Why is 1-fluoroethanol more acidic than ethanol?

[bomba923]

Is 1-fluoroethanol significantly more acidic than regular ethanol?

(Not just "slightly" more acidic)

What about 1-chloroethanol? Is it significantly more acidic than regular ethanol?

(see the attached image for structures of these molecules)

 

[movies]

1-chloroethanol isn't stable. It will decompose into acetaldehyde and HCl. You might be able to produce fleeting amounts of it in the gas phase, but it probably wouldn't stick around long enough to measure the pKa.

For what it's worth, 2-flouroethanol is only moderately more acidic than ethanol (pKas of 14.42 and 15.18, respectively).

 

[bomba923]

Hm, I see / /

~Thanks for the quick response!