lecture 15.1

lecture 15.1 - 15-15-1Organic Organic H BrownWilliam H...

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Unformatted text preview: 15-15-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson15-15-2OrganometallicOrganometallicCompoundsCompoundsChapter 15Chapter 1515-15-3Organometallic CompoundsOrganometallic Compounds◆Organometallic compound:Organometallic compound:a compound that contains a carbon-metal bond◆In this chapter, we focus on organometallic compounds of Mg, Li, and Cu•these classes illustrate the usefulness of organometallics in modern synthetic organic chemistry•they illustrate how the use of organometallics can bring about transformations that cannot be accomplished in any other way•we discuss several more recent reactions of organometallic compounds in Chapter 2415-15-4Grignard ReagentsGrignard Reagents◆Grignard reagent:Grignard reagent:an organomagnesium compound•prepared by addition of an alkyl, aryl, or alkenyl (vinylic) halide to Mg metal in diethyl ether or THFMg+1-BromobutaneButylmagnesium bromide(an alkyl Grignard reagent)etherBrMgBr+etherMgBrMgBrBromobenzenePhenylmagnesiumbromide(an aryl Grignard reagent)15-15-5RMgX and RLiRMgX and RLi◆Grignard reagents dissolve as coordination compounds solvated by ether•ethylmagnesium bromide, EtMgBr15-15-6RMgX and RLiRMgX and RLi◆Organolithium reagents•prepared by reaction of an alkyl, aryl, or alkenyl halide with lithium metalCl++1-Chlorobutane Butyllithiumpentane2 LiLiClLi15-15-7RMgX and RLiRMgX and RLi◆The carbon-metal bonds in RMgX and RLi are polar covalent2.5 - 1.2 = 1.32.5 - 1.0 = 1.52.5 - 1.5 = 1.02.5 - 1.6 = 0.92.5 - 1.8 = 0.72.5 - 1.9 = 0.6Difference inElectronegativityC-M...
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This note was uploaded on 03/30/2008 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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lecture 15.1 - 15-15-1Organic Organic H BrownWilliam H...

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