Dolbier HW Solutions 246

Dolbier HW - 240 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS(c Nucleophilic substitution by cyanide converts the allylic bromide to

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( 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 E2 elimination. ( e ) Cyclopentadiene formed in part ( d ) is needed in order to form the required Diels Alder adduct. 10.24 The 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 addition to 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.

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