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JEE Main levelSingle correct optionDifficulty 2 of 3g3240

The singlet carbene shown is much more stable than singlet methylene. What is the main reason?

  1. AThe carbene carbon carries a full positive charge.
  2. BHyperconjugation with the C-H bonds of the methyl group fills the p orbital.
  3. CThe carbene carbon is sp hybridised with two unpaired electrons.
  4. DA lone pair on oxygen is donated into the empty p orbital on the carbene carbon.

Answer: D

The carbene shown is chloro(methoxy)carbene. In a singlet carbene the carbon has a filled sp orbital and an empty p orbital. The lone pair on the alpha oxygen (and to a smaller extent on Cl) overlaps with this empty p orbital, which lowers its energy and stabilises the singlet state. The carbon is not charged, not sp, and the methyl group is attached to oxygen, too far for useful hyperconjugation.
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