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The first one is pretty straight forward This is one of those cases where carbon is more electronegative as the other element Lithium is actually less electronegative so there is a negative charge on the carbon atom. I.E. carbanion. |dw:1458501302299:dw| this negative charge is highly unstable, because look. it's going to act more as a base rather than a nucleophile because the nearby alkyl groups are donating electron density to the carbon. In-fact this is like one of the strongest bases possible and it's going to aggressively pull a proton off anywhere it can. best target is the hydrogen bonded to the nitrogen atom. |dw:1458501498936:dw|
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