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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

Propose a mechanism for the following base-catalyzed isomerization:

Fill in the missing reagents a鈥揾 in the following scheme:

Predict the addition product for each reaction below and provide the mechanism.

Which of the following compounds can probably be prepared by a mixed aldol reaction? Show the reactants you would use in each case.

In the mixed Claisen reaction of cyclopentanone with ethyl format, a much higher yield of the desired product is obtained by first mixing the two carbonyl components and then adding a base, rather than by first mixing base with cyclopentanone and then adding ethyl format. Explain.
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