Given below are two statements, one is labelled as Statement I and the other is labelled as Statement II. Statement (I) : All the following compounds react with p-toluenesulphonyl chloride. [ C 6 H 5 NH 2 ; ( C 6 H 5 ) 2 NH ; ( C 6 H 5 ) 3 N ] Statement (II) : Their products in the above reaction are soluble in aqueous NaOH . In the light of the above statements, choose the correct answer from the options given below.

Statement I is true but Statement II is false

Statement I is false but Statement II is true

Both Statement I and Statement II is true

Chemistry · Nitrogen Containing Organic Compounds

JEE Main 2024 — 8 April, Shift 2 — Question 71

Given below are two statements, one is labelled as Statement I and the other is labelled as Statement II.

Statement (I) : All the following compounds react with p-toluenesulphonyl chloride.

[ $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2} ;\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \mathrm{NH} ;\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{~N}$ ]

Statement (II) : Their products in the above reaction are soluble in aqueous NaOH .

In the light of the above statements, choose the correct answer from the options given below.

Option A:
Both Statement I and Statement II is false
Correct
Option B:
Statement I is true but Statement II is false
Option C:
Statement I is false but Statement II is true
Option D:
Both Statement I and Statement II is true

Answer: A

Step-by-step solution

Statement I is False: p-Toluenesulphonyl chloride $(TsCl)$ reacts only with amines having at least one $N-H$ bond. $\mathrm{C_6H_5NH_2}$ (primary amine) and $(\mathrm{C_6H_5})_2\mathrm{NH}$ (secondary amine) react with $TsCl$ , whereas $(\mathrm{C_6H_5})_3\mathrm{N}$ (tertiary amine) does not react because it has no $N-H$ bond. Hence, it is incorrect to say that all the given compounds react with $TsCl$ .

Statement II is False: The products formed are not all soluble in aqueous NaOH. The sulphonamide formed from a primary amine contains an acidic $N-H$ group and is soluble in $NaOH$ , whereas the sulphonamide formed from a secondary amine does not contain an acidic $N-H$ group and is insoluble in $NaOH$ .

Thus, Both Statement I and Statement II is false.

Answer key and solution verified before publishing.

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Exam: JEE Main 2024
Paper: 8 April, Shift 2
Subject: Chemistry
Chapter: Nitrogen Containing Organic Compounds
Topic: Chemical properties of Amines