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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g1272

Select all correct statements about the compound shown.

  1. AThe nitro group is twisted out of the plane of the benzene ring
  2. BThe -R (resonance) effect of the nitro group is largely inhibited
  3. CThe -I effect of the nitro group is completely lost
  4. DThe ortho and para carbons are as electron-poor as in nitrobenzene

Answer: A, B

The compound shown is 2,6-dimethylnitrobenzene. Steric repulsion by the two ortho methyl groups twists the nitro group out of the ring plane (A true), which inhibits the -R effect (B true). The -I effect is a through-bond effect that remains (C false). Since resonance withdrawal is reduced, the ortho and para carbons are less electron-poor than in nitrobenzene (D false).
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