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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

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.

Why do you suppose ketone halogenations in acidic media are referred to as being acid-catalyzed,whereas halogenations in basic media are base-promoted? In other words, why is a full equivalent of base required for halogenation?

Show the steps in preparing each of the following substances using either a malonic ester synthesis or an acetoacetic ester synthesis:

.

How many acidic Hydrogens does each of the molecules listed in Problem 22-1 have? Identify them.

Fill in the reagents a–c that are missing from the following scheme:
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