The aromatic amine shown is diazotised at 0-5 $^{\circ}$ C, the product is treated with $CuCN$ / $KCN$ , and the resulting compound is reduced with $LiAlH X_{4}$ . Which structure is the final product?

Answer: A

The compound shown is 4-bromoaniline. Diazotisation and the Sandmeyer cyanation give 4-bromobenzonitrile (the aryl bromide is untouched).

LiAlH X_{4}

reduces the nitrile to a primary amine,

- CH X_{2} NH X_{2}

, giving 4-bromobenzylamine; the amine now has one more carbon than the starting aniline.