Question

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`

Answer 1

`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