0105-Ch15 - Chapter 15 Organometallic Compounds Ch-15 1...

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Chapter 15 Organometallic Compounds Ch-15- 1
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Organometallic Compounds Organometallic compound: Compound with carbon-metal bond: C–M. In this chapter: M = Mg, Li, and Cu. Historically important reagents with continued usefulness for synthetic chemistry. Organometallics can bring about transformations that cannot be accomplished otherwise. Very useful reagents for synthetic chemistry, particularly for C–C-bond formation. More modern reactions with organometallics in Chapter 24. Ch-15- 2
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Grignard Reagents Grignard Reagent: An organomagnesium compound. R–MgX, Ar–MgX, C=C-MgX. Readily available, easily prepared, easy to handle. Ph Br + Mg Et 2 O Ph MgBr Bromobenzene Phenylmagnesium bromide Preparation : Addition of alkyl, aryl, alkenyl (vinylic) halide (X = I, Br; Cl reacts too slowly) to Mg metal in ether (Et 2 O) or THF as solvent. Alkyl Grignard reagents are in equilibrium between monoalkyl and dialkyl magnesium complexes. R MgX 2 R 2 Mg + MgX 2 Ch-15- 3
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Grignard Reagents Grignard reagents (Mg = Lewis acid) dissolve in diethyl ether (Lewis base) as solvated coordination compounds. Ch-15- 4
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Organolithium Reagents Prepared by reaction of an alkyl, aryl, or alkenyl halide with lithium metal. Ch-15- 5 Cl + 2 Li pentane Li + LiCl 1-Chlorobutane Butyl lithium Ð 10 ¡C Like Grignard reagents, organolithium compounds are (1) very reactive nucleophiles, (2) and powerful bases. Organolithium compounds react with atmospheric oxygen and with moisture; must be kept under N 2 or Ar.
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R–MgX and R–Li Carbon–metal bond (R–M): Polar covalent (when the difference in electronegativity is 0.5 to 1.9; see Table 1.16).
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0105-Ch15 - Chapter 15 Organometallic Compounds Ch-15 1...

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