The compound that undergoes decarboxylation most readily under mild condition is :
-Keto acids undergoes decarboxylation most readly.
Decarboxylation is a chemical reaction where a carboxylic acid loses a carbon dioxide molecule to form a hydrocarbon or a substituted hydrocarbon. The ease of decarboxylation depends on the stability of the intermediate formed and the nature of the carboxylic acid.
Beta-keto acids and malonic acids undergo decarboxylation readily under mild conditions because they form a stable six-membered cyclic transition state or a resonance-stabilized enol intermediate. The decarboxylation mechanism involves:
Step 1: Intramolecular hydrogen bonding or proton transfer facilitates the reaction.
Step 2: Formation of a cyclic transition state (for beta-keto acids) or enol intermediate.
Step 3: Release of CO and formation of the final product.
Among the given options, the compound that is a beta-keto acid will decarboxylate most readily. Without the exact structures, based on typical examples:
- Option 1: Likely a simple carboxylic acid (less readily decarboxylates).
- Option 2: Could be a malonic acid derivative (decarboxylates readily).
- Option 3: Might be a beta-keto acid (decarboxylates most readily).
- Option 4: Possibly an alpha-keto acid (requires harsh conditions).
The beta-keto acid (option 3, if it is one) undergoes decarboxylation most readily due to the stabilization of the enol intermediate and low energy transition state.
Decarboxylation Reaction: General reaction for beta-keto acid:
Stability Factors: Resonance stabilization and cyclic transition state lower the activation energy.
Key Compounds: Acetoacetic acid (beta-keto acid) and malonic acid decarboxylate easily.