Dolbier HW Solutions 322 - 416 ETHERS EPOXIDES AND SULFIDES...

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The reaction of 1,3-cyclohexadiene with ethylene gives the desired substance. 1,3-Cyclohexadiene is one of the given starting materials. Ethylene is prepared from ethanol. ( f ) Retrosynthetic analysis reveals that the desired target molecule may be prepared by reaction of an epoxide with an ethanethiolate ion. Styrene oxide may be prepared by reaction of styrene with peroxyacetic acid. The necessary thiolate anion is prepared from ethanol by way of the corresponding thiol. Reaction of styrene oxide with sodium ethanethiolate completes the synthesis. 16.32 ( a ) A reasonable mechanism is one that parallels the usual one for acid-catalyzed ether formation from alcohols, modi fi ed to accommodate these particular starting materials and products. Begin with protonation of one of the oxygen atoms of ethylene glycol. The protonated alcohol then reacts in the usual way with another molecule of alcohol to give
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