why Neculeophile reaction is less Favourable in Phenol
Naqash Rasheed , 10 Years ago
Grade 12
Organic Chemistry> why Neculeophile reaction is less Favoura...
1 Answers
sufi digital
Last Activity: 10 Years ago
nucleophilic reaction is less favourable in phenols because of
- resonance- C-OH bond acquires partial double bond character due to resonance and hence bond clevage is difficult
- instability of intermediate phenyl cation formed in case of Sn1 mechanism
- phenol is electron rich as OH group is electron donating hence it repulses nucleophiles which are also electron rich
- 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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