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Question
Which β- keto acid shown below will not undergo decarboxylation on heating with an acid?
Which β- keto acid shown below will not undergo decarboxylation on heating with an acid?
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Solution
The correct option is B
Generally, β−keto acids undergo decarboxylation under mild condition to give ketone.
When the carboxylic group is present at bridge head carbon, decarboxylation does not take place rather it can undego retro Diels-Alder reaction. the reason behind it, is the formation of unstable enol in the intermediate steps where carbon at bridge head is sp2 hybridised. That induces high tortional strain in the ring and restrict the pathway.
Generally, β−keto acids undergo decarboxylation under mild condition to give ketone.
When the carboxylic group is present at bridge head carbon, decarboxylation does not take place rather it can undego retro Diels-Alder reaction. the reason behind it, is the formation of unstable enol in the intermediate steps where carbon at bridge head is sp2 hybridised. That induces high tortional strain in the ring and restrict the pathway.
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