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According to me the answer should be (C) as that Carbocation will be stablized by resonance with Chlorine. I have read that resonance is the biggest deciding factor about the stability of a carbocation But some argue that (A) would be most stable as it is farthest away from a highly electronegative Chlorine atom. Please help

  • $\begingroup$ Are you sure B can be discharged out discussion? $\endgroup$ – Alchimista Jan 16 '19 at 13:26
  • $\begingroup$ i do not agree with you because Cl is considered a deactivating(electron withdrawing) groupand the carbon will be very posistive which this itself causes instablitiy. $\endgroup$ – parsa ahmadi Jan 16 '19 at 15:31
  • $\begingroup$ If you're not "supposed to" think about chloronium in such case then such question is pretty much waste of time. $\endgroup$ – Mithoron Jan 16 '19 at 18:08

You are correct as resonance is most powerful factor for stabilisation of carbonation So C is most stable and after that due to hyperconjugation B would be more stable than A. Order for governing stability is


  • $\begingroup$ What about overlap strength? I mean, I know that for fluorine, overlap of lone pairs from 2p of fluorine to empty p of carbocation is quite stabilising. Can the same be said for overlap of empty p of C and 3p of Cl? $\endgroup$ – Yusuf Hasan Jan 16 '19 at 15:14

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