Recall that alkenes are converted to alcohols via oxymercuration-reduction:
This occurs in three steps:
(1) electrophilic addition – the alkene attacks Hg(OAc)2, forming the cyclic mercurinium ion. Since a cyclic intermediate is formed, rearrangement is not possible for this reaction.
(2) nucleophilic attack – water attacks the cyclic mercurinium ion. This follows Markovnikov’s rule, where water attacks the more-substituted carbon. The stereochemistry of this reaction is anti, where –OH and –HgOAc will be trans to each other.
(3) reduction – NaOH and NaBH4 react with the intermediate to form the alcohol.
Draw structural formulas for all alkenes that could be used to prepare the alcohol shown below by oxymercuration.
• You do not have to consider stereochemistry.
• Include only alkenes that will give the alcohol as the single major product.
• Separate structures with + signs from the drop-down menu.
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