In the oxymercuration-demercuration reaction, this phenomenon accelerates the reaction by stabilizing the mercurinium intermediate which is reduced in subsequent steps. This phenomenon is the most widely-accepted explanation for a higher-than-expected prevalence of the alpha epimeric form of glucose in solution which exemplifies the anomeric effect. The "negative" type of this effect causes an elongation of the C-F bond in the beta-fluoroethyl an
In the oxymercuration-demercuration reaction, this phenomenon accelerates the reaction by stabilizing the mercurinium intermediate which is reduced in subsequent steps. This phenomenon is the most widely-accepted explanation for a higher-than-expected prevalence of the alpha epimeric form of glucose in solution which exemplifies the anomeric effect. The "negative" type of this effect causes an elongation of the C-F bond in the beta-fluoroethyl anion. This interaction is the reason why the addition of alkyl substituents to carbocations [carbo-"cat" "ions"] is accompanied by an increase in stability. For 10 points, name this effect which usually involves the delocalization of bonding carbon-hydrogen sigma-electrons to neighboring nonbonding p-orbitals.