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Question
Carboxylic acids contain carbonyl group but do not show the nucleophilic addition reaction like aldehydes or ketones. Why?
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Solution
It is due to resonance as shown below. The partial positive charge on the carbonyl carbon atom is reduced
Similarly, a carbonyl group of aldehydes and ketones may be regarded as the resonance hybrid of the following structures.
The carbonyl carbon of carboxylic group is less electrophilic than carbonyl carbon in aldehydes and ketones and hence nucleophilic addition reactions of aldehydes and ketones do not takes place with carboxylic acids.
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