Solvolysis

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In organic chemistry, solvolysis is a special type of nucleophilic substitution where the nucleophile is a solvent molecule. Some common solvents/nucleophiles in solvolysis reactions are alcohols, such as methanol, and water. The reaction mechanism for this chemical reaction is an S_N1 reaction.

Solvolysis of a chiral reactant results in the racemate (as expected in S_N1) but is often accompanied by Walden inversion. This is explained by postulating an intimate ion pair whereby the leaving anion is still in proximity to the carbocation and effectively shielding it from an attack by the nucleophile.