Alkyl benzenes also react at the ortho and para positions

Alkyl benzenes also react at the ortho and para positions 

This is what happens when toluene (methylbenzene) meets bromine  

Electrophilic attack occurs on alkyl benzenes so that the positive charge ends up on the carbon bearing the alkyl group. This carbon is tertiary, making the cation there more stable. This condition is fulfilled if toluene is attacked at the ortho position, as shown above, but also at the para position, because in both cases the positive charge is delocalized onto the same three carbons atoms. 

on the other hand, the electrophile were to attack at the meta position, the charge would end up delocalized over three carbon atoms, none of which are tertiary, so no stabilization by the alkyl group is possible. The situation is no worse than that of benzene, but given that toluene reacts some 10 times faster than benzene at the ortho and para positions these reactions win out. Nonetheless, unlike phenol, toluene does give trace amounts of meta-substituted products. 

475 we described how to observe the cationic intermediate in electrophilic substitution reactions of benzene by protonation in an NMR tube using a supetacid. In benzene the cation which forms is symmetrical. Doing the same experiment with toluene leads to protonation in the para position. 

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ALKYL BENZENES ALSO REACT AT THE ORTHO AND PARA POSITIONS... 

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