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JEE Advanced 2026 · Paper 2, Chemistry question 18

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Question Stem for Question Nos. 17 and 18

Consider the following reaction sequence in which J, K, L and M are the major products.

Given:
Atomic mass (in amu): H : 1, C : 12, N : 14, O : 16, S : 32, Br : 80, Ba : 137

m-Xylene with (1) ClCOCH₂Cl, anhyd. AlCl₃; (2) NaI, heat; (3) sodium 3-nitrophenoxide gives J. J with (1) NaBH₄, (2) PBr₃ gives K (molar mass 350 g/mol). K with NH₃ (excess) gives L (a nitrogen-containing compound); K with PhSNa gives M (a sulphur-containing compound).

In sulphur estimation by Carius method, the amount of BaSOX4\ce{BaSO4} formed from 3.79 g of M is ____ g.

Answer and worked solution

Official answer: 2.33

M. PhSX−\ce{PhS-} substitutes Br in K: ArCH(SPh)CHX2OArX′\ce{ArCH(SPh)CH2OAr'}, CX22HX21NOX3S\ce{C22H21NO3S}, with M=350−80+109=379M=350-80+109=379. It contains one S.

Carius. 3.79/379=0.0103.79/379=0.010 mol of M gives 0.010 mol BaSOX4\ce{BaSO4}:
0.010×233=2.33 g.0.010\times233=2.33\text{ g}.

Topics:Qualitative and quantitative analysis of organic compoundsSN1 and SN2
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