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JEE Main levelOne or more correct optionsDifficulty 2 of 3g1087

In which of the following compounds is resonance of a substituent with the ring significantly diminished by steric inhibition of resonance?

  1. AN,N,2,6-tetramethylaniline
  2. B2,6-dimethylbenzoic acid
  3. C3,5-dimethyl-4-nitrophenol
  4. D4-nitrophenol

Answer: A, B, C

In the first three compounds, two groups flank the conjugating substituent and force it out of the ring plane: , and respectively, so their orbital overlap with the ring is lost. In 4-nitrophenol the nitro group is unhindered and coplanar.
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