Master Organic Chemistry Reaction Guide

Opening of epoxides with nucleophiles under acidic conditions

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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Real-World Example:
Org. Synth. 1926, 6, 12
DOI Link: 10.15227/orgsyn.006.0012

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Comment section

5 thoughts on “Opening of epoxides with nucleophiles under acidic conditions

    1. 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.

    1. 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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