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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Identify the correct decreasing order of the amount of enol form present at equilibrium for the following compounds: (I) ( CH ₃ )₃ CCHO (II) (III)

Options

  1. A(I) > (III) > (II)
  2. B(II) > (III) > (I)
  3. C(I) > (II) > (III)
  4. D(III) > (II) > (I)

Correct answer

D. (III) > (II) > (I)

Step-by-step solution

The stability of the enol form determines the extent of enolization at equilibrium. Compound (I) is ( CH ₃ )₃ CCHO . The -carbon is bonded to three methyl groups and has no -hydrogens. Thus, it cannot form an enol, and its enol content is zero. Compound (II) is cyclohexanone. It has -hydrogens and forms cyclohex-1-en-1-ol as its enol. The keto form is more stable than the simple enol form, so the enol content is very low but non-zero. Compound (III) is cyclohexa-2,4-dien-1-one. It undergoes tautomerization to form

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