The compound that undergoes decarboxylation most readily under mild condition is
(A)(see structure)
(B)(see structure)✓ Correct
(C)(see structure)
(D)(see structure)
Answer: (B)
Solution
β-keto acids undergo decarboxylation most readily under mild conditions through a cyclic six-membered transition state. Option (B) shows a β-keto acid (2-oxocyclohexanecarboxylic acid) where the carboxyl group is at the β-position to the ketone, making it the most susceptible to decarboxylation. The answer is (B).
JEE Advanced · 2012 · 08 Apr 2012 · Paper 2 · Single correct option
