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pKa Chart

sulfuric acid

H2SO4

conjugate acid
-10

HSO4

HI

-9

HBr

Br

-8

hydroiodic acid

hydrobromic acid

conjugate base

protonated
ketone

hydrochloric acid

HCl

-7.3

weakest bases

strongest acids

conjugate acid

nitric acid

HNO3

tosic acid

TsOH

-0.6

3.2

hydrogen nitride

HN3

N3

4.7

O
O

4.8

H
H

carbocations

protonated
alcohol

TsO-

-3.6

-1.3

NO3

HF

carboxylic acids
protonated
ether

conjugate base

hydrofluoric acid

-7

Cl

-3

-2.4

protonated
pyridine

carbonic acid

NH

H2CO3

HCO3

5.2

6.37

(bicarbonate)

hydronium ion

O
H

hydrogen sulfide
H

-1.7

H2S

SH

conjugate acid
O

conjugate base
O

water

1,3-diketones

hydrogen cyanide

conjugate base
O

primary alcohols

9.1

15.7

16

(alkoxides)

9.4

tertiary alcohols

(hydroxide)

(cyanide)

ammonium ions

conjugate acid

(tert-butoxide)
O

OH

ketones

10

phenols

18

18-21
(enolates)
O

bicarbonate

-2

HCO3

10.25

CO3

esters

25

O
(ester enolates)

thiols

10.5

alkynes

26

(acetylide anions)

protonated
amines

H
H3C

H
H3C

10.6

hydrogen

H
one way only

(hydride)

35

H
H

15

(aromatic)
O

amides
NH2

15
NH

ammonia/amines

N
R
H
(amide bases)

alkanes

36

~60
H

one way only

MgBr

(Grignards/ organolithium reagents)

strongest bases

weakest acids

cyclopentadiene