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Question
Write resonance structures of aniline. What is the action of benzene diazonium chloride on ethanol?
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Solution
a. Resonance structure of aniline:
In aniline and other arylamines, the amino group is directly attached to benzene ring. Conjugation of lone pair of electrons stabilizes aniline. The lone pair is not easily available for protonation. Five resonance structures of aniline are as follows:
b. Action of benzene diazonium chloride on ethanol:
Reduction of benzene diazonium chloride in the presence of ethanol gives benzene. The ethanol gets oxidized to ethanal.
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