# Nucleophilicity in polar aprotic solvent (DMSO)

The strength of a nucleophile in polar aprotic solvent is proportional to its basicity. Lone pair on O- in the molecules will donate an e- pair to an atom. I'm not sure why the alkene ring in 2 makes it a worse nucleophile compared to 1. Benzene ring is more stable than cyclohexane but the double bond is not the nucleophile in the molecule. Is it due to steric hindrance?

let me start with nucleophilicity of halides. In protic polar solvent, $$\mathrm{F^-}$$ is more solvated (hydrogen bonding) than $$\mathrm{I^-}$$ and hence less reactive.
In polar aprotic solvent $$\mathrm{F^-}$$ solvation is less and therefore more reactive.
Such behavior may not be applicable here, since phenoxide is resonance stabilized while other compound is not. Therefore phenoxide $$\ce{2}$$ is less nucleophilic then cyclohexanolate $$\ce{1}$$.