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Question

How do you distinguish between chlorobenzene from benzyl chloride?


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Solution

Chlorobenzene

Chloromethyl benzene

  • The chlorine atom is bonded to the aromatic carbon atom in Chlorobenzene.
  • The chlorine atom is bonded to the aliphatic carbon atom in Chloromethyl benzene.
  • The hybridization of carbon with which chlorine is attached is sp2
  • The hybridization of carbon to which chlorine is attached is sp3
  • Because the connected Chlorine atom is directly bonded to benzene and has a lone pair, it is difficult to break the Carbon-Chlorine bond.
  • Because the linked Chlorine atom is not directly attached to the ring, it is easier to break the Carbon-Chlorine bond.
  • There is no reaction when chlorobenzene is heated with alcoholic silver nitrate (AgNO3)

C6H5Cl(l)Chlorobenzene+AgNO3(l)SilvernitrateNoreaction

  • When Chloromethyl benzene is treated with alcoholic silver nitrateAg(NO3), a white precipitate is produced.

C7H7Cl(l)Chloromethylbenzene+AgNO3(l)SilvernitrateC9H12O(l)Benzylethylether+AgCl(l)Silverchloride(Whiteppt)+HNO3(l)Nitricacid

  • Chlorobenzene (Phenyl chloride)
  • Chloromethyl benzene (α-Chlorotoluene Benzyl chloride)

Therefore, chlorobenzene and chloromethyl benzene can be distinguished on basis of hybridization, and the silver nitrate test.


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