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Basics of Organic Chemistry question

2007 · Shift 0 · Q3
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Basics of Organic Chemistry question

2007 · Shift 0 · Q3

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Presence of a nitro group in a benzene ring
  1. A
    activates the ring towards electrophilic substitution
  2. B
    renders the ring basic
  3. C
    deactivates the ring towards nucleophilic substitution
  4. D
    deactivates the ring towards electrophilic substitution
View written solutionFree

Correct answer: D

  1. Effect of nitro group on benzene ring

    The nitro group, −NO2-NO_2−NO2​, is a strong electron-withdrawing group.

    It withdraws electron density from the benzene ring by:

    • −I-I−I effect (inductive effect)
    • −M-M−M effect (mesomeric/resonance withdrawing effect)

  2. Effect on electrophilic substitution

    In electrophilic substitution, the benzene ring must act as an electron-rich nucleophile to attack the electrophile.

    Since −NO2-NO_2−NO2​ withdraws electron density from the ring, the ring becomes less reactive toward electrophiles.

    Therefore, the nitro group deactivates the benzene ring toward electrophilic substitution.

  3. Check each option

    • A: activates the ring towards electrophilic substitution
      False. −NO2-NO_2−NO2​ is deactivating, not activating.

    • B: renders the ring basic
      False. Electron withdrawal does not make the ring basic.

    • C: deactivates the ring towards nucleophilic substitution
      False. Electron-withdrawing groups like −NO2-NO_2−NO2​ generally favor nucleophilic aromatic substitution under suitable conditions.

    • D: deactivates the ring towards electrophilic substitution
      True.

  4. Final answer

    The correct option is D.

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