Oxymercuration Practice Problems
Show the products of the first step of the following reaction. Explain why the stereospecificity of the oxymercuration step becomes insignificant after the reduction step.
Determine the product(s) of the oxymercuration–demercuration reaction of the following alkene:
Show the mechanism and account for the stereochemistry of the oxymercuration step of the following:
Will the following oxymercuration-reduction reaction produce an equal mixture of stereoisomers? Explain.
Suggest a possible mechanism for the oxymercuration step of the reaction given below. Take into account the stereochemistry of the products formed.
Based on the experimental results of the oxymercuration-demercuration reaction, compare the stabilities of the carbocation and the mercurinium ion given below, and suggest why one is more stable than the other.
What are the products when the following molecule reacts with (1) Hg(OAc) 2, H2O, and then with (2) NaBH4?
What are the product(s) formed when the following compound reacts with (1) Hg(OAc) 2, H2O, and then with (2) NaBH4?
Determine the products formed when the given alkene reacts with (1) Hg(OAc) 2 and H2O followed by (2) NaBH4.
Give the product(s) for the reaction of the given alkyne with H 2SO4, HgSO4, and H2O.
Write a plausible mechanism for the oxymercuration step of the following reaction:
Draw the final product when the mercurated intermediate is reduced with NaBH4.
For the following reaction, draw the products for the:
a. Mercuration step
b. Demercuration step when the product of the first step is treated with NaBH4.