НО. НО. (above product not formed) The Grignard reagent will deprotonate the carboxylic acid because the carboxylic acid is a stronger base than the conjugate acid of the Grignard reagent. The Grignard reagent will add to the carboxylic acid instead of the ketone because the carboxylic acid is more electrophilic. The Grignard reagent will add to both the ketone and carbonyl, and the carboxylic acid will be reduced to an alcohol with two ethyl groups attached. The wrong product is written. A methyl group should be added to the ketone carbonyl instead of an ethyl group.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 23E
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The reaction written below will not create the product that has been written. What reaction happened instead and why?
НО.
O
MgBr
HO
OH
(above product not
formed)
The Grignard reagent will deprotonate the carboxylic acid because the carboxylic acid is a stronger base than the conjugate acid of the
Grignard reagent.
The Grignard reagent will add to the carboxylic acid instead of the ketone because the carboxylic acid is more electrophilic.
The Grignard reagent will add to both the ketone and carbonyl, and the carboxylic acid will be reduced to an alcohol with two ethyl
groups attached.
The wrong product is written. A methyl group should be added to the ketone carbonyl instead of an ethyl group.
Transcribed Image Text:The reaction written below will not create the product that has been written. What reaction happened instead and why? НО. O MgBr HO OH (above product not formed) The Grignard reagent will deprotonate the carboxylic acid because the carboxylic acid is a stronger base than the conjugate acid of the Grignard reagent. The Grignard reagent will add to the carboxylic acid instead of the ketone because the carboxylic acid is more electrophilic. The Grignard reagent will add to both the ketone and carbonyl, and the carboxylic acid will be reduced to an alcohol with two ethyl groups attached. The wrong product is written. A methyl group should be added to the ketone carbonyl instead of an ethyl group.
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