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I wonder if ethers are more or less acidic at the alpha position than alkanes ($\mathrm{p}K_\mathrm{a} \approx 50$). I'm not sure if the stabilising inductive effect from oxygen or the alpha effect (the repulsion between lone pairs on the carbanion and the adjacent oxygen) will dominate.

Based on $\ce{H2O}$ ($\mathrm{p}K_\mathrm{a} \approx 16$) vs $\ce{H2O2}$ ($\mathrm{p}K_\mathrm{a} \approx 11.5$), I would expect the inductive effect to be stronger, but I would like to check.

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    $\begingroup$ A good rule of thumb is: everything is more acidic than alkanes. $\endgroup$ – Ivan Neretin Dec 11 '17 at 12:53
  • $\begingroup$ @IvanNeretin Thanks! So you would say that the inductive effect dominates over the alpha effect in this case? Is this a general case? $\endgroup$ – GingerBadger Dec 11 '17 at 18:02
  • $\begingroup$ Yes, I think so. $\endgroup$ – Ivan Neretin Dec 11 '17 at 18:18

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