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JEE Main · 2026 · 21 Jan 2026 · Shift 2 · Haloalkanes and Haloarenes

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The correct order of reactivity of the following benzyl halides towards reaction with KCN is:
  1. (A)
  2. (B)
    ✓ Correct
  3. (C)
  4. (D)

Answer: (B)

Solution

Reaction of these benzyl bromides with cyanide proceeds through a benzylic carbocation, so the rate is set by how well each ring stabilises that positive charge. A para-amino group is the strongest electron donor and lends the most stabilisation; a para-hydroxy group donates strongly but somewhat less; a meta-nitro group withdraws only inductively and destabilises mildly; and a para-nitro group withdraws by both induction and direct resonance and destabilises most. With the structures labelled a (p-OH), b (p-amino), c (p-nitro) and d (m-nitro), the reactivity order is .

JEE Main · 2026 · 21 Jan 2026 · Shift 2 · Single correct option

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