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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

  1. AY is a solid which dissolves in aqueous NaOH.
  2. BY is a solid which dissolves in aqueous HCl.
  3. CX does not react with Hinsberg's reagent, hence Y is not formed.
  4. 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

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