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JEE Main levelSingle correct optionDifficulty 2 of 3hx098

The experimental dipole moments are about for cyclohexyl chloride and for chlorobenzene. The best explanation of the lower value for chlorobenzene is that

  1. Achlorine is less electronegative when attached to a benzene ring
  2. Bthe ring carbon is more electron-attracting than an carbon and chlorine donates electrons into the ring by resonance, so the C-Cl bond is less polar
  3. Cthe C-Cl bond in chlorobenzene is longer than in cyclohexyl chloride
  4. Dthe pi cloud of the ring carries an equal and opposite dipole that exactly cancels part of the moment

Answer: B

In chlorobenzene Cl is bonded to an carbon, which is more electronegative than carbon, so the charge separation is smaller. In addition, the (lone pair donation) effect of Cl opposes its effect. Both reduce the C-Cl polarity. The bond is in fact shorter, not longer, in chlorobenzene.
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