NEETChemistryAmines
Methyl isocyanide on reduction with LiAlH ₄ yields compound X. When compound X is treated with Hinsberg's reagent, it forms a product Y. Which of the following statements is correct regarding the nature of product Y?
Options
- AY is a solid which dissolves in aqueous NaOH.
- BY is a solid which dissolves in aqueous HCl.
- CX does not react with Hinsberg's reagent, hence Y is not formed.
- DY is a solid which remains insoluble in aqueous NaOH.
Correct answer
D. Y is a solid which remains insoluble in aqueous NaOH.
Step-by-step solution
Reduction of methyl isocyanide ( CH ₃ NC ) with LiAlH ₄ yields dimethylamine ( CH ₃ NHCH ₃ ), which is a secondary ( 2^ ) amine. This is compound X. When a secondary amine reacts with Hinsberg's reagent (benzenesulphonyl chloride), it forms an N,N-dialkylbenzenesulphonamide (product Y). In this case, N,N-dimethylbenzenesulphonamide is formed. Because there is no hydrogen atom attached to the nitrogen atom in this product, it is not acidic and therefore remains insoluble in aqueous alkali (NaOH). Note: Reduction of