Arrange the following aryl halides in decreasing order of reactivity towards Aromatic Nucleophilic Substitution (): p-nitrofluorobenzene (I), p-nitrochlorobenzene (II), p-nitrobromobenzene (III).

Question

Arrange the following aryl halides in decreasing order of reactivity towards Aromatic Nucleophilic Substitution ($S_NAr$): p-nitrofluorobenzene (I), p-nitrochlorobenzene (II), p-nitrobromobenzene (III).

Prashant Kotian · Accepted Answer

Correct answer: C. In the addition-elimination mechanism, the rate-determining step is nucleophilic attack forming a carbanion. Fluorine's intense effect stabilizes this intermediate best, making most reactive.

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