JEE Main · 2025 · Shift-IImediumHALO-025

The structure of the major product formed in the following reaction is:

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

The structure of the major product formed in the following reaction is:

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Options
  1. a

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  2. b

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  3. c

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  4. d

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Correct Answerb

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Detailed Solution

Step 1: Identify the reaction

Aryl/alkyl halide + AgCN → cyanide substitution

AgCN can act as a nucleophile where \ceCN\ce{CN-} replaces the halogen.

Step 2: Determine which halogen is replaced

The substrate has:

  • Br at one position (on benzene ring)
  • Cl at another position (on benzene ring or side chain)

For nucleophilic substitution:

  • Reactivity order: I > Br > Cl > F
  • Better leaving group = faster substitution

But wait, for aryl halides (halogen directly on benzene ring):

  • Nucleophilic aromatic substitution (SNArS_NAr) is very difficult
  • Requires strong electron-withdrawing groups (like \ceNO2\ce{NO2}) to activate the ring
  • Without activation, aryl halides don't undergo simple SN2S_N2 or SN1S_N1

If the structure has:

  • Br on the benzene ring (aryl bromide) - unreactive
  • Cl on a side chain (alkyl chloride) - reactive

Then \ceCN\ce{CN-} will replace the alkyl Cl, not the aryl Br.

Step 3: Determine the product

Major product: CN replaces Cl (more reactive position), Br remains on the ring.

Answer: (b)

Key Points:

  • Aryl halides (X on benzene ring) are unreactive toward simple nucleophilic substitution
  • Alkyl halides (X on side chain) undergo SN2S_N2/SN1S_N1 readily
  • Leaving group ability: I > Br > Cl > F (for alkyl halides)
  • SNArS_NAr requires activation by electron-withdrawing groups

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