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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

Treatment of a 1,3-diketone such as 2,4-pentanedione with base does not give an aldol condensation product. Explain.

The Stork enamine reaction and the intramolecular aldol reaction can be carried out in sequence to allow the synthesis of cyclohexanones. For example, the reaction of the pyrrolidine enamine of cyclohexanone with 3-buten-2-one, followed by enamine hydrolysis and base treatment, yields the product indicated. Write each step, and show the mechanism of each.

The bicyclic ketone shown below does not undergo aldol self-condensation even though it has two hydrogen atoms. Explain.

Which of the following compounds are aldol condensation products? What is the aldehyde or ketone precursor of each?

(a) 2-Hydroxy-2-methylpentanal (b) 5-Ethyl-4-methyl-4-hepten-3-one

What product would you expect to obtain from aldol cyclization of hexanedial,OHCCH2CH2CH2CH2CHO
See all solutions

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