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🥼organic chemistry review

Mercury(II) Acetate

Written by the Fiveable Content Team • Last updated September 2025
Written by the Fiveable Content Team • Last updated September 2025

Definition

Mercury(II) acetate, also known as basic mercuric acetate, is a chemical compound with the formula Hg(CH3COO)2. It is a white crystalline solid that is commonly used as a reagent in organic chemistry reactions, particularly in the hydration of alkenes and the preparation of alcohols.

5 Must Know Facts For Your Next Test

  1. Mercury(II) acetate is a key reagent in the oxymercuration reaction, which is used to add water to alkenes, forming alcohols.
  2. The oxymercuration reaction involves the addition of the mercury(II) acetate and water to the alkene, followed by the removal of the mercury group to yield the final alcohol product.
  3. The use of mercury(II) acetate in the oxymercuration reaction allows for the regio- and stereoselective formation of alcohols, making it a valuable tool in organic synthesis.
  4. In the preparation of alcohols, mercury(II) acetate can be used as an intermediate to form the desired alcohol product, often in a more efficient and selective manner than other methods.
  5. The use of mercury(II) acetate in organic reactions requires careful handling due to the toxicity of mercury compounds, and appropriate safety precautions must be taken.

Review Questions

  • Explain the role of mercury(II) acetate in the hydration of alkenes through the oxymercuration reaction.
    • Mercury(II) acetate is a key reagent used in the oxymercuration reaction, which is a method for the hydration of alkenes to form alcohols. The reaction involves the addition of the mercury(II) acetate and water to the alkene, forming an intermediate mercurinium ion. This intermediate is then reduced, typically using a reducing agent like sodium borohydride, to remove the mercury group and yield the final alcohol product. The use of mercury(II) acetate in this reaction allows for the regio- and stereoselective formation of alcohols, making it a valuable tool in organic synthesis.
  • Describe how mercury(II) acetate can be used in the preparation of alcohols, and discuss the advantages of this approach compared to other methods.
    • Mercury(II) acetate can be used as an intermediate in the preparation of alcohols. In this approach, the mercury(II) acetate is first added to an alkene, forming an organo-mercury compound. This intermediate can then be further transformed, often through reduction, to yield the desired alcohol product. The use of mercury(II) acetate in this process can be advantageous compared to other methods, as it can allow for more efficient and selective alcohol formation. Additionally, the use of mercury(II) acetate can provide access to alcohols that may be difficult to obtain through alternative synthetic routes. However, the use of mercury compounds requires careful handling due to their toxicity, and appropriate safety precautions must be taken.
  • Evaluate the importance of mercury(II) acetate in the context of organic chemistry, considering its applications in both the hydration of alkenes and the preparation of alcohols, as well as the potential challenges associated with its use.
    • Mercury(II) acetate is a versatile and important reagent in organic chemistry, with applications in both the hydration of alkenes and the preparation of alcohols. Its use in the oxymercuration reaction allows for the regio- and stereoselective formation of alcohols, making it a valuable tool in organic synthesis. Additionally, the use of mercury(II) acetate as an intermediate in the preparation of alcohols can provide access to products that may be difficult to obtain through other methods. However, the use of mercury compounds, such as mercury(II) acetate, requires careful handling due to their toxicity, and appropriate safety precautions must be taken. The potential challenges associated with the use of mercury(II) acetate, including its environmental and health impacts, must be weighed against the synthetic advantages it can provide in organic chemistry reactions.