THF is used as a solvent for Grignard reagents, but epoxides react with Grignard reagents. There is only a small difference between epoxides and THF, what causes the difference in reactivity towards Grignard reagents?


1 Answer 1


The difference between THF and epoxides is perhapse bigger than you might think. Due to the three-membered-ring of an epoxide, a lot of energy is 'stored' in ring strain. This destabilizes the stucture and is a driving force for a Grignard reaction (or any substitution on an epoxide).

The THF is a five-membered-ring, which is far more stable. This bond is simply an ether, that happens to be in a cyclic structure. Therefore it also reacts like an ether: not easily attacked by nucleophiles.


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