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Addition of Grignard on an ester
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[QUOTE="chemisttree, post: 6581038, member: 63073"] For the mechanism you have proposed for #2… this is a hemiketal. It is not a happy camper. You can force it to become a ketal (two -OR groups) under desiccating conditions and in the presence of more alcohol but you have just finished adding water and there is little free alcohol around! Hemiketals decompose back to their ketone origins in the presence of water. Actually there is an equilibrium between the ketone/alcohol and hemiketal but it is heavily weighted toward the ketone/alcohol. #1 is correct. Don’t forget that the MgBr[sup]+[/sup] is nearby to assist the alkoxide leaving. So the normally poor OR[sup]-[/sup] leaving group has some help both from the soon-to-be carbonyl oxygen’s lone pair and the metal salt. [/QUOTE]
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Addition of Grignard on an ester
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