Identify the compound in each of the following pairs that reacts with sodium iodide in acetone at the faster rate:
(a) 1-Chlorohexane or cyclohexyl chloride
(b) 1-Bromopentane or 3-bromopentane
(c) 2-Chloropentane or 2-fluoropentane
(d) 2-Bromo-2-methylhexane or 2-bromo-5-methylhexane
(e) 2-Bromopropane or 1-bromodecane
Sample Solution (a) Compare the structures of the two chlorides. 1-Chlorohexane is a primary alkyl chloride; cyclohexyl chloride is secondary. Primary alkyl halides are less crowded at the site of substitution than secondary ones and react faster in substitution by the SN2 mechanism. 1-Chlorohexane is more reactive.
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