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Ch_322b_12.06 - Organometallic Compounds Organometallic...

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Organometallic Compounds Organometallic compounds are characterized by the presence of a carbon-metal bond that is polarized as shown: C M !" ! + Note the polarization due to the electronegativity differences. The carbon has carbanion characte r. The degree of charge separation (polar character) in the carbon-metal bond depends on the metal, the structure around carbon, and the solvent. C: M - + ionic bond (Na + , K + ) C M !" ! + polar covalent (Mg, Li) C M !" ! + mostly covalent (Pb, Sn, Hg)
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Reactivity of Organometallics The reactivity of organometallic reagents parallels the degree of ionic character in the carbon-metal bond. Alkylsodium and alkylpotassium reagents are very powerful bases that react explosively with water. Organomercury and organolead compounds are much more stable. Organolithium and organomagnesium halides are reactive, but are reasonably easy to handle, and find wide use in organic synthesis. All organometallics tend to be highly poisonous and harmful.
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