Table of Contents xiii Part I1:Discovering Aromatic (And Not So Aromatic)Compoundsg 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-Huckel's Rule . .85 8 of the aromatic family.... erivative of be ne. anch oups He vclic Aromatic Compounds "90 Aromatic ox and sulfur pounds. 0 R 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. Reac on of benzene zene 97 00 Acvlation 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 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