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Organic Chemistry 2

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Moderate

Dieckmann Condensation Retrosynthesis

ORGO2-HHBWYF

The Claisen condensation and its intramolecular variant (the Dieckmann condensation) are frequently used for carbon-carbon bond formation in organic chemistry.

The Claisen condensation also resembles the key carbon-carbon bond forming events in fatty acid and terpene biosynthesis.

The Claisen condensation features numerous mechanistic steps, including deprotonation of an alpha hydrogen in an ester, followed by nucleophilic addition of the resulting enolate to another ester group, loss of the OR group from the ester, and deprotonation of the resulting highly acidic beta-ketoester.

Determine which diester is required for the formation of the indicated product under Claisen/Dieckmann condensation conditions.

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A

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B

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C

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D

Created for Albert.io. Copyright 2016. All rights reserved.