Re: chapter 6
hodgedb@plu.edu
Mon, 31 Mar 1997 13:47:50 -0800 (PST)
Hi,
The strength of a nucleophile is related to the strength of the
interactions between the nucleophile and its surrounding layer of solvent
molecules. A protic solvent has a hydrogen atom attached to an atom of a
strongly electronegative element therefore , molecules of protic solvents
can form hydrogen bonds. A small nucleophile such as a fluoride ion,
because its charge is more concentrated, is more strongly solvated than a
larger one. Hydrogen bonds to a small atom are stronger than those to a
larger atom. A large ion, because the hydrogen bonds between it and the
solvent are weaker, can shed some of its solvent molecules more easily and
therefore will be more nucleophilic. Here are some relative
nucleophilicities in protic solvents:
SH- > CN- > I- > OH- > N3- > Br- > CH3CO2- > Cl- > F- > H2O
I hope that this helps you out.
Dani
On Fri, 21 Mar 1997 barnetca@plu.edu wrote:
> How do you determine a strong nucleophile in a protic solvent?
>
>