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why Neculeophile reaction is less Favourable in Phenol

why Neculeophile reaction is less Favourable in Phenol

Grade:12

1 Answers

sufi digital
32 Points
8 years ago
nucleophilic reaction is less favourable in phenols because of
  1. resonance- C-OH bond acquires partial double bond character due to resonance and hence bond clevage is difficult
  2. instability of intermediate phenyl cation formed in case of Sn1 mechanism
  3. phenol is electron rich as OH group is electron donating hence it repulses nucleophiles which are also electron rich
  4. hybridisation- the C-OH bond in phenol is sp2 hybridised and hence has more s- character which makes it more electronegative. so the C-OH bond is more strong which decreases its bond length so it is difficult to break.

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