |
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261 | (2) |
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Creating Enamines: Stork Enamine Synthesis |
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263 | (2) |
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Putting It All Together with Barbiturates |
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265 | (2) |
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Chapter 16 Living Large: Biomolecules |
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267 | (26) |
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Delving into Carbohydrate Complexities |
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268 | (16) |
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Introducing carbohydrates |
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268 | (4) |
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Examining the many reactions of monosaccharides |
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272 | (4) |
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Synthesizing and degrading monosaccharides |
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276 | (3) |
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Meeting the (D-)aldose family |
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279 | (1) |
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Checking out a few disaccharides |
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280 | (1) |
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Looking at some polysaccharides |
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281 | (2) |
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Discovering nitrogen-containing sugars |
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283 | (1) |
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Lipids: Storing Energy Now So You Can Study Longer Later |
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284 | (2) |
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Pondering the properties of fats |
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284 | (1) |
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Soaping up with saponification |
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285 | (1) |
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Bulking Up on Amino Acids and Proteins |
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286 | (7) |
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287 | (1) |
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Perusing the physical properties of amino acids |
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287 | (1) |
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Studying the synthesis of amino acids |
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288 | (5) |
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PART 5 PULLING IT ALL TOGETHER |
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293 | (26) |
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Chapter 17 Overview of Synthesis Strategies |
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295 | (14) |
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Working with One-Step Synthesis |
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296 | (1) |
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Tackling Multistep Synthesis |
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297 | (1) |
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Practicing Retrosynthetic and Synthetic Analysis |
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297 | (12) |
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298 | (2) |
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300 | (4) |
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304 | (3) |
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307 | (1) |
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307 | (2) |
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Chapter 18 Roadmaps and Predicting Products |
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309 | (10) |
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Preparing with Roadmap Basics |
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309 | (1) |
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Practicing Roadmap Problems |
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310 | (6) |
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310 | (1) |
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310 | (2) |
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312 | (1) |
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312 | (2) |
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314 | (1) |
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314 | (2) |
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316 | (3) |
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319 | (18) |
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Chapter 19 Ten Surefire Ways to Fail Organic Chemistry II |
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321 | (4) |
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Simply Read and Memorize Concepts |
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321 | (1) |
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Don't Bother Working the Homework Problems and Exercises |
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322 | (1) |
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322 | (1) |
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Don't Worry About Falling Behind |
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322 | (1) |
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Don't Bother Learning Reactions |
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323 | (1) |
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If Your Textbook Confuses You, Don't Bother with Additional Resources |
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323 | (1) |
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Don't Bother Reading the
Chapter before Attending Class |
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323 | (1) |
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Attend Class Only When You Feel Like It |
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324 | (1) |
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Don't Bother Taking Notes -- Just Listen (When You Aren't Sleeping or Texting) |
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324 | (1) |
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Don't Bother Asking Questions |
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324 | (1) |
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Chapter 20 More than Ten Ways to Increase Your Score on an Organic Chemistry Exam |
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325 | (6) |
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Don't Cram the Night before a Test |
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326 | (1) |
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Try Doing the Problem Sets and Practice Tests Twice |
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326 | (1) |
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Study the Mistakes You Made on Previous Exams |
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326 | (1) |
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Know Precisely Where, Why, and How the Electrons Are Moving |
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327 | (1) |
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Relax and Get Enough Sleep before the Exam |
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327 | (1) |
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327 | (1) |
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Include Formal Charges in Your Structures When Appropriate |
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328 | (1) |
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Check That You Haven't Lost Any Carbon Atoms |
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328 | (1) |
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Include E/Z, R/S, ds/trans Prefixes in Naming Organic Structures |
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329 | (1) |
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Think of Spectroscopy, Especially NMR, As a Puzzle |
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329 | (1) |
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Make Sure That Each Carbon Atom Has Four Bonds |
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329 | (2) |
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Chapter 21 Ten Simple Rules to Remember |
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331 | (6) |
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331 | (1) |
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Positive Charges Attract Negative Charges |
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332 | (1) |
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Bulky Groups Lead to Steric Hindrance |
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332 | (1) |
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332 | (1) |
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Two Groups Must Be in Contact to React |
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333 | (1) |
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333 | (1) |
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The More Electronegative Atom Gets Its Electrons First |
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333 | (1) |
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If Ifs Not C Or H, Ifs Polar |
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334 | (1) |
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Hydrogen Bonding Occurs When H Is Bonded Directly to N, O, or F |
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334 | (1) |
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Markovnikov's Rule: Them That Has Gets |
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335 | (2) |
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337 | (8) |
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Appendix A Named Reactions |
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339 | (4) |
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Appendix B A Few Great Online Resources |
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343 | (2) |
| Index |
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345 | |
