Acid Catalyzed Hydrolysis of Epoxides

• Stereospecifc (Trans)

• Ring opening

• Net Reaction

• Mechanism

  • Positive charge distributed over Oxygen and two carbons
  • H2O molecule as nucleophile attaches to more substituted ring Carbon

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Net Reaction

OH

H+ |

R-CH-CH-R’ + H2O -----> R-CH-CH-R’

\ / |

O OH

Reaction Mechanism

1. R-CH-CH-R’ + H+ ----> R-CH-CH-R’

\ / \ /

O + O-H

O+H2 OH

| |

2. R-CH-CH-R’ + H2O ----> R-CH-CH-R’ -------> R-CH-CH-R’ + H+

\ / | |

O OH OH