Sciencemadness Discussion Board

aromatic chlorination CuCl2 ?

Mn2Dc - 28-11-2017 at 15:15


Id like to know how CuCl2 chlorinates xylene toluene and benzene. It seems that the nucleus of benzene is chlorinated
by CuCl2, but wil this also occur on xylenes and toluene ? with
toluene wil i get chlorotoluene or benzylchloride ? if chlorination
of xylenes and toluene wil be as same as for benzene, wil the chlorination happen on the pare or meta position of the aromatic ring.

:P

aga - 28-11-2017 at 16:03

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Sandman3232 - 28-11-2017 at 16:58

Quote: Originally posted by Mn2Dc  

Id like to know how CuCl2 chlorinates xylene toluene and benzene. It seems that the nucleus of benzene is chlorinated
by CuCl2, but wil this also occur on xylenes and toluene ? with
toluene wil i get chlorotoluene or benzylchloride ? if chlorination
of xylenes and toluene wil be as same as for benzene, wil the chlorination happen on the pare or meta position of the aromatic ring.

:P



I think it clorinates the functional groups rather than the bensene ring. Also if you do get cucl to clorinate it would most likely be a ortho/para reaction as CH3 is a weak activating group. Although what exactly do you want to do?

Sandman3232 - 28-11-2017 at 17:07

Quote: Originally posted by Mn2Dc  

Id like to know how CuCl2 chlorinates xylene toluene and benzene. It seems that the nucleus of benzene is chlorinated
by CuCl2, but wil this also occur on xylenes and toluene ? with
toluene wil i get chlorotoluene or benzylchloride ? if chlorination
of xylenes and toluene wil be as same as for benzene, wil the chlorination happen on the pare or meta position of the aromatic ring.

:P


A


I think it clorinates the functional groups rather than the bensene ring. Also if you do get CuCl2 to clorinate xylene/toluene it would most likely be a ortho/para reaction as CH3 is a weak activating group. Also if it reacts with xylene the ortho vs para percentage ratio would most likely depend upon styrical hindrance. Might also help if you say what exactly you want to accomplish ?

Mn2Dc - 1-12-2017 at 15:08

I like to produce a chloro benzene instead of a benzylchloride

Sandman3232 - 2-12-2017 at 13:25

React with a metal halide ( AlCl3, CuCl3 etc.) as catalyst and clorine gas if you want to make clorobenzene. Do some research.