JEE Main Chemistry: Halogens and Arenes questions with solutions

Q1. When p-nitrotoluene undergoes further nitration, the principal product formed is:

1. 2,4-dinitrotoluene
2. 2,6-dinitrotoluene
3. p-nitrobenzyl alcohol with nitro substitution
4. 2,4,6-trinitrotoluene

Answer: 2,4-dinitrotoluene

In p-nitrotoluene (1-methyl-4-nitrobenzene), the CH3 group activates ortho (C-2, C-6) and para (C-4, occupied). The NO2 group deactivates but directs meta to itself — meta to C-4 means C-1 (occupied) and C-2, C-6 (same positions). C-2 is activated by both effects (ortho to CH3 and meta to NO2), making it the preferred site. The product is 2,4-dinitrotoluene.