The structure of the major product formed in the following reaction is:
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
The structure of the major product formed in the following reaction is:
- a
- b✓
- c
- d
Step 1: Identify the reaction
Aryl/alkyl halide + AgCN → cyanide substitution
AgCN can act as a nucleophile where 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 () is very difficult
- Requires strong electron-withdrawing groups (like ) to activate the ring
- Without activation, aryl halides don't undergo simple or
If the structure has:
- Br on the benzene ring (aryl bromide) - unreactive
- Cl on a side chain (alkyl chloride) - reactive
Then 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 / readily
- Leaving group ability: I > Br > Cl > F (for alkyl halides)
- requires activation by electron-withdrawing groups
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