Step 4: Decarboxylation In the final step to synthesize dimedone, the carboxylic acid is heated in aqueous HCl to promote decarboxylation (Ch. 21.5, Klein). Draw the arrow pushing mechanism using the following prompts: e. First, protonate the carboxylate anion. f. Redraw the structure of the keto acid so that the OH group of the carboxylic acid is positioned near the ketone carbonyl. The hydrogen of the OH group will hydrogen bond to the carbonyl oxygen of the ketone. g. Push arrows in such a way that CO2 is lost from the molecule, and the enol form of dimedone is generated. This enol form tautomerizes to form the 1,3-diketone. Decarboxylation OH HCI (aq)

Step 4: Decarboxylation In the final step to synthesize dimedone, the carboxylic acid is heated in aqueous HCl to promote decarboxylation (Ch. 21.5, Klein). Draw the arrow pushing mechanism using the following prompts: e. First, protonate the carboxylate anion. f. Redraw the structure of the keto acid so that the OH group of the carboxylic acid is positioned near the ketone carbonyl. The hydrogen of the OH group will hydrogen bond to the carbonyl oxygen of the ketone. g. Push arrows in such a way that CO2 is lost from the molecule, and the enol form of dimedone is generated. This enol form tautomerizes to form the 1,3-diketone. Decarboxylation OH HCI (aq)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.38P

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