Opening of epoxides with nucleophiles under acidic conditions

by James

Description: When acid is added to epoxides, nucleophiles will add to the more substituted position. The stereochemistry of the addition is trans.
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{ 5 comments… read them below or add one }


So helpful thank you!!!!


Jeremy McMurray

Sir does the methyl substituent have any stereochemistry at the end?



yes, it is “up” in the example shown in the mechanism. The fact that OH is drawn as a “dash” implies that the methyl group is a “wedge” (up) although I was lazy and did not draw it in as such.
The reaction proceeds with inversion of configuration.


veralyn v

is this considered sn2?



It’s a bit like an SN1, except with inversion of stereochemistry. It’s very similar to the second step in bromination or chlorination of alkenes, where the nucleophile attacks the charged 3-membered ring intermediate.


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