Question

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

Short answer

Step 1: The given compound

Step-by-step solution

The given compound

Step 1: The given compound

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.

Conclusion

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