Carbocation Rearrangements in SN1 reactions

[![](https://i.stack.imgur.com/gE1Di.png "source: imgur.com")](https://i.stack.imgur.com/9lQFg.jpg)


Would one get 1-(1-chloroethyl)-1-methylcyclobutane?


I am not sure if the driving force identification is correct? Is my going from a 2° to a 3° carbocation correct? Does anyone have any tips for knowing when to look out for rearrangements?


[![](https://i.stack.imgur.com/dk7RW.png "source: imgur.com")](https://i.stack.imgur.com/Ezxym.jpg)




I think the solvolysis would involve rearrangement to the cyclopentyl carbocation as indicated in the figure below. The driving force for the rearrangement is two-fold


1. without rearrangement, the cyclobutyl compound would generate a secondary carbocation; with rearrangement a more stable tertiary carbocation is generated instead
2. release of strain as the 4-membered ring opens to a 5-membered ring


![enter image description here](https://i.stack.imgur.com/deoW8.jpg)


The tertiary cyclopentyl carbocation ultimately captures a solvent molecule as indicated.


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