H3CO cat. Cu2+ CH3OH (aq) 7 8 cat. Cu2+ no reaction CH3OH (aq) & CO2 9 a. Provide a mechanism to account for the fact that Cu²+ catalyzes this reaction. b. In one sentence explain why Cu²+ does not similarly catalyze the decarboxylation of 9.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
Problem 25MP: Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of...
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Consider the decarboxylation of dimethyloxaloacetate 7 to 3-methyl-2-oxobutyrate 8 shown below 

H3CO
cat. Cu2+
CH3OH (aq)
7
8
cat. Cu2+
no reaction
CH3OH (aq)
& CO2
9
a. Provide a mechanism to account for the fact that Cu²+ catalyzes this reaction.
b. In one sentence explain why Cu²+ does not similarly catalyze the decarboxylation
of 9.
Transcribed Image Text:H3CO cat. Cu2+ CH3OH (aq) 7 8 cat. Cu2+ no reaction CH3OH (aq) & CO2 9 a. Provide a mechanism to account for the fact that Cu²+ catalyzes this reaction. b. In one sentence explain why Cu²+ does not similarly catalyze the decarboxylation of 9.
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