Question

For the $S_{N}1$ solvolysis of 5-bromopent-2-ene in ethanol, which of the following is true?

• A. The reaction is an example of ethanolysis
• B. The reaction proceeds via a resonance-stabilized carbocation
• C. The reaction gives a mixture or products
• D. There is a single, distinct major product

Answer 1

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

There is a single, distinct major product

Once we evaluate the intermediate, the product becomes obvious.

No primary carbocation has been shown. This is because it readily rearranges to a more stable carbocation (shown above). The only product is: