how to find out which compound which will show maximum enol content in any list of compounds?

Dear Student,

Such determinations are not possible with certainty however, you may predict on the basis of the stability of the keto or enol form and so that you could be able to find the  percentage like if enol form is more stable the content percentage must be more than 50 %.
For this, you need to look the structure of both the forms and find some key features like:
1. If R-groups are equivalent, they cause symmetry and so enol form is more stable,.
2. If inter molecular H- bonding occurs, then molecule will get resonance stabilized and enol form will be stable.
3.If phenyl substituents are present. They also help in resonance and so enol form is more stable and hence the percentage content will be larger.

Regards,

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The extent of enol content can be explained on the basis of acidic hydrogen, intramolecular hydrogen bonding.
 
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