[Traumatic Acid]

Hi all
Doing some homework on the bromination of aromatics.

Initially I assumed that a bromine would steal a H from the CH3, opening the carbon to an electrophile, thus forming (Benzene)-CH2Br.

Apparently not

I've just found that when toluene is brominated the bromine attaches itself in the orto position. Why is this? I would have thought that if this be the case the CH3 would have  either done nothing, or drawn some electrons away opening that section up to attack from a nucleophile.

Does bromination of toluene specifically form in the ortho position or can it fomr anywhere?

Quick edit, I've added a quick diagram to demostrate.
Another quick edit, this reaction was performed in concentrated acetic acid

Cheers

[chenbeier]

Check the inductive effect. The I-effect of substituents.
The other thing are the parameters. The bss-rule. Boiling heat, sun light side =  chain reaction.
And ccc-rule cold temperature, catalyst = core reaction

[Babcock_Hall]

A reaction at the benzylic position (the methyl group) is possible, but under completely different conditions than reactions that occur on the aromatic ring itself, which I suspect is the intent of the problem.  I suggest that we defer any discussion of other reactions until after we have exhausted the subject of ortho, meta, or para substitutions.