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Question
Which of the following compound has the greater enol content?
Which of the following compound has the greater enol content?
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Solution
The correct option is C
In Keto esters, the ester group is stabilised by internal resonance. So, the −COO group does not stabilise the conjugate base (removal of apha hydrogen) effectively as it happens in ketones.
The enol form of (c) is more stable due to the resonance stability of conjugated double bond and also due to the formation of cyclic six membered ring by hydrogen bonding.
Other enol forms of (a), (b) and (d) lack this stabilisation due to cross conjugation of ester group which will hinder the enolisation.
In Keto esters, the ester group is stabilised by internal resonance. So, the −COO group does not stabilise the conjugate base (removal of apha hydrogen) effectively as it happens in ketones.
The enol form of (c) is more stable due to the resonance stability of conjugated double bond and also due to the formation of cyclic six membered ring by hydrogen bonding.
Other enol forms of (a), (b) and (d) lack this stabilisation due to cross conjugation of ester group which will hinder the enolisation.
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