Organometallic_compounds - charge which means it is now a...

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Organometallic compounds Organometallic reagents are compounds in which a carbon atom of an organic group is bound to a metal. These species are strong bases and nucleophiles. They are extremely useful in organic synthesis. The most conveniently prepared organometallic compounds are when an haloalkane is reacted with a metal such as Li and Mg. CH 3 Br + 2 Li CH 3 Li + LiBr CH 3 Cl + Mg CH 3 MgCl Organomagnesium compounds are also called Grignard reagents The preparation of alkylmetals from haloalkanes illustrates an important principle in synthetic organic chemistry, the principle of
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Reverse Polarization in which the carbon attached to the halogen is originally + due to the electronegativity of the halogen. This means that the C is an electrophile. Having completed the reaction with the metal the C now has a –
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Unformatted text preview: charge which means it is now a nucleophile. The alkyl group in alkylmetals is strongly basic. This basicity makes organometallic reagents moisture sensitive. In the presence of water, hydrolysis occurs often violently to give a metal hydroxide and an alkane. Organometallic reagents in the synthesis of alcohols When a grignard reagent reacts with methanal (formaldehy) a primary alcohol is formed. When a grignard reacts with any of the other aldehydes in the series a secondary alcohol is formed. The reaction of a ketone such as propanone or acetone also results in the formation of a secondary alcohol. Organometallic reagents react with carbon dioxide to give carboxylic acids....
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