How would these be classified: as strong/weak nucleophiles or strong/weak bases?

#CH_3SNa#
#NaI#
#CH_2ONa#
#CH_3Br#
#(CH_3)_3CONa#
#CH_3OH#

1 Answer
Mar 28, 2016

#CH_3SNa => #strong nucleophile, weak base
#NaI =># strong nucleophile, weak base
#CH_2ONa=># strong nucleophile, strong base
#CH_3Br =># weak nucleophile, weak base
#(CH_3)_3CONa =># weak nucleophile, weak base
#CH_3OH =># weak nucleophile, weak base

Explanation:

Use the basic classification method:
Nucleophilicity the measure how good a Nucleophile is governed by the following. The ability to give away an electron and bond:
1) Charge
2) Polarizability
3) Solvent (Protic v.s. Aprotic)
4) Steric Hindrance

Basicity is governed by the ability of an electron rich specie to donate it an electron and form a bond with a hydrogen atom

#CH_3SNa => #strong nucleophile, weak base
#NaI =># strong nucleophile, weak base
#CH_2ONa=># strong nucleophile, strong base
#CH_3Br =># weak nucleophile, weak base
#(CH_3)_3CONa =># weak nucleophile, weak base
#CH_3OH =># weak nucleophile, weak base