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《有机化学》课程教学资源（参考书籍）Organic Chemistry II For Dummies 2010, John T. Moore, EdD Richard H. Langley, PhD

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Contents at a Glance Introduction ................................................................ 1 Part I: Brushing Up on Important Organic Chemistry I Concepts ....................................... 7 Chapter 1: Organic Chemistry II: Here We Go Again! ....................................................9 Chapter 2: Remembering How We Do It: Mechanisms ................................................17 Chapter 3: Alcohols and Ethers: Not Just for Drinking and Sleeping ........................31 Chapter 4: Conjugated Unsaturated Systems...............................................................53 Chapter 5: “Seeing” Molecules: Spectroscopy Revisited ............................................67 Part II: Discovering Aromatic (And Not So Aromatic) Compounds ........................................... 79 Chapter 6: Introducing Aromatics .................................................................................81 Chapter 7: Aromatic Substitution Part I: Attack of the Electrophiles .......................93 Chapter 8: Aromatic Substitution Part II: Attack of the Nucleophiles and Other Reactions ...........................................................................111 Part III: Carbonyls: Good Alcohols Gone Bad ............. 121 Chapter 9: Comprehending Carbonyls ........................................................................123 Chapter 10: Aldehydes and Ketones ...........................................................................137 Chapter 11: Enols and Enolates ...................................................................................161 Chapter 12: Carboxylic Acids and Their Derivatives ................................................187 Part IV: Advanced Topics (Every Student’s Nightmare) .............................................. 219 Chapter 13: Amines and Friends ..................................................................................221 Chapter 14: Metals Muscling In: Organometallics .....................................................249 Chapter 15: More Reactions of Carbonyl Compounds ..............................................261 Chapter 16: Living Large: Biomolecules ......................................................................281 02_178157-ftoc.indd ix 5/28/10 9:44 AM

Table of Contents Introduction ................................................................. 1 About This Book ..............................................................................................1 Conventions Used in This Book .....................................................................2 What You’re Not to Read ................................................................................2 Foolish Assumptions .......................................................................................2 How This Book Is Organized ..........................................................................3 Part I: Brushing Up on Important Organic Chemistry I Concepts ...... 3 Part II: Discovering Aromatic (And Not So Aromatic) Compounds .........................................................................................3 Part III: Carbonyls: Good Alcohols Gone Bad .....................................3 Part IV: Advanced Topics (Every Student’s Nightmare)...................4 Part V: Pulling It All Together ...............................................................4 Part VI: The Part of Tens .......................................................................4 Icons Used in This Book .................................................................................4 Where to Go from Here ...................................................................................5 Part I: Brushing Up on Important Organic Chemistry I Concepts ........................................ 7 Chapter 1: Organic Chemistry II: Here We Go Again! . . . . . . . . . . . . . . .9 Recapping Organic Chemistry I ...................................................................10 Intermolecular forces ..........................................................................10 Functional groups ................................................................................11 Reactions ..............................................................................................11 Spectroscopy ........................................................................................11 Isomerism and optical activity ...........................................................12 Looking Ahead to Organic Chemistry II ......................................................14 Chapter 2: Remembering How We Do It: Mechanisms . . . . . . . . . . . . .17 Duck — Here Come the Arrows ...................................................................17 Coming Around to Curved Arrows ..............................................................19 Getting Ready for Some Basic Moves .........................................................20 Bond → lone pair .................................................................................21 Bond → bond ........................................................................................21 Lone pair → bond ................................................................................22 Combining the Basic Moves .........................................................................22 Intermediates .......................................................................................24 Keys to substitution and elimination mechanisms .........................25 Revisiting Free-Radical Mechanisms ...........................................................27 02_178157-ftoc.indd xi 5/28/10 9:44 AM

xii Organic Chemistry II For Dummies Chapter 3: Alcohols and Ethers: Not Just for Drinking and Sleeping. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .31 Getting Acquainted with Alcohols ...............................................................31 Structure and nomenclature of alcohols ..........................................32 Physical properties of alcohols .........................................................33 Making moonshine: Synthesis of alcohols ........................................34 What will they do besides burn? Reactions of alcohols .................40 Introducing Ether (Not the Ether Bunny) ...................................................46 Structure and nomenclature of ethers ..............................................46 Sleepy time: Physical properties of ethers .......................................46 Synthesis of ethers ..............................................................................47 Reactions of ethers ..............................................................................49 Summarizing the Spectra of Alcohols and Ethers .....................................51 Chapter 4: Conjugated Unsaturated Systems . . . . . . . . . . . . . . . . . . . . .53 When You Don’t Have Enough: Unsaturated Systems ..............................53 Conjugated systems ............................................................................53 The allylic radical ................................................................................54 Butadiene ..............................................................................................55 Delocalization and Resonance .....................................................................56 Resonance rules ...................................................................................56 Stability of conjugated unsaturated systems ...................................57 Reactions of Conjugated Unsaturated Systems .........................................57 Put in the second string: Substitution reactions .............................57 Electrophilic addition ..........................................................................59 More than a tree: Diels-Alder reactions ............................................62 Passing an Exam with Diels-Adler Questions .............................................65 Indentifying the product .....................................................................65 Identifying the reactants .....................................................................66 Chapter 5: “Seeing” Molecules: Spectroscopy Revisited . . . . . . . . . .67 Chemical Fingerprints: Infrared Spectroscopy ..........................................68 Double bonds .......................................................................................68 Triple bonds .........................................................................................69 O-H and N-H stretches .........................................................................69 C-H stretches ........................................................................................69 Suntans and Beyond: Ultraviolet and Visible Spectroscopy ....................70 Not Weight Watchers, Mass Watchers: Mass Spectroscopy ...................72 The molecular ion ................................................................................72 Fragmentation ......................................................................................73 No Glowing Here: NMR Spectroscopy .........................................................73 Proton ....................................................................................................74 Carbon-13 ..............................................................................................77 02_178157-ftoc.indd xii 5/28/10 9:44 AM

Table of Contents xiii Part II: Discovering Aromatic (And Not So Aromatic) Compounds ............................................ 79 Chapter 6: Introducing Aromatics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .81 Benzene: Where It All Starts .........................................................................81 Figuring out benzene’s structure .......................................................81 Understanding benzene’s resonance ................................................83 The stability of benzene ......................................................................84 Physical properties of benzene ..........................................................85 Organic math — Hückel’s Rule ..........................................................85 Other aromatics ...................................................................................87 Smelly Relatives: The Aromatic Family ......................................................87 Nomenclature of the aromatic family................................................87 Derivatives of benzene ........................................................................88 Branches of aromatic groups .............................................................89 Black Sheep of the Family: Heterocyclic Aromatic Compounds .............89 Aromatic nitrogen compounds ..........................................................90 Aromatic oxygen and sulfur compounds ..........................................90 Spectroscopy of Aromatic Compounds ......................................................90 IR ............................................................................................................91 UV-vis.....................................................................................................91 NMR .......................................................................................................91 Mass spec..............................................................................................92 Chapter 7: Aromatic Substitution Part I: Attack of the Electrophiles. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .93 Basics of Electrophilic Substitution Reactions ..........................................94 Reactions of Benzene ....................................................................................95 Halogenation of benzene.....................................................................95 Nitration of benzene ............................................................................96 Sulfonation of benzene ........................................................................97 Friedel-Crafts Reactions ................................................................................99 Alkylation ..............................................................................................99 Acylation .............................................................................................100 Why Do an Alkylation? ................................................................................101 Changing Things: Modifying the Reactivity of an Aromatic ...................101 Lights, camera, action: Directing .....................................................102 Turning it on, turning it off: Activating and deactivating .............107 Steric hindrance .................................................................................109 Limitations of Electrophilic Substitution Reactions ...............................109 02_178157-ftoc.indd xiii 5/28/10 9:44 AM

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