Which one of the following is the best synthesis for 3,5-dibromotoluene? A) toluene, Br₂/FeBr₃ excess B) 1. p-toluidine, Br₂/ FeBr₃; 2) NaNO₂/HCl,

Question

Which one of the following is the best synthesis for 3,5-dibromotoluene? A) toluene, Br₂/FeBr₃ excess B) 1. p-toluidine, Br₂/ FeBr₃; 2) NaNO₂/HCl, < 5°C 3) H₃PO₂ C) 1. Toluene, HNO₃/H₂SO₄ 2) NH₃ 3) NaNO₂/HCl, < 5°C 4) CuBr D) m-dibromobenzene, CH₃Cl/AlCl₃ E) 1. m-bromotoluene, HNO₃, H₂SO₄ 2) Fe/HCl 3) NaNO₂/HCl, < 5°C 4) CuBr

Quizplus · Accepted Answer

Option B involves the selective bromination of p-toluidine to form 3-bromo-4-methyl aniline, which is then diazotized and coupled with HBr to give the desired 3,5-dibromotoluene. The other options either involve multiple steps or are not selective enough in their bromination reactions.

Which One of the Following Is the Best Synthesis for 3,5-Dibromotoluene