Consider the rigorous execution of the Sandmeyer reaction for the targeted synthesis of bromobenzene — Haloalkanes and Haloarenes Chemistry Question
Question
Consider the rigorous execution of the Sandmeyer reaction for the targeted synthesis of bromobenzene from aniline. Which of the following statements accurately reflect the required environmental conditions, reagents, and mechanistic observations?
💡 Solution & Explanation
A) True. Aliphatic diazonium salts decompose instantly, while aromatic ones are barely stable only at $0-5^\circ C$ due to resonance. Above this, they hydrolyze to phenol. B) True. The Sandmeyer reaction for bromides mandates matching the cuprous salt with its corresponding acid ($CuBr$ in $HBr$) to avoid halogen swapping. C) True. The evolution of $N_2$, one of the most stable molecules known, provides massive entropic and enthalpic driving force. D) False. As discussed, the Sandmeyer reaction is established to proceed via an aryl radical mechanism initiated by copper, not an $S_N1$ phenyl cation.