Q14P

Question

What product would you expect from the following reaction?



Step-by-Step Solution

Verified
Answer

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

Ethyl 4-methyl 2-oxocyclohexanecarboxylate.

1The 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.

2Cyclization of 1,7-diesters in the presence of N a + - O E t , and H 3 O +

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