NEET 2022 · ChemistryPrevious Year Question

Which of the following sequence of reagents is suitable to synthesize chlorobenzene from the starting material shown?

Answer: (A) (A) Benzene, $Cl X_{2}$ , anhydrous $FeCl X_{3}$ . Direct electrophilic aromatic halogenation gives chlorobenzene: $\ce{C6H6 + Cl2 ->[\text{anhyd.$

A.(A) Benzene, $Cl X_{2}$ , anhydrous $FeCl X_{3}$ ✓
B.(B) Phenol, $NaNO X_{2}$ , $HCl$ , $CuCl$
C.(C) Aniline $(C X_{6} H X_{5} NH X_{2})$ , $HCl$
D.(D) Aniline $(C X_{6} H X_{5} NH X_{2})$ , $HCl$ , heating

Correct Answer

(A) (A) Benzene, $Cl X_{2}$ , anhydrous $FeCl X_{3}$

Solution & Explanation

Direct electrophilic aromatic halogenation gives chlorobenzene: $C X_{6} H X_{6} + Cl X_{2} anhyd. FeCl X_{3} C X_{6} H X_{5} Cl + HCl$ . The Lewis acid $FeCl X_{3}$ generates the electrophile $Cl X^{+}$ . Option B starts from phenol (no $- NH X_{2}$ to diazotise, so no diazonium forms); options C/D give a diazonium/anilinium but lack $CuCl$ , so they cannot deliver $Cl$ to the ring.

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