Dolbier HW Solutions 310

Dolbier HW Solutions 310 - 404 ETHERS, EPOXIDES, AND...

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16.11 The cis epoxide is achiral. It is a meso form containing a plane of symmetry. The trans isomer is chiral; its two mirror-image representations are not superposable. Neither the cis nor the trans epoxide is optically active when formed from the alkene. The cis epox- ide is achiral; it cannot be optically active. The trans epoxide is capable of optical activity but is formed as a racemic mixture because achiral starting materials are used. 16.12 ( b ) Azide ion is a good nucleophile, reacting readily with ethylene oxide to yield 2-azidoethanol. ( c ) Ethylene oxide is hydrolyzed to ethylene glycol in the presence of aqueous base. ( d ) Phenyllithium reacts with ethylene oxide in a manner similar to that of a Grignard reagent. ( e ) The nucleophilic species here is the acetylenic anion CH 3 CH 2 C > C : 2 , which attacks a carbon atom of ethylene oxide to give 3-hexyn-1-ol. 16.13 Nucleophilic attack at C-2 of the starting epoxide will be faster than attack at C-1, because C-1 is more sterically hindered. Compound A, corresponding to attack at C-1, is not as likely as com-
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