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In $\ce{H^a-CH_2-CO-H^b}$, why is $\ce{H^a}$ more acidic than $\ce{H^b}$ ? From what I know, $\alpha$ hydrogen ($\ce{H^a}$) is highly acidic and is easily abstracted in presence of base $\ce{OH^-}$. But why is $\ce{H^b}$ not abstracted in the similar fashion?

$\ce{C}$ is electronegative because of the $+I$ effect it exerts on $\ce{O}$. Since, $\ce{H^b}$ is more nearer to the $\ce{C}$, shouldn't it be more acidic as the bond pair is more shifted towards the carbonyl carbon?

deechitpoudel
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    The problem is that removal of H in the latter case causes resonance stabilization while in the other one it does not. – Sawarnik Apr 01 '17 at 19:41
  • related http://chemistry.stackexchange.com/questions/12232/acidity-of-aldehydes – Mithoron Apr 01 '17 at 20:15

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