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Which of the following will be the least reactive towards nucleophilic substitution reaction?

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Aryl halides are least reactive towards nucleophilic substitution because the \(C-X\) bond has partial double bond character due to resonance.
Updated On: Jun 29, 2026
  • Fig A
  • Fig B
  • Fig C
  • Fig D
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The Correct Option is B

Solution and Explanation

Step 1: Understand what affects nucleophilic substitution reactivity.
Nucleophilic substitution (SN) reactions require the carbon bearing the halogen to be electron-poor enough for the nucleophile to attack. The ease of C-X bond breaking determines reactivity.
Step 2: Recall the effect of the benzene ring on the C-X bond.
In aryl halides, the halogen is directly attached to the sp2-hybridised carbon of the benzene ring. The lone pairs of the halogen participate in resonance with the pi-system of the ring, giving the C-X bond partial double-bond character.
Step 3: Resonance in aryl halides makes the carbon electron-rich.
Due to resonance donation of the halogen lone pair into the ring, the carbon bearing the halogen becomes electron-rich (not electron-poor). This strongly opposes nucleophilic attack, which requires an electron-deficient carbon.
Step 4: Why aryl halides are least reactive in SN reactions.
Both electronic and steric factors work against SN in aryl halides: (i) the carbon bearing the halogen is electron-rich due to resonance, (ii) the C-X bond has partial double-bond character making it harder to break, (iii) the flat aromatic ring blocks backside attack needed for SN2.
Step 5: Compare reactivity order of different halide types.
Reactivity in SN: allylic and benzylic > alkyl > vinyl and aryl. Vinyl and aryl halides are least reactive because of resonance stabilisation of the C-X bond. Alkyl halides react readily by SN1 or SN2.
Step 6: Identify Fig B as the least reactive.
Fig B shows an aryl halide (halogen directly on the benzene ring). It is least reactive towards nucleophilic substitution due to resonance strengthening of the C-X bond and the electron-rich nature of the ipso carbon. \[ \boxed{\text{Fig B (aryl halide) is least reactive towards nucleophilic substitution}} \]
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