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Compounds Containing Nitrogen question

2024 · 8 Apr · Shift 2 · Q3
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Compounds Containing Nitrogen question

2024 · 8 Apr · Shift 2 · Q3

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Given below are two statements : Statement (I) : All the following compounds react with p-toluenesulfonyl chloride. C6H5NH2(C6H5)2NH(C6H5)3N\mathrm{C}_6 \mathrm{H}_5 \mathrm{NH}_2 \quad\left(\mathrm{C}_6 \mathrm{H}_5\right)_2 \mathrm{NH} \quad\left(\mathrm{C}_6 \mathrm{H}_5\right)_3 \mathrm{N}C6​H5​NH2​(C6​H5​)2​NH(C6​H5​)3​N Statement (II) : Their products in the above reaction are soluble is aqueous NaOH\mathrm{NaOH}NaOH. In the light of the above statements, choose the correct answer from the options given below :
  1. A
    Statement I is false but Statement II is true
  2. B
    Both Statement I and Statement II are true
  3. C
    Both Statement I and Statement II are false
  4. D
    Statement I is true but Statement II is false
View written solutionFree

Correct answer: C

  1. Identify the reaction involved

    ppp-Toluenesulfonyl chloride reacts with amines in the Hinsberg test.

    General behavior:

    • Primary amines react to form sulfonamides having an acidic N−H\mathrm{N-H}N−H proton, so they are soluble in aqueous NaOH.
    • Secondary amines react to form sulfonamides with no acidic hydrogen on nitrogen, so they are insoluble in aqueous NaOH.
    • Tertiary amines generally do not react with sulfonyl chloride because there is no N−H\mathrm{N-H}N−H proton required for sulfonamide formation.
  2. Examine Statement (I)

    The compounds given are:

    • C6H5NH2\mathrm{C_6H_5NH_2}C6​H5​NH2​ = aniline = primary amine
    • (C6H5)2NH\left(\mathrm{C_6H_5}\right)_2\mathrm{NH}(C6​H5​)2​NH = diphenylamine = secondary amine
    • (C6H5)3N\left(\mathrm{C_6H_5}\right)_3\mathrm{N}(C6​H5​)3​N = triphenylamine = tertiary amine

    Now check reactivity with ppp-toluenesulfonyl chloride:

    • Aniline: reacts
    • Diphenylamine: reacts
    • Triphenylamine: does not react

    Therefore, the statement "All the following compounds react with ppp-toluenesulfonyl chloride" is false.

    So, Statement (I) is false.

  3. Examine Statement (II)

    Statement (II): "Their products in the above reaction are soluble in aqueous NaOH\mathrm{NaOH}NaOH."

    Check product solubility:

    • Product from aniline (primary amine) is a sulfonamide containing acidic N−H\mathrm{N-H}N−H, hence soluble in aqueous NaOH.
    • Product from diphenylamine (secondary amine) is an N,NN,NN,N-disubstituted sulfonamide with no acidic hydrogen, hence insoluble in aqueous NaOH.
    • Triphenylamine does not react, so no such product forms.

    Hence it is incorrect to say that the products are soluble in aqueous NaOH\mathrm{NaOH}NaOH.

    So, Statement (II) is also false.

  4. Conclusion

    • Statement (I): False
    • Statement (II): False

    Therefore, the correct option is: C: Both Statement I and Statement II are false\boxed{\text{C: Both Statement I and Statement II are false}}C: Both Statement I and Statement II are false​

  5. Comparison with stored answer

    Stored correct answer = C.

    My derived answer also = C. Hence, they agree.

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