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Chapter 23: Q10P (page 764)

What product would you expect to obtain from the base treatment of 1,6-cyclo-decanedione?

Short Answer

Expert verified

It gives seven-member ring fused with the five-member ring.

Step by step solution

01

Intramolecular aldol condensation:


02

Removal of a water molecule on heating and formation of double bond:

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Most popular questions from this chapter

Show how you would synthesize the following compound using an aldol reaction:

How could you prepare the following cyclohexanones by combining a Stork enamine reaction with an intramolecular aldol condensation? (See Problem 23-64.)

In contrast to the rapid reaction shown in Problem 23-60, ethyl acetoacetate requires a temperature over 150 °C to undergo the same kind of cleavage reaction. How can you explain the difference in reactivity?

The compound known as Hagemann’s ester is prepared by treatment of a mixture of formaldehyde and ethyl acetoacetate with base, followed by acid-catalyzed decarboxylation.

(a)The first step is an aldol-like condensation between ethyl acetoacetate and formaldehyde to yield an α,β-unsaturated product. Write the reaction, and show the structure of the product.

(b)The second step is a Michael reaction between ethyl acetoacetate and the unsaturated product of the first step. Show the structure of the product.

What enone product would you expect from aldol condensation of each of the following compounds?
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