Question

Identify A and B in the chemical reaction. p-Nitrotoluene $\xrightarrow{Cl_2, h\nu}$ A $\xrightarrow{NaI, dry acetone}$ B

• A. A
• B. B
• C. C
• D. D

Hint:

Remember: $Cl_2/h\nu$ targets the aliphatic side chain (benzylic position), whereas $Cl_2/FeCl_3$ would target the aromatic ring.

Answer 1

The Correct Option is A

Step 1: Reaction of p-nitrotoluene with $Cl_2/h\nu$ (side-chain chlorination) results in the substitution of a hydrogen on the methyl group. This forms p-nitrobenzyl chloride (A).
Step 2: Reaction of A with $NaI$ in dry acetone is the Finkelstein reaction.
Step 3: The chloride is substituted by iodide to form p-nitrobenzyl iodide (B).