[University_Of_Toronto]

Rank the following compounds in order of increasing acidity.

ethanol
 fluoromethanol
 tert-butanol
 

[ARGOS++]

Dear University_Of_Toronto,

Please:   What would be YOUR first approach and WHY?

Good Luck!
                    ARGOS⁺⁺

[Mahmoud]

ethanol
fluoromethanol
tert-butanol

The order is fluoromethanol then tert-butanol then ethanol
because F electron with drawing group which decrease charge density over C atom and make H easy to go
but methyl group is electron donating group which increase charge density over C atom and make H harder to go

Thanks

[University_Of_Toronto]

Thanks buddy!!!

[kanan]

the answer is very easy and controlled by the inductive effect
so fluoro..> ethanol >tert-butanol >
the ease of proton in tert-butanol is ls=ess than in ethanol due to having 4 methyl group compared with ethanol as one group only, which mean less stable conjugated base than in ethanol.

[macman104]

I agree with kanan.  Mahmoud, it should be ethanol then t-butanol.