Mercury(II) acetate

Mercury(II) acetate is the chemical compound with the formula Hg(O2CCH3)2. Commonly abbreviated Hg(OAc)2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors.

Arenes undergo "mercuration" upon treatment with Hg(OAc)2. The one acetate group that remains on mercury can be displaced by chloride:
 * C6H5OH +  Hg(OAc)2  →  C6H4(OH)-2-HgOAc  +  HOAc
 * C6H4(OH)-2-HgOAc +  NaCl  →  C6H4(OH)-2-HgCl  +  NaOAc

The Hg2+ center binds to alkenes, inducing the addition of hydroxide and alkoxide. For example, treatment of methylacrylate with mercuric acetate in methanol gives an α--mercuri ester:
 * Hg(OAc)2 +  CH2=CHCO2CH3  +  CH3OH  →  CH3OCH2CH(HgOAc)CO2CH3  +  HOAc

Mercury(II) has a high affinity for sulfur ligands. Hg(OAc)2 can be used as a reagent to remove the acetamidomethyl protecting group, which is used to "protect" thiol groups in organic synthesis. Similarly Hg(OAc)2 is a standard reagent to convert thiocarbonate esters into dithiocarbonates:
 * (RS)2C=S +  H2O  +  Hg(OAc)2  →  (RS)2C=O  +  HgS  +  2 HOAc  +  "HgO"