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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Vrig on January 22, 2013, 11:41:45 AM

Title: Why is it possible to transmetallate i-PrMgBr with PhBr but not the other way?
Post by: Vrig on January 22, 2013, 11:41:45 AM

Q: Why is it possible to transmetallate i-PrMgBr with PhBr to generate i-PrBr and PhMgBr, but not the other way around?

I suspect that it has something to do with the hybridization of i-Pr vs Ph (Ph would have a more stable anion, which pKa also shows) but I don't understand how it would effect the mechanism unless the intermediate is a phenylic anion?