COMPREHENSIVE ORGANIC REACTIONS IN AQUEOUS MEDIA Second Edition CHAO-JUN LI McGillUniversity,Montreal,Canada TAK-HANG CHAN McGillUniversity,Montreal,Canada HongKongPolytechnicUniversity,China WILEY-INTERSCIENCE AJohnWiley&Sons,Inc.,Publication COMPREHENSIVE ORGANIC REACTIONS IN AQUEOUS MEDIA COMPREHENSIVE ORGANIC REACTIONS IN AQUEOUS MEDIA Second Edition CHAO-JUN LI McGillUniversity,Montreal,Canada TAK-HANG CHAN McGillUniversity,Montreal,Canada HongKongPolytechnicUniversity,China WILEY-INTERSCIENCE AJohnWiley&Sons,Inc.,Publication Copyright©2007byJohnWiley&Sons,Inc.Allrightsreserved. PublishedbyJohnWiley&Sons,Inc.,Hoboken,NewJersey. PublishedsimultaneouslyinCanada. Nopartofthispublicationmaybereproduced,storedinaretrievalsystem,ortransmittedin anyformorbyanymeans,electronic,mechanical,photocopying,recording,scanning,or otherwise,exceptaspermittedunderSection107or108ofthe1976UnitedStatesCopyright Act,withouteitherthepriorwrittenpermissionofthePublisher,orauthorizationthrough paymentoftheappropriateper-copyfeetotheCopyrightClearanceCenter,Inc.,222 RosewoodDrive,Danvers,MA01923,(978)750-8400,fax(978)750-4470,oronthewebat www.copyright.com.RequeststothePublisherforpermissionshouldbeaddressedtothe PermissionsDepartment,JohnWiley&Sons,Inc.,111RiverStreet,Hoboken,NJ07030,(201) 748-6011,fax(201)748-6008,oronlineathttp://www.wiley.com/go/permission. LimitofLiability/DisclaimerofWarranty:Whilethepublisherandauthorhaveusedtheirbest effortsinpreparingthisbook,theymakenorepresentationsorwarrantieswithrespecttothe accuracyorcompletenessofthecontentsofthisbookandspecificallydisclaimanyimplied warrantiesofmerchantabilityorfitnessforaparticularpurpose.Nowarrantymaybecreatedor extendedbysalesrepresentativesorwrittensalesmaterials.Theadviceandstrategiescontained hereinmaynotbesuitableforyoursituation.Youshouldconsultwithaprofessionalwhere appropriate.Neitherthepublishernorauthorshallbeliableforanylossofprofitoranyother commercialdamages,includingbutnotlimitedtospecial,incidental,consequential,orother damages. Forgeneralinformationonourotherproductsandservicesorfortechnicalsupport,please contactourCustomerCareDepartmentwithintheUnitedStatesat(800)762-2974,outsidethe UnitedStatesat(317)572-3993orfax(317)572-4002. Wileyalsopublishesitsbooksinavarietyofelectronicformats.Somecontentthatappearsin printmaynotbeavailableinelectronicformats.FormoreinformationaboutWileyproducts, visitourwebsiteat www.wiley.com. WileyBicentennialLogo:RichardJ.Pacifico LibraryofCongressCataloging-in-PublicationDataisavailable. ISBN:978-0-471-76129-7 PrintedintheUnitedStatesofAmerica 10987654321 Dedicated to theauthors’wives and children CONTENTS PREFACE TOTHE SECOND EDITION xv 1 INTRODUCTION 1 1.1 The Structure and Forms of Water / 3 1.2 Properties of Water / 4 1.3 Solvation / 6 1.4 Hydrophobic Effect / 6 1.5 Salt Effect / 8 1.6 Water Under Extreme Conditions / 9 References / 13 2 ALKANES 15 2.1 Oxygenation of Alkanes / 15 2.2 Halogenation of Alkanes / 20 2.3 Formation of Carbon–Carbon Bonds / 20 2.4 D/H Exchange of Alkanes in Water / 21 References / 22 vii
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