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I understand that deprotonation from the carbon circled in red is feasible because deprotonation results in a resonance-stabilised structure. But according to it, deprotonation is also feasible in blue-circled carbon. Then why is that the red carbon hydrogens are more acidic?

  • 2
    $\begingroup$ Aldol reactions like this are thermodynamically controlled, so which hydrogen is most acidic isn't the issue here, it's which product is the most stable. $\endgroup$
    – orthocresol
    Oct 26, 2021 at 15:09
  • 1
    $\begingroup$ I can see here not two but five acidic centers. All of them would be deprotonated to some extent, but what comes later is important, as ortho said. $\endgroup$
    – Mithoron
    Oct 26, 2021 at 18:52


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