Polar Protic solves and Nucleophilicity

[SunChip]

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Polar Protic Solvent and Nucleophilicity:

Can anyone explain to me how the relationship between basicity and nucleophilicity is inverted in a protic solvent?

Thanks in advance.

 

[IntelInside]

Polar Protic Solvent and Nucleophilicity:

Can anyone explain to me how the relationship between basicity and nucleophilicity is inverted in a protic solvent?

Thanks in advance.

anions (nucleophiles) will be stabilized due to H-bonding, inhibiting their ability to function as Nu (reducing their reactivity). Small compact anions are especially well stabilized because the charge isnt as diffused as a large anion. So from this information, the halides reactivity will be, from least reactive to most (in polar protic), F- < Cl- < Br- < I-

 

[SunChip]

Thanks, Intel!