What is the product of the Dieckmann-like condensation of this ketoester, IV V

Question

What is the product of the Dieckmann-like condensation of this ketoester,  IV V

Quizplus · Accepted Answer

The Dieckmann condensation involves intramolecular nucleophilic acyl substitution, whereby the alkoxide ion formed from the deprotonation of the alpha-carbon attacks the carbonyl carbon forming a cyclic intermediate that subsequently will collapse with the expulsion of the leaving group to form a beta-ketoester. The starting material, 11eaa4bc_3e26_3667_9180_43d159098f1f_TB5902_00 IV V, has a 7-carbon chain with two ester functional groups, and the alpha-carbon is between the two ester groups, making it a suitable candidate for intramolecular nucleophilic acyl substitution. The cyclic intermediate could then collapse to form a 6-membered ring, which would be the beta-ketoester product III. Thus, the answer is C.

What Is the Product of the Dieckmann-Like Condensation of This