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JEE Main levelSingle correct optionDifficulty 2 of 3hx255

Compared with 1-chloropropane under identical conditions (, dry acetone), the compound shown reacts:

  1. Amuch faster, because the transition state is stabilised by overlap with the adjacent pi bond
  2. Bmuch slower, because the double bond withdraws electrons by resonance from the C-Cl carbon
  3. Cat the same rate, because both are primary halides
  4. Dnot at all, because the carbon bearing chlorine is sp2 hybridised

Answer: A

The compound is allyl chloride. In the SN2 transition state the p orbital on the reacting carbon overlaps with the adjacent pi bond, lowering the transition-state energy, so allylic halides react much faster than comparable saturated primary halides. It is not an sp2-halide (the Cl is on an sp3 carbon), so it is not inert.
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