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Compounds Containing Nitrogen question

2021 · 18 Mar · Shift 2 · Q11
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Compounds Containing Nitrogen question

2021 · 18 Mar · Shift 2 · Q11

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
An organic compound "A" on treatment with benzene sulphonyl chloride gives compound B. B is soluble in dil. NaOH solution. Compound A is :
  1. A
    JEE Main 2021 (Online) 18th March Evening Shift Chemistry - Compounds Containing Nitrogen Question 143 English Option 1
  2. B
    C6H5C_6H_5C6​H5​ −-− NHCH2CH3NHCH_2CH_3NHCH2​CH3​
  3. C
    C6H5C_6H_5C6​H5​ −-− N −-− (CH3)2(CH_3)_2(CH3​)2​
  4. D
    C6H5C_6H_5C6​H5​ −-− CH2NHCH3CH_2NHCH_3CH2​NHCH3​
View written solutionFree

Correct answer: A

  1. Identify the reaction involved

    Treatment with benzene sulphonyl chloride is the Hinsberg test for amines.

    Reagent: C6H5SO2ClC_6H_5SO_2ClC6​H5​SO2​Cl

  2. Recall Hinsberg test results

    • Primary amine (1∘)(1^\circ)(1∘): forms sulphonamide having an acidic N−HN-HN−H proton, so it is soluble in dilute NaOH.
    • Secondary amine (2∘)(2^\circ)(2∘): forms sulphonamide with no acidic hydrogen on nitrogen, so it is insoluble in dilute NaOH.
    • Tertiary amine (3∘)(3^\circ)(3∘): does not form sulphonamide in the usual way.

    Since compound BBB is soluble in dilute NaOH, compound AAA must be a primary amine.

  3. Check the options

    • Option B: C6H5−NHCH2CH3C_6H_5-NHCH_2CH_3C6​H5​−NHCH2​CH3​

      Nitrogen is attached to phenyl and ethyl groups, and has one H. So this is a secondary amine.

    • Option C: C6H5−N(CH3)2C_6H_5-N(CH_3)_2C6​H5​−N(CH3​)2​

      Nitrogen is attached to phenyl and two methyl groups. So this is a tertiary amine.

    • Option D: C6H5CH2NHCH3C_6H_5CH_2NHCH_3C6​H5​CH2​NHCH3​

      Nitrogen is attached to benzyl and methyl groups, and has one H. So this is a secondary amine.

    Therefore, the only suitable choice must be Option A, which is the primary amine among the options.

  4. Conclusion

    Since only a primary amine gives a benzene sulphonyl derivative soluble in dilute NaOH, compound AAA is Option A.

  5. Comparison with stored answer

    Stored correct answer = A.

    Our derived answer also = A.

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