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Chapter 22: 15P (page 728)

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

Short Answer

Expert verified

Step 1: The given compound

Step by step solution

01

The given compound

Step 1: The given compound

02

Explanation

The base ethoxide ion abstracts a proton from the methylene group and forms an enolate ion.

Then the enolate ion attacks 1,4-dibromobutane and displaces a bromide ion.

Then again the ethoxide ion abstracts second proton from the methylene group and forms another enolate ion.

Then the enolate ion attacks the other end of the 1,4-dibromobutane and displaces a bromide ion.

Thus the cyclic keto ester forms.

Then hydrolysis of the keto ester with dilute acids and decarboxylation by heating forms the required product.

03

Conclusion

Thus you can prepare the given compound using an acetoacetic ester synthesis.

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Most popular questions from this chapter

Unlike most 尾-diketones, the following 尾-diketone has no detectable enol content and is about as acidic as acetone. Explain.

Rank the following compounds in order of increasing acidity:

How would you synthesize the following compounds from cyclohexanone?

More than one step may be required.

How could you use a malonic ester synthesis to prepare the following compound?

Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction.For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. Propose a mechanism.
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