Which of the following compounds will show the maximum enol content?
A
CH3COCH3
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B
CH3COCH2COCH3
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C
CH3COCH2COOC2H5
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D
CH3COCH2CONH2
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Solution
The correct option is BCH3COCH2COCH3 (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.