Question

$S_{N}1$ solvolysis of 4-bromopent-2-ene in ethanol gives:

• A. 4-methoxypent-2-ene
• B. The same product as obtained during $S_{N}1$ solovolysis of 5-bromopent-2-ene in ethanol
• C. The reaction gives a mixture or products
• D. The reaction proceeds via a resonance-stabilized carbocation

Answer 1

Answer: (A), (B), (D)

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: