Oxymercuration reaction

The oxymercuration reaction is a chemical reaction used in organic chemistry to form a neutral alcohol without any rearrangement of carbocations. In this reaction, similar to some other organic reactions, the Hg²⁺ ion works to stabilize the molecule to prevent carbocation formation and so prevents rearrangement. The reaction results in a product that follows Markovnikov's rule.

The general equation for the reaction is as follows:

C=C in H₂O / THF with Hg(OAc)₂, and then with NaBH₄, → HO-C-C-H

Strictly speaking, only the first step is oxymercuration, but in practice this is nearly always followed by demercuration with NaBH₄ (the second step).

See also: Oxymercuration reaction, Carbocation, Chemical reaction, Ion, Markovnikov's rule, Mercury (element), Organic chemistry, Organic reaction, Sodium borohydride