# Can an SN1 reaction occur in compounds with the leaving group attached to a primary carbon, which can later rearrange?

Can SN1 reactions occur in compounds where the carbocation, even though is is initially $1^\circ$, can rearrange to form a more stable carbocation?

Examples cases:

• Under typical lab conditions a primary carbocation is not likely to form unless there is stabilization by an adjacent double bond or benzene ring, or unless there is a neighboring group that can provide neighboring group stabilization - but then we really don't have a simple primary carbocation in such cases. BTW, in your first example, a H shift would produce an antiaromatic (4n electrons) cyclopentadienyl cation, so this won't occur. – ron Sep 18 '16 at 15:01
• Well, a benzyl cation is technically a primary one, so … – Jan Sep 19 '16 at 13:03
• Fairly sure neopentyl iodide reacts with aqueous Ag+ to give the rearranged product t-amyl alcohol – orthocresol Sep 20 '16 at 17:16
• @ron Do you mind posting an answer? Thanks! – Gaurang Tandon Mar 28 '18 at 13:15