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3 answers

this is standard aromatic chemistry.

the nitro group on nitrobenezene is strongly electron-withdrawing and if you were to draw out the resonance structures of the intermediate cation in this reaction you would see that it is only stabilised when the cation is in the meta position. In general electron-withdrawing groups are meta-directing. In the ortho position you need two atoms adjacent to each other to maintain a positive charge, which is very unstable and would not be preferred over the meta position.

Toluene (or methyl benzene) has a methyl group which is weakly electron donating, by mesomeric effects. This ability helps stabilise the intermediate cations in the ortho and para positions. In general electron-donating groups are ortho / para directing. Depending upon the size / strength of these groups you may be able to direct one over the other.

A mixture of electron-dontaing and electron-withdrawing groups on an aromatic ring helps further direct the substitution of an aromatic species.

The same arguements also hold for some heteroaromatic systems also.

2006-08-13 01:08:11 · answer #1 · answered by Anonymous · 2 0

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2016-12-14 05:01:12 · answer #2 · answered by ? 3 · 0 0

Don't add concentrated sulphuric and nitric acid to toluene. The reaction produces trinitrotoluene - better known as TNT. You'll kill us all!

2006-08-14 16:58:44 · answer #3 · answered by gaitercrew 3 · 0 0

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