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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc109

Nitrobenzene is brominated with $Br X_{2} / FeBr X_{3}$ to give Y, and Y is reduced with $Sn / HCl$ to give Z. Select the correct statements.

Adiazotisation of Z followed by $H X_{3} PO X_{2}$ gives 1,3-dibromobenzene
BY is 1-bromo-3-nitrobenzene
CZ is 3-bromoaniline
DZ gives a positive carbylamine test

Answer: B, C, D

The nitro group directs bromine meta, so Y = 1-bromo-3-nitrobenzene and Z = 3-bromoaniline, a primary aromatic amine that gives the carbylamine test. Diazotisation then

H X_{3} PO X_{2}

removes the nitrogen, giving bromobenzene, not 1,3-dibromobenzene (that would need

CuBr / HBr

).

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