Q4P - Organic Chemistry (Mcmurry)

Question

Write the complete mechanism for the deuteration of acetone on treatment with D₃O⁺.

Step-by-Step Solution

Answer

Step 1: Explanation of the process

The reaction of acetone with D₃O⁺ is a two step process. The first step is enolate ion formation. In the second step the enolate ion reacts with deuterium ion and forms the product.

Step 2: Enolate ion formation

In this step, one of the Hydrogen ions of acetone is removed by the deuterium ion and forms the enolate ion.

Step 3: Product formation

In this step, the enolate reacts with the deuterium ion. For this, the double bond between the carbon atoms is broken and the deuterium forms bond with the carbon atom.

Step 4: Conclusion

Hence, the mechanism of deuteration of acetone on treatment with D₃O⁺ is