(c)Nucleophilic substitution by cyanide converts the allylic bromide to 3-cyanocyclopentene.(d)Reaction of the allylic bromide with a strong base will yield cyclopentadiene by an E2elimination.(e)Cyclopentadiene formed in part (d) is needed in order to form the required Diels–Alderadduct.10.24The starting material in all cases is 2,3-dimethyl-1,3-butadiene.(a)Hydrogenation of both double bonds will occur to yield 2,3-dimethylbutane.(b)Direct addition of 1 mol of hydrogen chloride will give the product of Markovnikov additionto one of the double bonds, 3-chloro-2,3-dimethyl-1-butene.
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This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.