Chapter 15: Alcohols, Diols and Thiols

Hydrolysis of Epoxides

Summary

• Typical reagents :  H₃O⁺ or aq. NaOH
• Reactions of epoxides are covered in more detail in Chapter 16
• Note that epoxides are more reactive than normal ethers due to the high ring strain
• The nucleophile attacks the epoxide and opens the ring by breaking the C-O bond.
• Since the nucleophile attacks at 180^o to the breaking C-O bond, the stereochemistry of the diol is trans.

This is shown by the following example:

• Reactions of Epoxides (chapter 16)
• Hydroxylation of Alkenes

© Dr. Ian Hunt, Department of Chemistry