Oxymercuration Video Lessons

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Concept:

Problem: Draw the structure of the major organic product of the following reaction.• You do not have to consider stereochemistry.• In cases where there is more than one answer, just draw one.

FREE Expert Solution

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.


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Problem Details

Draw the structure of the major organic product of the following reaction.

• You do not have to consider stereochemistry.
• In cases where there is more than one answer, just draw one.

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