Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

Question
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
ОН
HСI (aq)
expand button
Transcribed Image Text: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 ОН HСI (aq)
Expert Solution
Check Mark
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY