Problem

Identify the compound in each of the following pairs that reacts at the faster rate in an...

Identify the compound in each of the following pairs that reacts at the faster rate in an SN1 reaction:

(a) Isopropyl bromide or isobutyl bromide


(b) Cyclopentyl iodide or 1-methylcyclopentyl iodide


(c) Cyclopentyl bromide or 1-bromo-2,2-dimethylpropane


(d) tert-Butyl chloride or tert-butyl iodide

Sample Solution (a) Isopropyl bromide, (CH3)2CHBr, is a secondary alkyl halide, whereas isobutyl bromide, (CH3)2CHCH2Br, is primary. Because the rate-determining step in an SN1 reaction is carbocation formation and secondary carbocations are more stable than primary ones, isopropyl bromide is more reactive than isobutyl bromide in nucleophilic substitution by the SN1 mechanism.

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