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Question

The organic compound that undergoes carbylamine reaction is:

A
(C2H5)2NH
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B
C2H5NH2
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C
(C2H5)3N
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D
(C2H5)4N+I
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Solution

The correct option is B C2H5NH2

Carbylamine reaction mechanism includes the addition of amine to the intermediate created from the dehydrohalogenation of chloroform. This intermediate is called dichlorocarbene. The carbylamine reaction is also known as Hoffmann isocyanide synthesis. It is the reaction of a primary amine, chloroform and a base to synthesize isocyanides. The dichlorocarbene intermediate is very important for this conversion. The carbylamine reaction cannot be used to synthesize isocyanides from secondary or tertiary amines.

Carbylamine reaction is given by only primary amine. Hence C2H5NH2 gives carbylamine reaction as it is the only primary amine out of the given options.
RNH2+CHCl3+3KOH(alcoholic)ΔRNC+3KCl+3H2O
Hence, (b) is the correct option.

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