Amines Ques 22

22. Which one of the following on reduction with lithium aluminium hydride yields a secondary amine?

[2007]

(a) Methyl isocyanide

(b) Acetamide

(c) Methyl cyanide

(d) Nitroethane.

Show Answer

Solution:

  1. (a) Reduction of alkyl isocyanides in presence of $LiAlH_4$ yields secondary amines containing methyl as one of the alkyl group.

$ \begin{aligned} & R-N \triangleq C+4[H] \xrightarrow{LiAlH_4} R-NH-CH_3 \\ & 2^{\circ} \text{ amine } \\ & \text{ e.g., } CH_3-N \nRightarrow C+4[H] \xrightarrow{LiAlH_4} \\ & CH_3-NH-CH_3 \\ & \text{ dimethyl amine } \end{aligned} $

whereas, alkyl cyanides give $1^{\circ}$ amine on reduction.



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