Dolbier HW Solutions 316

Dolbier HW Solutions 316 - 410 ETHERS, EPOXIDES, AND...

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The ether product has the same absolute con f guration as the starting alkoxide because no bonds to the stereogenic center are made or broken in the reaction. ( c ) Vicinal halohydrins are converted to epoxides on being treated with base. ( d ) The reactants, an alkene plus a peroxy acid, are customary ones for epoxide preparation. The reaction is a stereospeci f c syn addition of oxygen to the double bond. ( e ) Azide ion is a good nucleophile and attacks the epoxide function. Substitution occurs at carbon with inversion of con f guration. The product is trans -2-azidocyclohexanol. ( f ) Ammonia is a nucleophile capable of reacting with epoxides. It attacks the less hindered car- bon of the epoxide function. Aryl halides do not react with nucleophiles under these conditions, and so the bromine sub-
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