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Chapter 23: Q14P (page 770)

What product would you expect from the following reaction?

Short Answer

Expert verified

The product is formed when diethyl 4-methyl heptane dioate is

Ethyl 4-methyl 2-oxocyclohexanecarboxylate.

Step by step solution

01

The given reaction followed the Dieckmann cyclization:

In which Intramolecular Claisen condensations can be carried out with diesters, just as intramolecular aldol condensations can be carried out with diketones.

This reaction works best on 1,6-diesters and 1,7-diesters.

02

Cyclization of 1,7-diesters in the presence of Na+-OEt, and H3O+

diethyl 4-methyl heptane dioate Ethyl 4-methyl 2-oxocyclohexanecarboxylate

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Most popular questions from this chapter

The Darzens reaction involves a two-step, base-catalyzed condensation of ethyl chloroacetate with a ketone to yield an epoxy ester. The first step is a carbonyl condensation reaction, and the second step is an SN2 reaction. Write both steps, and show their mechanisms.

The following structure represents an intermediate formed by the addition of an ester enolate ion to a second ester molecule. Identify the reactant, the leaving group, and the product.

The following molecule was formed by an intramolecular aldol reaction. What dicarbonyl precursor was used for its preparation?

Propose a mechanism to account for the following reaction of an enamine with an alkyl halide:

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?
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