Why is Mercury acetate an electrophile?

[wacki]

Mercury is a metal. Metals love to lose electrons. Just trying to figure out why it's an electrophile in oxymercuration demercuration.

---

Members don't see this ad.

 

[hawkeye712]

Wouldn't the mercury have a partial positive charge?

 

[Illfavor]

I recall Hg(OAc)2 having a (+) on the mercury.

 

[wacki]

Ya but it's not charged + while both acetates are attached. It's got a 1/2 filled octet but that's about it.

 

[Cool Beans]

Mercury acetate partially dissociates leaving mercury with a positive charge as Illfavor remembered:

Hg(OAc)2 --> +HgOAc + OAc-

And as far as your original comment about metals loving to lose electrons; metals in their elemental form (the zero oxidation state) will generally easily lose electrons to form cations. But the mercury in mercury acetate is in the +2 oxidation state and is already a cation.

Hope this helps!