We know C-C bond is much stronger than C-OH bond (because similar sized atoms have maximum overlap)as in case of phenyl-cabonyl carbon bond. Also due to resonance there is double bond character in phenyl-carbon linkage.Then how does that bond break to give phenyl shift?

  • $\begingroup$ The rearrangement is driven by the (effectively irreversible) deprotonation of the carboxylic acid, not by bond strengths $\endgroup$ – orthocresol Jun 17 '16 at 17:03
  • $\begingroup$ I have a feeling you didn't read en.wikipedia.org/wiki/Benzilic_acid_rearrangement which describes mechanism well. $\endgroup$ – Mithoron Jun 17 '16 at 23:04
  • $\begingroup$ I have a feeling you didn't read my question well as I asked why phenyl shifts instead of oxygen linkages as oxygen have lone pairs to form three member cyclic transition state easily than phenyl whose bond strength is much high even to form that trasition ring easily than -OH @ Mithoron $\endgroup$ – Swastik Jun 18 '16 at 13:24

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