xii Organic Chemistry ll For Dummies Chapter 3:Alcohols and Ethers:Not Just for Drinking and Sleeping......................................3 Getting Acquainted with Alcohols. 21 Structure and nomenclature of alcohols. Physical properties of alcohols 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...... .......... Sleepy time:Physical properties of ethers.. ..…46 Synthesis of ethers... 4 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. Resonance rules. ted systems........ ons oconugated Unsarsustitution reactions React onjugat eisecondt tring: than a tree:Die els-Alder reaction with Diels-Adler Questions 65 ldentifying the reactants.. 66 Chapter 5:"Seeing"Molecules:Spectroscopy Revisited..........67 mical Fingerprints:Infrared Spectroscopy.. co and N-H stretches C-H stretche Suntans and Beve nd:Ultraviolet and Visible Spectroscopy. 70 Not Weight Watchers,Mass Watchers:Mass Spectroscopy 79 The molecular ion 72 Fragmentation. 73 No Glowing Here:NMR Spectroscopy. 73 Proton.. .74 Carbon-13.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