Question

Why is is possible to convert alkyl halides to alcohols with NaOH but the conversion of alcohols to alkyl halides with NaCl is not possible?

Answer 1

`"Cl"^{-}` is more stable than `"OH"^{-}`, so `"Cl"^{-}` is the preferred leaving group.

Explanation:

We can also say that `"OH"^{-}` is a stronger nucleophile than `"Cl"^{-}`.

Strong base such as `"OH"^{-}` tend to make poor leaving group, due to their inability to stabilize a negative charge.