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  4. Arrange the following in the increasing order of expected enol content CH3COCH2 CHO, CH3 COCH3 , CH3CHO, CH3COCH2 COCH3

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Q. Arrange the following in the increasing order of expected enol content
$ CH_3COCH_2 CHO, CH_3 COCH_3 , CH_3CHO, CH_3COCH_2 COCH_3 $

IIT JEEIIT JEE 1992Aldehydes Ketones and Carboxylic Acids

Solution:

$CH _{3}- CO - CH _{2}- COCH _{3}$ has highest enol content due to resonance and formation of six membered ring through intramolecular H-bonding
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Also, enol content depends upon the number of substituents on double bond, greater the number of substituents, greater the stability, higher the enol content.
Therefore, $CH _{3} COCH _{2} CHO$ forms next most stable enol