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Show by an arrow the preferred product of reaction with E^(+) of each of the three isomeric, (a) nitrotoluenes, (b) methoxy toluenes and ( c) methoxy acetanilides. Explain your choices in each case. |
Answer» Solution : In (A), `CH_(3)` DIRECTS `E^(+)` to ORTHO and para-positions which are also meta to `NO_(2)`, i.e., substituents reinforce each other. In (B), the orientation is in opposition. The o-p-director controls the orientation, i.e., `E^(+)` enters para to `CH_(3)` and ortho to `NO_(2)`. In (C), both groups are reinforcing, i.e., ortho to `CH_(3)` and meta to `NO_(2)`. Both groups are o- p-directing. In (B), the substituents reinforce each other, very little substitution occurs between the groups due to steric HINDRANCE. In (A)and(C), the two groups ar in opposition. The more strongly activating `-OCH_(3)` controls the orientation. Both the substituents are o- p-directing and equally MODERATE STRONG activators. In (B), both the groups are reingorcing and a mixture of two isomers is obtained. In (A) and (C), two groups are in opposition. In (A), Substantial amounts of all isomers are obtained while in (C), substitution occurs ortho to both the groups. |
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