Dolbier HW Solutions 202

Dolbier HW Solutions 202 - 196 NUCLEOPHILIC...

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( h ) The unimolecular mechanisms S N 1 and E1 involve the formation of carbocation intermediates. ( i ) Rearrangements are possible when carbocations are intermediates in a reaction. Thus reac- tions occurring by the S N 1 and E1 mechanisms are most likely to have a rearranged carbon skeleton. ( j ) Iodide is a better leaving group than bromide, and alkyl iodides will react faster than alkyl bromides by any of the four mechanisms S N 1, S N 2, E1, and E2. 8.30 ( a ) Cyclopentyl cyanide can be prepared from a cyclopentyl halide by a nucleophilic substitution reaction. The f rst task, therefore, is to convert cyclopentane to a cyclopentyl halide. An analogous sequence involving cyclopentyl bromide could be used. ( b ) Cyclopentene can serve as a precursor to a cyclopentyl halide. Once cyclopentyl bromide has been prepared, it is converted to cyclopentyl cyanide by nucleophilic substitution, as shown in part ( a ). ( c ) Reaction of cyclopentanol with hydrogen bromide gives cyclopentyl bromide. Then
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