# Reaction of grignard with beta Keto ester [closed]

A reaction takes place between $$\ce {CH3COCH2COOC2H5}$$ with 4-chlorophenyl magnesium bromide, followed by acidic work-up. What will be major product of the reaction? Would the product be the same as the original $$\beta$$-keto ester due to the active methylene group, at which the acidic doubly-$$\alpha$$ $$\ce {H}$$ gets deprotonated?

## closed as off-topic by Avnish Kabaj, Jon Custer, A.K., aventurin, TyberiusNov 27 '18 at 1:35

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• It would be helpful if you could provide illustration of these molecules. Also, could you also provide your thoughts on the matter? – Tan Yong Boon Nov 26 '18 at 9:11
• You will get the ethyl acetoacetate back. It is sufficiently acidic (pKa ~11) to quench the Grignard and form the Mg salt of acetoacetate. – Waylander Nov 26 '18 at 14:17
• @Waylander What counts as sufficiently acidic? For example, why isn't the alpha H of a ketone deprotonated by grignard? – Tan Yong Boon Nov 26 '18 at 15:24
• I don't know precisely where to draw the line, somewhere around 18/19 perhaps. EtOH (pKa 15.9) and tBuOH (17.9) quench Grignards. Acetone (pKa 19.2) certainly undergoes Grignard addition readily enough. – Waylander Nov 26 '18 at 15:46
• @Tan Yong Boon: Plenty of examples exist where enolization of ketones competes with addition upon treatment with Grignard reagents and organolithium reagents. – user55119 Nov 26 '18 at 16:53