The bromide shown is converted to compound X as follows: (i) AgNO2, (ii) Sn/HCl, (iii) CHCl3 with alcoholic KOH, heat. Which single reagent, used directly on the bromide shown, gives the same compound X?

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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx258

The bromide shown is converted to compound X as follows: (i) $AgNO X_{2}$ , (ii) $Sn / HCl$ , (iii) $CHCl X_{3}$ with alcoholic $KOH$ , heat. Which single reagent, used directly on the bromide shown, gives the same compound X?

A $KCN$
B $AgCN$
C $KNO X_{2}$
D $AgNO X_{2}$

Answer: B

Step (i) gives nitroethane (N-attack), step (ii) reduces it to ethylamine, and step (iii) is the carbylamine reaction, converting a primary amine to ethyl isocyanide,

CH X_{3} CH X_{2} - N \equiv C

. Direct reaction of ethyl bromide with covalent AgCN also gives ethyl isocyanide; KCN gives the nitrile, and KNO2/AgNO2 give a nitrite or nitro compound.

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The bromide shown is converted to compound X as follows: (i) AgNOX2​, (ii) Sn/HCl, (iii) CHClX3​ with alcoholic KOH, heat. Which single reagent, used directly on the bromide shown, gives the same compound X?

Answer: B

More questions on KCN vs AgCN, KNO2 vs AgNO2, Finkelstein and Swarts on drawn halides

The bromide shown is converted to compound X as follows: (i) $AgNO X_{2}$ , (ii) $Sn / HCl$ , (iii) $CHCl X_{3}$ with alcoholic $KOH$ , heat. Which single reagent, used directly on the bromide shown, gives the same compound X?