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Question

Why does the NO2 group show its effect only in ortho?


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Solution

Ortho positions :

In organic chemistry, an ortho position is one in which two identical functional groups are bound to positions 1 and 2 of a benzene ring.

Resonating structures in nitrobenzene:

  1. The presence of NO2 groups at the ortho and para positions pushes electron density away from the benzene ring, facilitating the nucleophile's interaction very easily.
  2. Also, the negative charge is not stabilized by the presence of the nitro group at the meta position.
  3. The existence of the NO2 group at the meta position has no impact on reactivity.

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