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
- A(I) > (III) > (II)
- B(II) > (III) > (I)
- C(I) > (II) > (III)
- 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