Question

oxymercuration–demercuration

The only  part I got correct was step 3 in part b. I really need help understanding this question.


There are several reagents that can be used to effect addition to a double bond, including: acid and water, oxymercuration–demercuration reagents, and hydroboration–oxidation reagents.

The transformation shown utilizes oxymercuration–demecuration conditions.

The starting material is a 5 carbon chain where there is a double bond between carbons 1 and 2 and a methyl substituent on carbon 3. The first step reacts with Mercury diacetate in T H F and water. The second step reacts with sodium borohydride and hydroxide. The product is a 5 carbon chain where carbon 2 has a hydroxy group and carbon 3 has a methyl group.

Inspect the final product and select all the reasons why oxymercuration–demercuration was chosen to effect the following transformation instead of the other reagents.

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b. Complete the mechanism for the reaction by adding curved arrows. Note, the acetate ion is a spectator throughout.


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