$\mathrm{CH}_{3} \mathrm{NH}_{2}+\mathrm{CHCl}_{3}+\mathrm{KOH} \rightarrow$ Nitrogen containing compound $+\mathrm{KCl}+\mathrm{H}_{2} \mathrm{O}$. Nitrogen containing compound is

(D) $\mathrm{CH}_{3} \stackrel{+}{\mathrm{N}} \equiv \overline{\mathrm{C}}$

(A) $\mathrm{CH}_{3}-\mathrm{C} \equiv \mathrm{N}$

(B) $\mathrm{CH}_{3}-\mathrm{NH}-\mathrm{CH}_{3}$

(C) $\mathrm{CH}_{3}-\stackrel{-}{\mathrm{N}} \equiv \stackrel{+}{\mathrm{C}}$

JEE Advanced · 2006 · 09 Apr 2006 · Compounds Containing Nitrogen

CH_{3} NH_{2} + CHCl_{3} + KOH \to

Nitrogen containing compound

+ KCl + H_{2} O

. Nitrogen containing compound is

(A) $CH_{3} - C \equiv N$
(B) $CH_{3} - NH - CH_{3}$
(C) $CH_{3} - N - \equiv C +$
(D) $CH_{3} N + \equiv \overline{C}$ ✓ Correct

Answer: (D)

Solution

This is the carbylamine reaction (isocyanide test). Primary amines react with chloroform and alcoholic KOH to form isocyanides (carbylamines). The product is methyl isocyanide:

CH_{3} NH_{2} + CHCl_{3} + 3 KOH \to CH_{3} N \equiv C + 3 KCl + 3 H_{2} O

. The correct representation is

CH_{3} N + \equiv \overline{C}

, showing the zwitterionic character.

JEE Advanced · 2006 · 09 Apr 2006 · Single correct option

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JEE Advanced · 2006 · 09 Apr 2006 · Compounds Containing Nitrogen

Solution

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