pKa Values for a Few Common Organic Acids

Stoltz: Chem. 41a

Remember that acidity increases as you go down the list!
alkanes ............................................................................................45-60
n-BuH ................................................................................................50
ethers (PhOCH2H)...........................................................................49
allylic and benzylic (CH)..............................................................40-45
alkenes and arenes (C=CH) ..........................................................36-45
HN(i-Pr)2 .........................................................................................36
NH3 ....................................................................................................35
CH3SOCH2H (DMSO) ...................................................................31
Ph3CH..............................................................................................31
HN(TMS)2 .......................................................................................30
sulfones (PhSO2CH2H) ...................................................................29
acetylenes (CCH) ..........................................................................25
esters and nitriles ............................................................................24-25
ketones and aldehydes ....................................................................20-24
t-BuOH ............................................................................................19
EtOH................................................................................................18
HOH ................................................................................................16
cyclopentadiene .................................................................................15
malonates (HCH(CO2R)2)...............................................................13
-keto esters (CH3COCH2CO2R) .....................................................11
(HNR3)+ ........................................................................................9-11
nitrocompounds .................................................................................10
HCO3Na ..........................................................................................10
HCO3H ........................................................................................... 6.4
pyridinium (Hpyr)+ ......................................................................... 5.2
HO(CO)CH3 (acetic acid) ................................................................. 4.8
HF ................................................................................................... 3.2
p-TsOH ............................................................................................. 1
H3O+ ................................................................................................. 1.7
H2SO4 ................................................................................................ 3
HCl ................................................................................................... 6
HBr ................................................................................................... 9
HI ..................................................................................................... 10
HClO4 .............................................................................................. 10
TfOH................................................................................................ 15
For more comprehensive lists see:
http://www2.lsdiv.harvard.edu/labs/evans/
http://www.chem.wisc.edu/areas/reich/pkatable/index.htm