I am familiar with electrophilic substitutions of benzene, with chlorine using a halogen carrier catalyst such as $\ce{AlCl3}$, to produce chlorobenzene, and I am aware of the mechanism. But, apparently, one can get the addition of chlorine to benzene, where the delocalised structure is disrupted and hexachlorocyclohexane is formed.

I would like to know the mechanism for this addition reaction.

  • 1
    $\begingroup$ This is a radical addition, more here chemguide.co.uk/organicprops/arenes/halogenation.html $\endgroup$ – Waylander Apr 24 '19 at 15:11
  • $\begingroup$ Thank you for referring me to the chemguide link but this only discusses the overall equation of the addition reaction, it does discuss the mechanism of the monosubstitution of chlorine into the benzene ring but I am trying to find information out about the complete chlorination of the benzene ring, i.e., the addition of 3 chlorine molecules to get C6H6Cl6, Thanks $\endgroup$ – Davidmb65 Apr 24 '19 at 22:08
  • $\begingroup$ @Waylander's link is useful if realize that the reaction is a radical chain reaction and not electrophilic aromatic substitution. $\endgroup$ – user55119 Jun 17 '19 at 16:44

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