Epoxides react with nucleophiles on the less substituted side in basic conditions. This will invert the stereochemistry at the reacting carbon and will not invert the stereochemistry at the non-reacting carbon. This is a SN2 mechanism.多重下拉选择题

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Epoxides react with nucleophiles on the more substituted side in acidic conditions. This will invert the stereochemistry at the reacting carbon and will not invert the stereochemistry at the non-reacting carbon. This is a SN2 mechanism.

Which of these would be considered a basic nucleophile for reaction with an epoxide? (Select all that apply)

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