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Among the following compounds I-IV, which one forms a yellow precipitate on reacting sequentially with (i) NaOH (ii) dil. HNO3 (iii) AgNO3? I: p-chlorotoluene II: m-chlorotoluene III: o-bromotoluene IV: o-chlorobenzyl iodide

1. II
2. IV
3. I
4. III

Correct answer: IV

Solution

The correct option is IV because o-chlorobenzyl iodide can undergo a nucleophilic substitution reaction with NaOH to form a phenolic compound, which upon treatment with dilute HNO3 can be oxidized to a corresponding phenol. This phenol then reacts with AgNO3 to form a yellow precipitate of silver halide, indicating the presence of the halogen.

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