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Question: Answered & Verified by Expert
Keto-enol tautomerism is not shown by
ChemistryGeneral Organic ChemistryJEE Main
Options:
  • A butan-2-one
  • B 1-phenylbutan-2-one
  • C p-O2NC6H4CH2COCH2Ph
  • D PhCOPh
Solution:
1134 Upvotes Verified Answer
The correct answer is: PhCOPh
The compounds A, B and C show keto-enol tautomerism.

A. CH3-C||O-CH2CH3CH3-C=|      OH   CH-CH3i             H2C=C-|     OH   CH2CH3ii     

The first enol is more stable, because it has the more substituted double bond.

B. PhCH2-C||O-CH2-CH3PhCH=C-|      OH   CH2-CH3i          PhCH2-C=|     OH   CH-CH3ii   

The first enol is more stable, because C=C and Ph are conjugated.

C. p-O2NC6H4CH2COCH3p-O2NC6H4CH=C|-OH     CH3                                        (i)p-O2NC6H4CH2C|=OH    CHPh                              (ii)

The first enol is more stable, because the p-O2N extends the delocalization of the conjugated system.

PhCOPh does not show tautomerism as do not have any α -H-atom.

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