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Chapter 22: Q4P (page 734)

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

Short Answer

Expert verified

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 by step solution

01

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.

02

Enolate ion formation

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

03

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.

04

Conclusion

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

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Most popular questions from this chapter

When an optically active carboxylic acid such as (R)-2-phenylpropanoic acid is brominated under Hell–Volhard–Zelinskii conditions, is the product optically active or racemic? Explain.


The two optically beta-keto acids below were decarboxylated using the conditions typically used for the acetoacetate synthesis. Will the ketone products also be optically active? Provide the complete mechanism to explain your answer.

How would you prepare the following compounds using either an Acetoacetic ester synthesis or a malonic ester synthesis?

When a ketone is treated with acid and a halogen, the a-monohalogenated product can be obtained in high yield. However, under basic conditions it is extremely difficult to isolate the mono halogenated product. Provide an explanation for this reactivity.

Question: How would you prepare the following compound using an acetoacetic ester synthesis?
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