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.

Identify the reagents needed for the following reaction.

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.

Determine the product of the given reaction.

Which reagent can be used for the following hydration reaction?

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.

For the following reaction, draw the structure of the major product:

Draw the structures of intermediates, if there are any. If applicable, include the stereochemistry of the final product.

True or false. The given reaction would result in an equal mixture of stereoisomers as products.

Sketch the product of the reaction below.

The synthesis of compound B from compound A involves the reaction:

where R represents a complex cyclic group. Predict compound B.

Determine the most probable single product of the following oxymercuration–reduction reaction. [Don’t worry about the absolute stereochemistry, though these reactions are also stereoselective.]

Oxymercuration-reduction can also be used to generate cyclic esters as shown below. Show the most probable mechanism for this reaction. 

Oxymercuration-reduction can be utilized in the production of ethers, like an acid-catalyzed hydration. Give an alkene and the proper reaction conditions to create the ether below.

Determine the product of the given oxymercuration–reduction reaction. [Note: No need to worry about stereochemistry.]

Producing tetrahydrofurans is a major objective in synthetic organic chemistry because many anticancer natural products contain it. Provide a mechanism for this reaction.

Propose a synthesis for the compound shown below using 1-methylcyclopent-1-ene as the starting molecule.

Propose a synthesis for the conversion of vinylcyclohexane to 1-cyclohexylethanol. Explain why acid-catalyzed hydration is not the best option for this conversion.

Predict the plausible major product(s).

(i) 1-methylcyclopent-1-ene + Hg(OAc)₂ in CH₃OH

(ii) The product from part (i), treated with NaBH₄

Propose a plausible synthesis that would accomplish the given conversions.

(i) prop-1-ene → 2-methoxypropane

(ii) 1-bromo-2-methylcyclohexane → 1-methylcyclohexanol