What is the periodic trend of halogens in aprotic and protic solutions? Solution

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you go by the phrase "electronegativity reduces nucleophilicity" you will miss every single question comparing halogen nucleophiles in aprotic solvents. F-> Cl- > Br- > I- (in aprotic) Also, who's a better nucleophile?...F- or tert-butoxide? Fluorine of course, despite the fact that it's the most electronegative element my point is: there's a lot that goes into comparing nucleophiles. we can't make blanket statements that "electronegativity decreases nucleophilicity" Exactly. The nucleophilicity of a species can change drastically depending on conditions (e.g. solvent). Note how the question was very clear in pointing out the solvent (protic) - had the solvent been DMSO or acetonitrile, for example, the relative nucleophilicity of Cl- and Br- would have been different.

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