Ring closure occurs by an intramolecular Williamson reaction.Dehydrohalogenation of compound C converts it to the fnal product, D.The alternative series of events, in which double-bond formation proceeds ring closure, isunlikely, 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 frst 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
This is the end of the preview. Sign up
access the rest of the document.
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.