I remember that one of my old organic chemistry profs referred to mercury as being a "fancy proton". I think it was in the context of oxymercuration reduction.
What might have been his rationale for offering this comparison?
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It is a large, soft, Lewis acid. One can use protic acid and water to promote the same reaction, but the product distribution can sometimes be different. In the oxymercuration reaction Hg can form a pi complex with alkenes or alkynes, and these "bridged" cations will not undergo rearrangments to the extent that those produced by protic acids might. Bottom line - they're both essentially performing the same function in this reaction - activating the pi bond towards attack - but the oxymercuration is milder. |
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