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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx126

The best two-step route to 1-chloro-3-nitrobenzene starting from benzene is

A $Cl X_{2}$ in sunlight first, then $HNO X_{3}$ /conc. $H X_{2} SO X_{4}$
B $HNO X_{3}$ /conc. $H X_{2} SO X_{4}$ first, then $Cl X_{2}$ in sunlight
C $Cl X_{2}$ with $FeCl X_{3}$ first, then $HNO X_{3}$ /conc. $H X_{2} SO X_{4}$
D $HNO X_{3}$ /conc. $H X_{2} SO X_{4}$ first, then $Cl X_{2}$ with $FeCl X_{3}$

Answer: D

The

NO X_{2}

group is a meta director, so nitration must come first; chlorination of nitrobenzene with

Cl X_{2} / FeCl X_{3}

then places

Cl

meta to

NO X_{2}

. If chlorination came first, the ortho/para directing

Cl

would give 1-chloro-2-nitro and 1-chloro-4-nitrobenzene. Sunlight causes radical addition giving

C X_{6} H X_{6} Cl X_{6}

.

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