The compound that will undergo SN1 reaction with the fastest rate is
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Answer
(4) [figure]
Solution
Rate of SN1 depends on the stability of the carbocation formed in the slow step.
(1) Cyclohexylmethyl bromide → 1 carbocation (least stable).
(2) Bromocyclohexane → 2 carbocation.
(3) Bromobenzene: C–Br has partial double-bond character and the phenyl cation is very unstable → no SN1.
(4) 1-Bromo-1-phenylethane → 2 benzylic carbocation C6H5 +CHCH3, stabilised by resonance with the ring (most stable).
(4) reacts fastest.
Answer: (4)