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Question

Which of the following cannot undergo nucleophilic substitution under ordinary conditions?

A
Chlorobenzene
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B
Tert-butyl chloride
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C
Iso-propyl chloride
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D
None of the above
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Solution

The correct option is C Chlorobenzene
Chlorobenzene undergoes nucleophilic substitution under a drastic condition because due to resonance C-Cl bond acquire some double-bond character as a result substitution of -Cl by nucleophile becomes difficult ordinary condition.

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