Weird Rxn, What's Going On Here?

[NumbaOneStunna]

This was in Achiever I think, a methylbenzene with Cl2 and hv makes a benzene with a Cl directly attached to it with a CH3 attached to the Cl. Wth is going on?

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[kkmaths90]

I am little confused here...you mean to say the answer is

Benzene ring - Cl-CH3 ?? hmm never seen that before. I thought it was Benzene ring -CH2Cl Someone explain please

 

[suhshi]

This was in Achiever I think, a methylbenzene with Cl2 and hv makes a benzene with a Cl directly attached to it with a CH3 attached to the Cl. Wth is going on?

Benzlic halogenation proceeds through radical intermediates
The halogen will not attack the carbon in the benzene ring bc that would destroy the aromatic character of the benzene ring

 

[SupahShyGuy]

Hey numba!

If you were expecting the Cl to attach to the benzene ring (btw. methylbenzene is also known as toluene) you would need to utilize Cl2 with a Lewis Acid such as FeCl3 or AlCl3 in which the intermediates would make (AlCl4- and Cl-), that then will safely attach to the methylbenzene (or toluene) without destroying aromaticity at the para-position or ortho-position if there may be a substituent on para.

Good luck guys!