Please show the mechanism of Oxymercuration - demercuration ? Give an example to make it understand.
1 Answer
The reaction converts an alkene to an alcohol in a Markovnikov addition. The end result is just like acid-catalyzed hydration using
The "oxymercuration" part is when the mercury complex adds on, and the "demercuration" part is when it comes off.
On an exam, you can feel free to write
Consider a general asymmetric alkene. The overall reaction is:
where each
#R# can be either#"H"# or an alkyl group (#-"CH"_3# ,#-"CH"_2"CH"_3# , etc).
If the reaction dissolves mercury(II) acetate in water, then THF (tetrahydrofuran) is also needed.
Here's the mechanism:
1. The mercury(II) acetate complexes onto the alkene, just like in bromination (
It's a two-way street - Here, mercury donates its
2. Nucleophilic attack occurs via the alcohol (
3. Fortunately, this acid-base equilibrium favors the weak acetic acid over the alcohol (
4. This last step is the demercuration, i.e. the reduction of the