Some Reactions of Epoxides

Epoxides can undergo acid or base-catalyzed ring-opening reactions. If the epoxide used in the reaction is symmetric, the product will be the same under both conditions. But the products will be different, if the epoxide is unsymmetric. 

OH More stable (lower transition state energy) 

In a base-catalyzed ring opening of an epoxide, the nucleophilic attack is on the less substituted (less hindered) carbon atom in the epoxide ring. The mechanism is shown below. 

All the reactions described below CANNOT prepare ethers, EXCEPT  

In terms of boiling point, ethers most resemble which of the following types of compounds  

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Some reactions of epoxides with fluoride and perfluoroalkoxide ions were referred to in Section IB, Subsection 2 (above), and the importance of polymers of these systems was stressed. There are numerous publications or patents concerning the S3mthesis of these... 

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