pKa Chart 2

1
conjugate acid conjugate base conjugate acid conjugate base
strongest acids

weakest bases
sulfuric acid H2SO4 HSO4 -10 nitric acid HNO3 -1.3
NO3

hydroiodic acid HI -9
I tosic acid TsOH TsO- -0.6

hydrobromic acid HBr Br -8 hydrofluoric acid 3.2

HF F

H
O O
protonated
-7.3
ketone hydrogen nitride HN3 N3 4.7

hydrochloric acid HCl Cl -7

O O
carboxylic acids H 4.8
O O
protonated O O -3.6
ether
H
H
protonated
pyridine 5.2
carbocations -3 NH N

carbonic acid H2CO3 HCO3 6.37

protonated H H
alcohol O O
-2.4 (bicarbonate)
H

hydrogen sulfide H2S SH 7

O
hydronium ion H H O -1.7
H H H
 3 4
conjugate acid conjugate base conjugate acid conjugate base

O O O O water O
O H 15.7
H H
1,3-diketones 9 (hydroxide)

primary alcohols H 16
hydrogen cyanide H C N C N 9.1 O O
(cyanide) (alkoxides)
H
ammonium ions N 9.4 tertiary alcohols
H N H H H O O 18
H
H H (tert-butoxide)
O O
OH O
phenols 10 ketones 18-21
(enolates)
O O
bicarbonate HCO3 - -2
CO3 10.25 esters 25
O O
(ester enolates)
H 10.5 26
thiols S S alkynes C C H C C
(acetylide anions)

H H
protonated H
amines N H3C N 10.6 hydrogen H H H (hydride) 35
H3C H H one way only
H
H N
cyclopentadiene 15 ammonia/amines N 36
weakest acids

H R H R H

strongest bases
H
(aromatic) (amide bases)

O O
amides 15 alkanes ~60
NH2 NH H one way only MgBr
(Grignards/ organolithium reagents)