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Question

When an aromatic amine A was treated with alcoholic potash and another compound Y, a foul-smelling gas was formed with formula C6H5NC. Y was formed by reacting a compound Z with Cl2 in presence of slaked lime. The compound Z is:

A
C6H5NH2
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B
CH3OH
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C
CH3CH2OH
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D
CHCl3
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Solution

The correct option is C CH3CH2OH
In Hoffmann's carbylamine test (also known as Isocyanide test), aliphatic or aromatic primary amine (A) is heated with chloroform (compound Y) in presence of alcoholic potassium hydroxide to give foul smelling alkyl/aryl isocyanide or carbylamine.
Compound Y (chloroform) is obtained by reaction of compound Z (CH3CH2OH) with chlorine in presence of slaked lime.
C6H5NH2A+CHCl3+3KOHheatC6H5NC+3KCl+3H2O
CH3CH2OHZ+3Cl2CCl3CHO+3HCl
2CCl3CHO+Ca(OH)22CHCl3Y+(HCOO)2Ca

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