JEE Main 2025 Jan 28 Shift 1, Chemistry Q14: Properties of Alkyl Halides (Halo Alkanes) & Aryl Halides (Halo Arenes)

JEE Main2025Jan 28, Shift 1Chemistry

The products A and B in the following reactions, respectively are

$A Ag-NO_{2} CH_{3} -CH_{2} -CH_{2} -Br AgCN B$

A
CH $_{3}$ -CH $_{2}$ -CH $_{2}$ -ONO, CH $_{3}$ -CH $_{2}$ -CH $_{2}$ -NC
B
CH $_{3}$ -CH $_{2}$ -CH $_{2}$ -ONO, CH $_{3}$ -CH $_{2}$ -CH $_{2}$ -CN
C
CH $_{3}$ -CH $_{2}$ -CH $_{2}$ -NO $_{2}$ , CH $_{3}$ -CH $_{2}$ -CH $_{2}$ -CN
D
CH $_{3}$ -CH $_{2}$ -CH $_{2}$ -NO $_{2}$ , CH $_{3}$ -CH $_{2}$ -CH $_{2}$ -NC

Solution

Both AgNO $_{2}$ and AgCN are ambident nucleophiles. Because of the largely covalent silver-N bond, the carbon-substrate sees the nitrogen end of each reagent more readily, so the attacking atom is N in both cases.

With AgNO $_{2}$ , the alkyl halide picks up the NO $_{2}$ group through nitrogen, giving the nitroalkane CH $_{3}$ CH $_{2}$ CH $_{2}$ -NO $_{2}$ (product A).

With AgCN, attack through nitrogen gives the isocyanide CH $_{3}$ CH $_{2}$ CH $_{2}$ -NC (product B).

$∴$ A = 1-nitropropane, B = propyl isocyanide. Option (4).

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JEE Main 2025 Jan 28 Shift 1, Chemistry Q14: Properties of Alkyl Halides (Halo Alkanes) & Aryl Halides (Halo Arenes)

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