Transcription of CARBANIONS - Southern Illinois University Edwardsville
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CARBANIONS - Southern Illinois University Edwardsville
CARBANIONSC arbanions are units that contain a negative charge on a carbon atom. The negativecharge gives good nucleophilic properties to the unit that can be used in the formation ofnew carbon carbon bonds. CARBANIONS thus act as nucleophiles in substitution reactions, incarbonyl addition and substitution reactions, and in 1,4- addition (Michael) carbanionCarbanions bear many substituents that can affect the structure and reactivity of thecarbanion, and can affect the acidity of a parent C-H precursor. Halogens stabilizecarbanions in the order of Br > Cl > F. A prominent I- repulsion between the F andCarbanionic center causes some destabilization in alpha-fluorinated CARBANIONS . Themagnitude of the destabilization depends on the carbanion structure. The destabiziationmaximizes as the carbanion structure approaces a planar configuration. Thus, fluorinatedcarbanions possess pyramidal structues with high barriers to StructureCarbanions are trivalent with sp3 hybridization.
optically active optically active When the rate of deuterium exchange at a chiral center is not equal to the rate of racemization it shows that an intermediate is involved as an ion pair. Carbanion ion-pairs are show to be present through labeling at a chiral center.
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