Chapter 7, Problem 7.50P

Rank the species in each group in order of increasing nucleophilicity.

a. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{S}}^{-}$, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{O}}^{-}$, ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}{}^{-}$ in ${\text{CH}}_{\text{3}}\text{OH}$

b. ${\text{CH}}_{\text{3}}{\text{NH}}_{\text{2}}$, ${\text{CH}}_{\text{3}}\text{SH}$, ${\text{CH}}_{\text{3}}\text{OH}$.

c. ${}^{-}\text{OH},{\text{F}}^{-},{\text{Cl}}^{-}$ in acetone

d. ${\text{HS}}^{-},{\text{F}}^{-},{\text{Cl}}^{-}$ in ${\text{CH}}_{\text{3}}\text{OH}$