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Compounds Containing Nitrogen question

2022 · 26 Jun · Shift 2 · Q13
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  5. /2022 · 26 Jun · Shift 2 · Q13

Compounds Containing Nitrogen question

2022 · 26 Jun · Shift 2 · Q13

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Which statement is NOT correct for p-toluenesulphonyl chloride?
  1. A
    It is known as Hinsberg's reagent.
  2. B
    It is used to distinguish primary and secondary amines.
  3. C
    On treatment with secondary amine, it leads to a product, that is soluble in alkali.
  4. D
    It doesn't react with tertiary amines.
View written solutionFree

Correct answer: C

  1. Identify the reagent

ppp-Toluenesulphonyl chloride is commonly called Hinsberg's reagent.

So, Option A is correct.


  1. Its use in distinguishing amines

Hinsberg's reagent is used in the Hinsberg test to distinguish among primary, secondary, and tertiary amines.

In particular, it helps distinguish primary and secondary amines based on the solubility of the sulphonamide formed.

So, Option B is correct.


  1. Reaction with primary and secondary amines

(i) Primary amine

A primary amine reacts with ppp-toluenesulphonyl chloride to form an NNN-substituted sulphonamide:

RNH2+TsCl→TsNHR+HClRNH_2 + TsCl \rightarrow TsNHR + HClRNH2​+TsCl→TsNHR+HCl

This product still contains one acidic hydrogen on nitrogen, so it dissolves in alkali by forming its sodium salt.

(ii) Secondary amine

A secondary amine reacts as:

R2NH+TsCl→TsNR2+HClR_2NH + TsCl \rightarrow TsNR_2 + HClR2​NH+TsCl→TsNR2​+HCl

The product has no hydrogen on nitrogen, so it is not acidic and therefore insoluble in alkali.

Thus, the statement:

"On treatment with secondary amine, it leads to a product, that is soluble in alkali"

is incorrect.

So, Option C is NOT correct.


  1. Reaction with tertiary amines

Tertiary amines, R3NR_3NR3​N, do not have an N−HN-HN−H bond and hence do not form sulphonamides with Hinsberg's reagent under test conditions.

So, Option D is correct.


  1. Final conclusion

The statement which is NOT correct is:

C\boxed{\text{C}}C​
  1. Comparison with stored correct answer

Stored correct answer: CCC

My derived answer: CCC

They match.

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