Concept explainers
Oxymercuration
Concerns about mercury’s toxicity have led to decreased use of mercury-based reagents in
Among the synthetically useful reactions of
The reaction is performed in two operations, the first of which is oxymercuration. In this stage the alkene is treated with
From the overall reaction, we see that oxymercuration–demercuration
1. accomplishes hydration of the double bond in accordance with Markovnikov’s rule, and
2. carbocation rearrangements do not occur.
Additional information from stereochemical studies with other
3. anti addition of
4. the replacement of
The structure of the intermediate in oxymercuration has received much attention and can beapproached by considering what is likely to happen when the electrophile
Recall from Section
The electrons in a
The problems that follow explore various synthetic aspects of oxymercuration–demercuration.Experimental procedures sometimes vary depending on the particular transformation. The source of the electrophile may be a mercury(II) salt other than
Oxymercuration–demercuration of
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Organic Chemistry - Standalone book
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning