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Unformatted text preview: nucleophiles can act as bases. In either case, these reagents react by donating a pair of electrons to form sigma bonds. Basicity indicates a molecules/atoms ability to accept a proton in an acid-base reaction. Consequently, we can determine the strength of a base by assessing its degree of ionization of water. The basicity for the following are listed in increasing order: I- < Br- < Cl- < R-OH < H2O < -CN < -OH < -OR. Meanwhile, nucleophilicity measures a molecules/atoms ability to cause a substitution reaction (according to Fessenden and Fessenden). The following molecules are listed in order of increasing nucleophilicity: H2O < R-OH < Cl- < Br- < -OH < -OR < I- < -CN. Stronger bases are typically better nucleophiles....
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- Spring '11