# Acidity of ethers vs alkanes

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.

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