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Practical Organic Chemistry question

2022 · Shift 1 · Q7
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Practical Organic Chemistry question

2022 · Shift 1 · Q7

JEE AdvancedChemistryPractical Organic ChemistryNumerical+3 / −1
The weight percentage of hydrogen in Q\mathbf{Q}Q, formed in the following reaction sequence, is ‾\underline{\hspace{2cm}}​. JEE Advanced 2022 Paper 1 Online Chemistry - Practical Organic Chemistry Question 3 English [Given: Atomic mass of H=1,C=12, N=14,O=16, S=32,Cl=35\mathrm{H}=1, \mathrm{C}=12, \mathrm{~N}=14, \mathrm{O}=16, \mathrm{~S}=32, \mathrm{Cl}=35H=1,C=12, N=14,O=16, S=32,Cl=35 ]
Numerical answer
View written solutionFree

Correct answer: 1.30TO1.32

  1. Identify the reaction sequence from the practical organic chemistry context

    In this standard sequence:

    • Aniline is first diazotised to benzene diazonium chloride.
    • On treatment with sulfurous acid / sulfur dioxide in presence of copper salts, the diazonium salt gives benzenesulfonyl chloride.
    • Benzenesulfonyl chloride then reacts with aniline to form the sulfonamide derivative used in the Hinsberg-type reaction sequence.

    Thus, QQQ is N-phenyl benzenesulfonamide.

  2. Write the molecular formula of QQQ

    Benzenesulfonyl chloride has formula: C6H5SO2ClC_6H_5SO_2ClC6​H5​SO2​Cl

    Reaction with aniline C6H5NH2C_6H_5NH_2C6​H5​NH2​ replaces Cl by NH(C6H5)NH(C_6H_5)NH(C6​H5​): C6H5SO2Cl+C6H5NH2→C6H5SO2NHC6H5+HClC_6H_5SO_2Cl + C_6H_5NH_2 \rightarrow C_6H_5SO_2NHC_6H_5 + HClC6​H5​SO2​Cl+C6​H5​NH2​→C6​H5​SO2​NHC6​H5​+HCl

    Therefore, Q=C12H11NO2SQ = C_{12}H_{11}NO_2SQ=C12​H11​NO2​S

  3. Calculate molar mass of QQQ

    M=12(12)+11(1)+14+2(16)+32M = 12(12) + 11(1) + 14 + 2(16) + 32M=12(12)+11(1)+14+2(16)+32 =144+11+14+32+32= 144 + 11 + 14 + 32 + 32=144+11+14+32+32 =233= 233=233

  4. Calculate percentage of hydrogen

    Mass of hydrogen in one mole of QQQ: =11= 11=11

    Hence, %H=11233×100\%H = \frac{11}{233} \times 100%H=23311​×100

    %H=4.72% (approximately)\%H = 4.72\% \text{ (approximately)}%H=4.72% (approximately)

  5. Compare with stored answer

    The derived value is: 4.724.724.72

    The stored correct answer is 1.301.301.30 to 1.321.321.32, which does not match.

    So the stored answer appears inconsistent with the standard reaction/product interpretation.

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