Given below are two statements:
Statement (I) : All the following compounds react with p-toluenesulfonyl chloride.
$C_6H_5NH_2 \quad (C_6H_5)_2NH \quad (C_6H_5)_3N$
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) : All the following compounds react with p-toluenesulfonyl chloride.
$C_6H_5NH_2 \quad (C_6H_5)_2NH \quad (C_6H_5)_3N$
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.
- Both Statement I and Statement II is false
- 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
The Correct Option is A
Approach Solution - 1
To solve the given problem, we need to analyze the two statements provided with respect to the chemical reactivity of the compounds with p-toluenesulfonyl chloride and the solubility of the resultant products in aqueous NaOH.
Analysis of Statement I:
Statement I claims that: "All the following compounds react with p-toluenesulfonyl chloride."
The compounds listed are: \(C_6H_5NH_2\) (aniline), \((C_6H_5)_2NH\) (diphenylamine), and \((C_6H_5)_3N\) (triphenylamine).
Explanation:
- Aniline (\(C_6H_5NH_2\)): A primary amine, reacts with p-toluenesulfonyl chloride to form a tosylamide.
- Diphenylamine (\((C_6H_5)_2NH\)): A secondary amine, can react to form a tosyl derivative but typically less reactive than primary amines.
- Triphenylamine (\((C_6H_5)_3N\)): A tertiary amine, which generally does not react with p-toluenesulfonyl chloride under normal conditions.
Therefore, Statement I is false because triphenylamine does not react with p-toluenesulfonyl chloride.
Analysis of Statement II:
Statement II claims that: "Their products in the above reaction are soluble in aqueous NaOH."
Explanation:
- The products of aniline and diphenylamine reacting with p-toluenesulfonyl chloride are tosylamides.
- Tosylamides are generally not soluble in aqueous NaOH as they do not possess acidic hydrogens that can result in salt formation.
Thus, Statement II is false because the products are not soluble in aqueous NaOH.
Conclusion:
The correct answer is: "Both Statement I and Statement II is false".
Approach Solution -2
The reaction with p-toluenesulfonyl chloride (TsCl) is known as the Hinsberg test, which is specific for 1$^\circ$ amines.
Only 1$^\circ$ amines (C$_6$H$_5$NH$_2$) react with TsCl to form sulfonamides that are soluble in aqueous NaOH.
2$^\circ$ amines ((C$_6$H$_5$)$_2$NH) react with TsCl to form sulfonamides that are insoluble in NaOH.
3$^\circ$ amines ((C$_6$H$_5$)$_3$N) do not react with TsCl at all.
Thus:
Statement I: False. Not all the given compounds react with TsCl.
Statement II: False. Only the sulfonamide formed by 1$^\circ$ amines is soluble in NaOH.
Top Questions on Amines
- Give the structures of A, B, and C in the following reaction sequences: (i)\; \(\mathrm{CH_3CH_2I} \xrightarrow[\ ]{\mathrm{NaCN}} A \xrightarrow[\ ]{\;\;HO^-\;/\;H_2O\;\;} B \xrightarrow[\;Br_2/NaOH\;]{} C\)
(ii)\; \(\mathrm{C_6H_5N_2^+Cl^-} \xrightarrow[\ ]{\mathrm{CuCN}} A \xrightarrow[\ ]{\;H_3O^+\;} B \xrightarrow[\ \Delta\ ]{\;NH_3\;} C\)
(iii)\; \(\mathrm{CH_3CH_2Br} \xrightarrow[\ ]{\mathrm{KCN}} A \xrightarrow[\ ]{\mathrm{LiAlH_4}} B \xrightarrow[\;273\,K\;]{\;HNO_2\;} C\) - How can you obtain the following?
(a) Aniline from ammonium benzoate
(b) Benzene diazonium chloride from nitrobenzene
(c) 2,4,6-Tribromoaniline from aniline - Arrange the following compounds in increasing order of their boiling point:
\[ \text{(CH}_3\text{)}_2\text{NH, CH}_3\text{CH}_2\text{NH}_2, \text{CH}_3\text{CH}_2\text{OH} \] Amines are usually formed from amides, imides, halides, nitro compounds, etc. They exhibit hydrogen bonding which influences their physical properties. In alkyl amines, a combination of electron releasing, steric and H-bonding factors influence the stability of the substituted ammonium cations in protic polar solvents and thus affect the basic nature of amines. Alkyl amines are found to be stronger bases than ammonia. Amines being basic in nature, react with acids to form salts. Aryldiazonium salts, undergo replacement of the diazonium group with a variety of nucleophiles to produce aryl halides, cyanides, phenols and arenes.
How can you convert the following:
(i) Ethanoic acid to methanamineWhich of the following amine(s) show(s) positive carbamylamine test?
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