JEE MainChemistryAmines
A neutral aromatic compound 'A' undergoes the following sequence of reactions: A (i) Sn, HCl (ii) Br ₂ (aq) (iii) NaNO ₂ , HCl, 273 K (iv) C ₂ H ₅ OH 1,3,5-tribromobenzene + compound 'B' Identify compounds 'A' and 'B'.
Options
- ANitrobenzene and ethanoic acid
- BAniline and ethanal
- CNitrobenzene and ethanal
- DNitrobenzene and phenol
Correct answer
C. Nitrobenzene and ethanal
Step-by-step solution
Working backwards from the final products: The formation of 1,3,5-tribromobenzene via reaction with C ₂ H ₅ OH implies a deamination step. The intermediate must be 2,4,6-tribromobenzenediazonium chloride. During this deamination, ethanol acts as a mild reducing agent and is itself oxidized to ethanal ( CH ₃ CHO ). Thus, compound 'B' is ethanal. The diazonium salt is formed from 2,4,6-tribromoaniline, which in turn is produced by the exhaustive aqueous bromination of aniline. Aniline is formed by the reduction of co