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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Consider the following diazonium ions: I. II. III. IV. The correct increasing order of their reactivity towards azo-coupling reactions (under similar conditions) is:

Options

  1. AIII < I < IV < II
  2. BIII < I < II < IV
  3. CI < III < IV < II
  4. DI < IV < II < III

Correct answer

C. I < III < IV < II

Step-by-step solution

In an azo-coupling reaction, the diazonium ion acts as an electrophile. The reactivity of the diazonium ion towards coupling depends on its electrophilic character. Electron-withdrawing groups (EWGs) on the benzene ring increase the positive charge on the diazonium nitrogen, making it a stronger electrophile and thus more reactive. Conversely, electron-donating groups (EDGs) disperse the positive charge through resonance (+R effect), stabilizing the diazonium ion and making it less reactive. Let us analyze the subs

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