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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{ 3 comments… read them below or add one }

sam

So helpful thank you!!!!

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Jeremy McMurray

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

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james

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.

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