Which is a better nucleophile?

d. CH₃O⁻ or CH₃OH in DMSO

Rank the following species in each set from best nucleophile to poorest nucleophile.

a.

Rank the following species in each set from best nucleophile to poorest nucleophile.

b.

Rank the reactivity of the following anions with a general electrophile from least to most reactive.

Which nucleophile would be more reactive in the solvent given?

(b)

For each pair, choose the more reactive nucleophile.

(a)

In contrast to the results of Assessment 13.18, when a secondary haloalkane is treated with sodium ethanethiolate, we predict formation of a thioether. How is this rationalized?

Between pyrrole and pyrrolidine, which nitrogen would be most nucleophilic? Why?