Fundamentals of Organic ChemistryChemistryAmines
Identify the major product formed in the following reaction sequence.
Correct answer
2
Step-by-step solution
Electrophilic aromatic bromination of nitrobenzene occurs at the meta position due to the meta-directing nature of the -NO₂ group, yielding m-bromonitrobenzene. Catalytic hydrogenation using H₂/Ni reduces the -NO₂ group to an -NH₂ group, forming m-bromoaniline. Diazotization with NaNO₂ and H^+ converts the amine into a diazonium salt. The Sandmeyer reaction with CuCN replaces the diazonium group with a cyanide group, producing m-bromobenzonitrile. Reduction of the nitrile group with LiAlH₄ followed by hydrolysis yi