Solution
Core Logic
- When bromobenzene reacts with concentrated HNO₃ (nitration), the bromine atom is ortho/para directing. However, under drastic conditions with excess concentrated nitrating mixture, 1-bromo-2,4,6-trinitrobenzene is formed (Compound A).
- When 1-bromo-2,4,6-trinitrobenzene (Compound A) is treated with NaOH, the presence of three strong electron-withdrawing -NO₂ groups activates the aromatic ring toward Nucleophilic Aromatic Substitution (SNAr). The -Br is easily replaced by -OH to form 2,4,6-trinitrophenol (picric acid).
- Subsequent acidification with HCl yields the neutral picric acid (Compound B).
Pattern Recognition
Multiple NO₂ groups drastically increase the susceptibility of halobenzenes to SNAr. Bromine is replaced completely by OH^- under alkaline conditions.
Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes Class 12 Chemistry: Alcohols, Phenols and Ethers