JEE Advanced · 2014 · 25 May 2014 · Paper 2 · Hydrocarbons

Match the four starting materials (P, Q, R, S) given in List I with the corresponding reaction schemes (I, II, III, IV) provided in List II and select the correct answer using the code given below the lists.

List-I

P. (see structure)

Q. (see structure)

R. (see structure)

S. (see structure)

List-II

1. Scheme I: (i) ${\mathrm{KMnO}}_4,\mathrm{HO}$, heat (ii) ${\mathrm{H}}^{\oplus },{\mathrm{H}}_2\mathrm{O}$ (iii) ${\mathrm{SOCl}}_2$ (iv) ${\mathrm{NH}}_3$ → ${\mathrm{C}}_7{\mathrm{H}}_6{\mathrm{N}}_2{\mathrm{O}}_3$

1. Scheme II: (i) $\mathrm{Sn}/\mathrm{HCl}$ (ii) ${\mathrm{CH}}_3\mathrm{COCl}$ (iii) conc. ${\mathrm{H}}_2{\mathrm{SO}}_4$ (iv) ${\mathrm{HNO}}_3$ (v) dil. ${\mathrm{H}}_2{\mathrm{SO}}_4$, heat (vi) HO → ${\mathrm{C}}_6{\mathrm{H}}_6{\mathrm{N}}_2{\mathrm{O}}_2$

1. Scheme III: (i) red hot iron, 873 K (ii) fuming ${\mathrm{HNO}}_3,{\mathrm{H}}_2{\mathrm{SO}}_4$, heat (iii) ${\mathrm{H}}_2\mathrm{S}.{\mathrm{NH}}_3$ (iv) ${\mathrm{NaNO}}_2,{\mathrm{H}}_2{\mathrm{SO}}_4$ (v) hydrolysis → ${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{NO}}_3$

1. Scheme IV: (i) conc. ${\mathrm{H}}_2{\mathrm{SO}}_4,60^{\circ }\mathrm{C}$ (ii) conc. ${\mathrm{HNO}}_3$, conc. ${\mathrm{H}}_2{\mathrm{SO}}_4$ (iii) dil. ${\mathrm{H}}_2{\mathrm{SO}}_4$, heat → ${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{NO}}_4$

Codes: