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Question
Arrange the following compounds increasing order of acidic strength :
Arrange the following compounds increasing order of acidic strength :
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Solution
The correct option is A III<II<I
Alkyl groups are weakly electron donating, they tend to destabilise anions. This is because they will be "pushing" electrons towards a negative system which is unfavourable electrostatically. In the carbanions derived from trifluoromethyl diketones charge is largely localized on the more electronegative atoms.
In the ester, there is also a resonance donation from the alkoxy group towards the carbonyl that competes with the stabilisation of the enolate charge. This makes the ester enolate less stable so esters are even less acidic.
Therefore the acidic strength order is III<II<I
Alkyl groups are weakly electron donating, they tend to destabilise anions. This is because they will be "pushing" electrons towards a negative system which is unfavourable electrostatically.
In the carbanions derived from trifluoromethyl diketones charge is largely localized on the more electronegative atoms.
In the ester, there is also a resonance donation from the alkoxy group towards the carbonyl that competes with the stabilisation of the enolate charge. This makes the ester enolate less stable so esters are even less acidic.
Therefore the acidic strength order is
III<II<I
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