# Rearrangement considerations in feasibility of SN1 in given reactants

I have been asked to compare the feasibility of Unimolecular Nucleophilic Substitution ($$\mathrm{S_N1}$$) in the following question.

I have received instruction that the reaction will be feasible only in the first compound (which results in a 3° stable carbocation) since 1-chloro-1-methylcyclopropane is angle strained and the resulting carbocation in this case will be unstable.

However, if we consider the possibility of hydride rearrangement in the second molecule, after formation of the carbocation, the following rearrangement should stabilise the carbocation formed, through the delocalisation of sigma electron pair as is seen in the case of cyclopropyl methyl carbocations.

Where exactly am I going wrong?