# What is the nucleophile in alkaline hydrolysis of a haloalkane?

We know that haloalkanes are able to undergo $\mathrm{S_N1}$ or $\mathrm{S_N2}$ in alkaline hydrolysis, and the hydroxide ion is the nucleophile responsible for attack. But when we talk about hydrolysis, isn't it a reaction with water? Where does the hydroxide ion that attacks the haloalkane really come from; the water, or the alkaline catalyst?

(1) If this reaction occurs via the $\mathrm{S_N2}$ mechanism, a one-step displacement mechanism, you are correct to say that hydroxide (being a much better nucleophile than neutral water) is the nucleophile attacking carbon.
(2) If the reaction occurs via the $\mathrm{S_N1}$ mechanism (note that which mechanism is preferred depends on the structure of the haloalkane, and in some cases a haloalkane can react via both mechanisms), you have a two-step process in which the haloalkane initially dissociates (a slow step) to form a carbocation plus halide ion. The carbocation then reacts very rapidly with whatever nucleophile is handy to form the alcohol. Water is likely more abundant than hydroxide, and is a strong enough nucleophile to react instantly with a carbocation, so most of the product will be formed that way, with release of $\ce{H+}$, rather than by combination of the carbocation directly with hydroxide. The $\mathrm{S_N1}$ reaction of a haloalkane in this manner with excess water or other polar solvent is often referred to as a "solvolysis" reaction.