How to distinguish between chlorobenzene and chlorocyclohexane by a chemical reaction?
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Chlorobenzene and Chlorocyclohexane gives different product on reaction with silver nitrate solution, it is used to distinguish the two compounds.
It is because in chlorocyclohexane , the C-Cl bond is of sp3 hybridization, which follows nucleophilic reaction, but in chlorobenzene , the C-Cl bond is related with an sp2hybridized carbon atom and the C-Cl bond has a partial double bond character due to resonance, so it does not undergo nucleophilic reaction.
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