Ch1b2010_week8_b

Ch1b2010_week8_b - addition of organometallic reagents to...

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Organometallic Reagents: Carbon Nucleophiles organometallic reagents : a carbon is bound to a more electropositive metal, resulting in a polar covalent bond with substantial negative charge on carbon MO considerations:
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How to Make Organometallic Reagents Grignard reagents: Organolithiums:
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Organometallic Reagents are Strong Bases organometallic reagents will react with H 2 O and other acidic protons remember: a base can deprotonate acids with pK a values that are lower than it’s conjugate acid.
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Organometallic Reagents Add to Carbonyls remember, carbonyls are electrophilic on carbon: a general mechanism for organometallic addition to carbonyl:
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Organometallic Reagents Add to Carbonyls
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Unformatted text preview: addition of organometallic reagents to carbonyls form C–C bonds aldehyde + organometallic 2° alcohol 3° alcohol ketone + organometallic generally speaking: Divergent Reactivity in Carbonyl Addition Reactions all carbonyl addition reactions can roughly be divided into two categories: the fate of carbonyl additions depends on both : • the nature of the carbonyl electrophile • the nature of the nucleophile Addition of Organometallics to Esters esters undergo double-addition of organometallic reagents Why Are Ketones More Electrophilic than Esters? can use resonance structures to rationalize reactivity trend: trend in carbonyl electrophilicity:...
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