Oxymercuration-Reduction

Definition

Oxymercuration-reduction is a two-step organic reaction that is used to convert alkenes into alcohols. It involves the initial addition of a mercury-containing compound, followed by the reduction of the resulting mercurinium ion intermediate to form the final alcohol product.

5 Must Know Facts For Your Next Test

1. Oxymercuration-reduction is a two-step reaction that converts alkenes into alcohols.
2. The first step, oxymercuration, involves the addition of a mercury-containing compound, such as mercury(II) acetate, across the carbon-carbon double bond of the alkene.
3. The resulting mercurinium ion intermediate is then reduced in the second step, typically using sodium borohydride, to form the final alcohol product.
4. Oxymercuration-reduction is a regioselective reaction, meaning the alcohol group is formed on the more substituted carbon of the alkene.
5. This reaction is useful for the synthesis of alcohols from alkenes, as it provides a controlled and predictable way to introduce the hydroxyl group.

Review Questions

• Explain the purpose and significance of the oxymercuration-reduction reaction in the context of 8.5 Hydration of Alkenes: Addition of H2O by Hydroboration.
  • The oxymercuration-reduction reaction is a key method for the hydration of alkenes, which is covered in Section 8.5. In this reaction, the alkene is first converted to a mercurinium ion intermediate through the addition of a mercury-containing compound. This intermediate is then reduced to form the final alcohol product. The significance of this reaction is that it provides a regioselective way to introduce a hydroxyl group onto the more substituted carbon of the alkene, allowing for the controlled synthesis of specific alcohol products from alkene starting materials.
• Describe how the oxymercuration-reduction reaction can be utilized in the context of 9.9 An Introduction to Organic Synthesis.
  • The oxymercuration-reduction reaction is an important tool in organic synthesis, as it allows for the conversion of alkenes into alcohols, which are versatile functional groups that can be further manipulated. In the context of Section 9.9, which discusses the general principles of organic synthesis, the oxymercuration-reduction reaction can be used as a key step in the synthesis of more complex organic molecules. By starting with an alkene and selectively converting it to an alcohol, the synthetic chemist can then explore a variety of subsequent reactions and transformations to build up the desired target compound.
• Evaluate the advantages and limitations of the oxymercuration-reduction reaction compared to other methods for the hydration of alkenes.
  • The oxymercuration-reduction reaction offers several advantages over other methods for the hydration of alkenes, such as the ability to achieve regioselectivity and the mild reaction conditions. However, it also has some limitations. The advantages include the predictable formation of the more substituted alcohol product, the use of relatively mild reagents, and the ability to control the stereochemistry of the final alcohol. The limitations include the use of mercury-containing compounds, which can be toxic, and the potential for side reactions or over-reduction. Overall, the oxymercuration-reduction reaction is a powerful tool in organic synthesis, but the choice of method will depend on the specific requirements of the synthetic target and the available starting materials.

Related terms

Alkene: An unsaturated hydrocarbon compound containing a carbon-carbon double bond.

Mercurinium Ion: An intermediate species formed during the oxymercuration step, where a mercury-containing compound adds across the carbon-carbon double bond.

Reduction: A chemical reaction where electrons are gained, typically resulting in the lowering of an atom's oxidation state.