Predict the major product for the following reaction.

Question

Quizplus · Accepted Answer

The reaction follows an SN2 mechanism, where the nucleophile attacks the electrophilic carbon directly. In the first step, the bromine is displaced by the strong nucleophile, cyanide ion. This results in the formation of an intermediate where the negative charge is located on the carbon bearing the leaving group.

This intermediate is unstable and rearranges to a more stable isomer where the negative charge is on the adjacent carbon. This rearrangement is facilitated by the presence of the phenyl group which stabilizes the negative charge.

Finally, the remaining proton is lost to form the product. Since the rearranged intermediate is more stable, the major product is predicted to be II.

Predict the Major Product for the Following Reaction