lecture 15.1 - Organic Chemistry William H Brown...

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15- 15-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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15- 15-2 Organometallic Organometallic Compounds Compounds Chapter 15 Chapter 15
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15- 15-3 Organometallic Compounds Organometallic 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 24
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15- 15-4 Grignard Reagents Grignard 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 THF Mg + 1-Bromobutane Butylmagnesium bromide (an alkyl Grignard reagent) ether Br MgBr + ether Mg Br MgBr Bromobenzene Phenylmagnesium bromide (an aryl Grignard reagent)
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15- 15-5 RMgX and RLi RMgX and RLi Grignard reagents dissolve as coordination compounds solvated by ether ethylmagnesium bromide, EtMgBr
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15- 15-6 RMgX and RLi RMgX and RLi Organolithium reagents prepared by reaction of an alkyl, aryl, or alkenyl halide with lithium metal Cl + + 1-Chlorobutane   Butyllithium pentane 2 Li LiCl Li
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15- 15-7 RMgX and RLi RMgX and RLi The carbon-metal bonds in RMgX and RLi are polar covalent 2.5 - 1.2 = 1.3 2.5 - 1.0 = 1.5 2.5 - 1.5 = 1.0 2.5 - 1.6 = 0.9 2.5 - 1.8 = 0.7 2.5 - 1.9 = 0.6 Difference in
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