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

CH_3SNaCH3SNa
NaINaI
CH_2ONaCH2ONa
CH_3BrCH3Br
(CH_3)_3CONa(CH3)3CONa
CH_3OHCH3OH

1 Answer
Mar 28, 2016

CH_3SNa => CH3SNastrong nucleophile, weak base
NaI =>NaI strong nucleophile, weak base
CH_2ONa=>CH2ONa strong nucleophile, strong base
CH_3Br =>CH3Br weak nucleophile, weak base
(CH_3)_3CONa =>(CH3)3CONa weak nucleophile, weak base
CH_3OH =>CH3OH 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 => CH3SNastrong nucleophile, weak base
NaI =>NaI strong nucleophile, weak base
CH_2ONa=>CH2ONa strong nucleophile, strong base
CH_3Br =>CH3Br weak nucleophile, weak base
(CH_3)_3CONa =>(CH3)3CONa weak nucleophile, weak base
CH_3OH =>CH3OH weak nucleophile, weak base