Which of the following has higher enol content?


> 
> Which of the following has higher enol content?
> 
> 
> 


[![enter image description here](https://i.stack.imgur.com/PyPtT.png)](https://i.stack.imgur.com/PyPtT.png)


The enol form of (A) and (B) is:


[![enter image description here](https://i.stack.imgur.com/iLxTc.png)](https://i.stack.imgur.com/iLxTc.png)


Both the enols have hydrogen bonding.


If the oxygen were to accept the pi electrns from carbon forming a carbocation like this (a resonance structure):


[![enter image description here](https://i.stack.imgur.com/Y7UWi.png)](https://i.stack.imgur.com/Y7UWi.png)


the compound becomes stabilized due to resonance as well. So isn't (B) the answer?




The two main factors affecting the stability of the enol forms of (A) and (B) are 


1. Hydrogen bonding
2. Aromaticity


In the enol form of both compounds, hydrogen bonding is present:


[![enter image description here](https://i.stack.imgur.com/UZawB.png)](https://i.stack.imgur.com/UZawB.png)


But the resonance structure of enol form of (B) is aromatic. It contains $6$ $\pi$-electrons:


[![enter image description here](https://i.stack.imgur.com/aordV.png)](https://i.stack.imgur.com/aordV.png)


The enol form of (A) lacks this stability. Hence, the enol content of (B) is more than that of (A)


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