Which of the following compounds will show the maximum enol content?

C H_{3} C O C H_{3}

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C H_{3} C O C H_{2} C O C H_{3}

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C H_{3} C O C H_{2} C O O C_{2} H_{5}

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C H_{3} C O C H_{2} C O N H_{2}

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Solution

The correct option is B $C H_{3} C O C H_{2} C O C H_{3}$
(a)

As can be seen from the structure, there no additional stability with the 'enol' form.
(b)

This enol form is highly stable because of intramolecular $H -$ bonding ( $6$ membered stability) and due to extended conjugation.
(c)

(d)

In both the compounds (c) and (d), $C - 2$ of $C = O$ group is a part of the acid derivative (ester and acid amide). So, $C - 2, C = O$ will not take part in enolisation, because it is already in resonance $- R$ with the derivative group itself.

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