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NEET levelSingle correct optionDifficulty 1 of 3hx263

Compound shown does not react with aqueous at room temperature, unlike a typical alkyl chloride. The main reason is:

  1. AThe C-Cl bond is stronger (sp2 carbon, partial double-bond character from resonance) and backside attack is blocked by the ring
  2. BChloride is a very poor leaving group from every type of carbon
  3. CThe benzene ring contains no pi electrons that can interact with chlorine
  4. DThe compound is too non-polar to be attacked by any nucleophile

Answer: A

The compound is chlorobenzene. Its chlorine is on an sp2 carbon and its lone pair is delocalised into the ring, giving the C-Cl bond partial double-bond character and extra strength; in addition, backside attack is blocked by the ring and the phenyl cation is unstable. Hence neither SN1 nor SN2 occurs readily.
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