SN1 solvolysis of 4-bromopent-2-ene in ethanol gives:
4-methoxypent-2-ene
The same product as obtained during SN1 solovolysis of 5-bromopent-2-ene in ethanol
The reaction proceeds via a resonance-stabilized carbocation
Once we evaluate the intermediate, the product becomes obvious.
Although not shown, the intermediate does have resonance contributors – both of which are equivalent. The only product is: