Question

Why sn2 reactions occurs readily in secondary ethers?

Answer 1

As hydrogen atoms are replaced one by one going from a methyl group to a tertiary halide, the reaction becomes slower because the nucleophile cannot easily reach the electrophilic carbon of the substrate. The electron density maps for these alkyl halides show this effect.

Answer 2

As hydrogen atoms are replaced one by one going from a methyl group to a tertiary halide, the reaction becomes slower because the nucleophile cannot easily reach the electrophilic carbon of the substrate. The electron density maps for these alkyl halides show this effect.