Selected pKa Values

Acid pKa Conjugate Base

Strongest acid Sulfuric acid H2SO4 -9 HSO4- Weakest base

Hydroiodic acid HI -9 I-

Hydrobromic acid HBr -8 Br-

Protonated ketone -7.3

" "

Hydrochloric acid HCl -7.0 Cl-

Protonated ether R2OH+ -3.6 ROR

Protonated alcohol ROH2+ -2 ROH

Hydronium ion H3O+ (*) -1.7 H2O

Carboxylic acid 5
" "

Dihydrogen phosphate H2PO4- 7.2 HPO42-

1,3-Diketone α H 9
" " (enolate ion)

Ammonium ion NH4+ 9.4 NH3

Phenol 9.9
" "

Thiol RSH 10.5 RS-

RNH3+, R2NH2+, RNH2, R2NH,

Protonated amines 11
R3NH+, R3N,

1,3-Diester α H 13.3
" " (enolate ion)

Amide 15-16
"

Water H2O (*) 15.7 HO-

Primary alcohol RCH2OH 16 RCH2O- (alkoxide ion)

Tertiary alcohol R3COH 18 R3CO- (alkoxide ion)

Aldehyde α H 17
" "

Kline - SMC - Last revised 8/1/2017

 Selected pKa Values
Acid pKa Conjugate Base

Ketone α H 20
" " (enolate ion)

Ester α H 25
" " (enolate ion)

Allkyne " 25 " (alkynide ion)

Hydrogen H2 35 H- (hydride ion)

Ammonia NH3 38 NH2- (amide ion)

Amine RNH2, R2NH RNH-, R2N- (amide ion)

Alkene 44
" "

Weakest acid Alkane 50 Strongest base

" "

R = a hydrocarbon alkyl group such as methyl or ethyl.

(*) There is some controversy about the pKa values for H+ and water.. General chemistry books typically use the
thermodynamic values of 0.00 and 14.00, respectively. Organic chemistry books typically use what are referred to as the
“rational” values that are cited here.

Kline - SMC - Last revised 8/1/2017