ch 15-1

ch 15-1 - Organometallic Compounds Organometallic compound...

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Organometallic Compounds Organometallic compound: a compound that contains a carbon-metal bond, ex those that contain Mg, Li and Cu organometallics are useful in modern synthetic organic chemistry, affording transformations that would otherwise not be accomplished 1
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Grignard Reagents (RMgX) Grignard reagent: an organomagnesium compound prepared by addition of an alkyl, aryl, or alkenyl (vinylic) halide to Mg metal in diethyl ether or THF (anhydrous solvent) Mg + 1-Bromobutane Butylmagnesium bromide (an alkyl Grignard reagent) ether Br MgBr + ether Mg Br MgBr Bromobenzene Phenylmagnesium bromide (an aryl Grignard reagent) 2
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Organolithium Reagents (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 Which atoms have a partial positive or partial negative charge based on electronegativity differences between C and Cl and C and Li? 3
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Rxns of RMgX and RLi RMgX and RLi are valuable in synthesis as nucleophiles Br  - C Br CH 3 CH 2 CH 2 H H C   - CH 3 CH 2 CH 2 H H Mg 2 + δ + δ - carbon is an electrophile carbon is a nucleophile 4 The addition of RMgBr and RLi reagents to the
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This note was uploaded on 05/26/2008 for the course CHEM 262 taught by Professor Forbes during the Summer '08 term at UNC.

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ch 15-1 - Organometallic Compounds Organometallic compound...

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