4-Methylaniline is subjected to: (i) $(CH X_{3} CO) X_{2} O$ / pyridine; (ii) $HNO X_{3} + H X_{2} SO X_{4}$ at low temperature (mononitration); (iii) aqueous $NaOH$ , heat (hydrolysis); (iv) $NaNO X_{2}$ / dil. $HCl$ , 273-278 K; (v) $H X_{3} PO X_{2}$ . The major final product is

Answer: A

The acetamido group (stronger director) places

NO X_{2}

ortho to itself, i.e. at position 2 of 4-methylacetanilide, which is meta to

CH X_{3}

. Hydrolysis gives 4-methyl-2-nitroaniline; diazotisation and

H X_{3} PO X_{2}

remove the nitrogen, leaving

CH X_{3}

and

NO X_{2}

in a 1,3-relationship: 3-nitrotoluene.