Dolbier HW Solutions 324

Dolbier HW Solutions 324 - 418 ETHERS, EPOXIDES, AND...

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Ring closure occurs by an intramolecular Williamson reaction. Dehydrohalogenation of compound C converts it to the f nal product, D. The alternative series of events, in which double-bond formation proceeds ring closure, is unlikely, because it requires nucleophilic attack by the alkoxide on a vinyl bromide. ( b ) Lithium aluminum hydride reduces the carboxylic acid to the corresponding primary alcohol, compound E. Treatment of the vicinal chlorohydrin with base results in formation of an epox- ide, compound F. As actually carried out, the f rst step proceeded in 56 58% yield, the second step in 65 70% yield. ( c ) Treatment of the vicinal chlorohydrin with base results in ring closure to form an epoxide (compound G). Recall that attack occurs on the side opposite that of the carbon
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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