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JEE Main levelSingle correct optionDifficulty 2 of 3g1255

The cation shown is much more stable than the ethyl cation even though oxygen is electronegative. This is because

  1. Aan oxygen lone pair is donated to the empty p orbital (+M effect), giving a structure with complete octets
  2. Boxygen is electropositive and pushes electrons by +I
  3. Cthe cation is stabilised by five hyperconjugating hydrogens
  4. Doxygen is sp hybridised and strongly stabilises the cation

Answer: A

The cation shown is the methoxymethyl cation. The lone pair on oxygen donates into the empty p orbital (+M effect), giving a structure with oxygen-carbon double bond and complete octets. This resonance outweighs the -I effect of oxygen.
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