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JEE Advanced 2026Paper 2
Exam
JEE Advanced
Year
2026
Paper
Paper 2
Subject
Chemistry
Chapter
Amines

JEE Advanced 2026 · Paper 2 · Chemistry · Amines

Passage: Consider the following reaction sequence in which J , K ,...

Passage: Consider the following reaction sequence in which J\textbf{J}, K\textbf{K}, L\textbf{L} and M\textbf{M} are the major products.
Passage: Consider the following reaction sequence in which J , K , L and M are the major products. Given: Atomic mass
Given:
Atomic mass (in amu): H : 11, C : 1212, N : 1414, O : 1616, S : 3232, Br : 8080, Ba : 137137

Question: The volume of 11 M aqueous H2SO4\text{H}_2\text{SO}_4 required to completely neutralize the ammonia evolved from 5.725.72 g of L\textbf{L} in Kjeldahl's method of nitrogen estimation is ____ mL.

Correct answer

0

Step-by-step solution

The reaction sequence proceeds as follows:

1. Friedel-Crafts Acylation: Reaction of mm-xylene (1,3-dimethylbenzene) with chloroacetyl chloride (ClCH2COCl\text{ClCH}_2\text{COCl}) in the presence of anhydrous AlCl3\text{AlCl}_3 occurs at the less sterically hindered activated position (position 4) to give 1-(2,4-dimethylphenyl)-2-chloroethan-1-one.

2. Finkelstein Reaction: Heating with NaI\text{NaI} replaces the chloride with iodide, yielding 1-(2,4-dimethylphenyl)-2-iodoethan-1-one.

3. Williamson Ether Synthesis: Reaction with sodium 3-nitrophenoxide gives compound J\textbf{J}, which is 1-(2,4-dimethylphenyl)-2-(3-nitrophenoxy)ethan-1-one.

4. Reduction and Bromination: NaBH4\text{NaBH}_4 reduces the ketone group in J\textbf{J} to a secondary alcohol without affecting the nitro group. Subsequent reaction with PBr3\text{PBr}_3 converts the alcohol to a bromide, yielding compound K\textbf{K}, 1-(1-bromo-2-(3-nitrophenoxy)ethyl)-2,4-dimethylbenzene.
The molecular formula of K\textbf{K} is C16H16BrNO3\text{C}_{16}\text{H}_{16}\text{BrNO}_3.
Molar mass of K=(16×12)+(16×1)+80+14+(3×16)=192+16+80+14+48=350 g/mol\textbf{K} = (16 \times 12) + (16 \times 1) + 80 + 14 + (3 \times 16) = 192 + 16 + 80 + 14 + 48 = 350 \text{ g/mol}, which matches the given data.

5. Amination: Reaction of K\textbf{K} with excess NH3\text{NH}_3 results in nucleophilic substitution of the bromide to form a primary amine, compound L\textbf{L}, 1-(2,4-dimethylphenyl)-2-(3-nitrophenoxy)ethanamine.
The molecular formula of L\textbf{L} is C16H18N2O3\text{C}_{16}\text{H}_{18}\text{N}_2\text{O}_3.
Molar mass of L=(16×12)+(18×1)+(2×14)+(3×16)=192+18+28+48=286 g/mol\textbf{L} = (16 \times 12) + (18 \times 1) + (2 \times 14) + (3 \times 16) = 192 + 18 + 28 + 48 = 286 \text{ g/mol}.

Moles of L\textbf{L} taken = 5.72 g286 g/mol=0.02 mol\dfrac{5.72 \text{ g}}{286 \text{ g/mol}} = 0.02 \text{ mol}.

In Kjeldahl's method, nitrogen present in nitro (−NO2-\text{NO}_2) groups is not converted to ammonium sulfate and thus is not estimated. Only the nitrogen from the primary amine (−NH2-\text{NH}_2) group will evolve as ammonia (NH3\text{NH}_3).
Therefore, 1 mole of L\textbf{L} yields 1 mole of NH3\text{NH}_3.
Moles of NH3\text{NH}_3 evolved = 0.02 mol0.02 \text{ mol}.

The neutralization reaction with sulfuric acid is:
2NH3+H2SO4→(NH4)2SO42\text{NH}_3 + \text{H}_2\text{SO}_4 \rightarrow (\text{NH}_4)_2\text{SO}_4

Moles of H2SO4\text{H}_2\text{SO}_4 required = 0.022=0.01 mol\dfrac{0.02}{2} = 0.01 \text{ mol}.

Given the molarity of H2SO4\text{H}_2\text{SO}_4 is 1 M1 \text{ M}:
Volume of H2SO4=MolesMolarity=0.01 mol1 mol/L=0.01 L=10 mL\text{H}_2\text{SO}_4 = \dfrac{\text{Moles}}{\text{Molarity}} = \dfrac{0.01 \text{ mol}}{1 \text{ mol/L}} = 0.01 \text{ L} = 10 \text{ mL}.

Answer: 1010
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