Chemistry - STRUCTURAL ISOMERISM Question with Solution | TestHub

Explanation

To find out the compound which has highest % enol content in the liquid

Concept This question is based on Keto enolization and percent enol content.

Solution

In Ph–CO–CH(CH₃ )–CHO the proton that is removed to form the enol is α-to two carbonyl groups (a

diketone system: ketone + aldehyde). Enolization at this position gives an enol that is:

• Stabilized by conjugation

The C=C–C=O system formed in the enol is conjugated and resonance-stabilized.

• Hydrogen bonding

The enol –OH can form intramolecular H-bonding with the adjacent C=O, increasing stability. The

compound has strong active methylene group shows chelation in enol form.