Question & Answer: The Claisen Condensation is a special form of the aldol condensation in that instead of…..

1) The Claisen Condensation is a special form of the aldol condensation in that instead of aldehydes, this condensation uses esters as starting materials. From past experience, you know that you can either add once with an anionic nucleophile (to receive a ketone) or twice (to form an alcohol). If the anion is the limiting reagent however, the anion will only add once as shown by the reaction below. 0 0 HOCH3 limiting excess An important consequence of this reaction is that you obtain a -dicarbonyl as product. The (-ecarbon of each of these carbonyls is much more acidic than the starting material esters Propose a synthesis using the Claisen condensation for each of the molecules below. /6 HOCHs O. 0 /6 HOCH HOCH

The Claisen Condensation is a special form of the aldol condensation in that instead of aldehydes, this condensation uses esters as starting materials. From past experience, you know that you can either add once with an anionic nucleophile (to receive a ketone) or twice (to form an alcohol). If the anion is the limiting reagent however, the anion will only add once as shown by the reaction below. An important consequence of this reaction is that you obtain a – dicarbonyl as product. The -carbon of each of these carbonyls is much more acidic than the starting material esters. Propose a synthesis using the Claisen condensation for each of the molecules below.

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