Which of the following reactions will not give a primary amine?

Which of the following reactions will not give a primary amine?
  1. $\mathrm{CH}_{3} \mathrm{CONH}_{2} \stackrel{\mathrm{Br}_{2} / \mathrm{KOH}}{\longrightarrow}$
  2. $\mathrm{CH}_{3} \mathrm{CN} \stackrel{\mathrm{LiAlH}_{4}}{\longrightarrow}$
  3. $\mathrm{CH}_{3} \mathrm{NC} \stackrel{\mathrm{LiAlH}_{4}}{\longrightarrow}$
  4. $\mathrm{CH}_{3} \mathrm{CONH}_{2} \stackrel{\mathrm{LiAlH}_{4}}{\longrightarrow}$

Solution

$\mathrm{CH}_{3} \mathrm{NC}$ (methyl isocyanide) on reduction with $\mathrm{LiAlH}_{4}$ gives secondary amine. *

Asked in: JEE-TOPICTESTS-CHEMISTRY

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