Identify the correct pair of starting material and reagent that yields 1-bromo-4-(isocyanomethyl)benzene as the major organic product.

Step-by-step solution

The product is 1-bromo-4-(isocyanomethyl)benzene, which contains an isocyanide (-NC) group attached to a methyl carbon, and a bromine atom on the benzene ring. To form an isocyanide (-NC) as the major product, the nucleophilic substitution must be carried out using AgCN. AgCN is predominantly covalent, making the nitrogen lone pair available for attack. In contrast, KCN is ionic and leads to the formation of cyanides (-CN). The starting material must have a leaving group (such as -Cl) on the methyl carbon to underg