pKa values

HClO4

ClO4 

–10

HI
(hello)

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–10

RCH(=O+H)
(protonated aldehyde)

RCH(=O)
(aldehyde) 

–10

H2SO4
(sulfuric acid)

HSO4

–10

 

 

HBr

Br

–9

 

HCl

Cl

–7 

R2C(=O+H)
(protonated ketone)

R2C(=O)

(ketone) 

–7

 

 

ArSO3H

ArSO3

–6.5

RC(=O+H)OR’
(protonated ester)

 

RC(=O)OR’
(ester)

–6

 

 

R—O+HR’
(protonated ether)

R—O—R’

(ether) 

–3.5

 

ROH2+
 
(protonated alcohol)

 

ROH

(alcohol)

 

–2

 

 

H3O+



H2O 

–1.7

HNO3

 

 

NO3 

–1.4

 

HSO4

SO42– 

2

 

 

HF

 

F 

3.1

 

 

ArNH3+
(protonated aniline)

ArNH2
(aniline)

4

RC(=O)OH
(carboxylic acid)

RC(=O)O

5

H2CO3


HCO3 

6.4

H2S

HS

7
ArSH
(thiophenol)

ArS

7

MeC(=O)CH2C(=O)Me
(acetylacetone) / (hacac) 

MeCOCHCOMe
(acac)

9 
HCN

CN

9.2

 

 

NH4+

NH3 

9.2

 


 

ArOH
(phenol)

ArO

10

 

 

R—CH2—NO2

R—CH—NO2

10

 

RNH3+

RNH3

11
RSH

RS

11
MeC(=O)CH2C(=O)OMe
(methyl acetoacetate)

MeC(=O)CHC(=O)OMe

11
CH3OH

CH3O

15.2
H2O

HO

15.7
RCH2—OH
(primary alcohol)

RCH2—O

16
R2CH—OH
(secondary alcohol)

R2CH—O

17
R3C—OH
(tertiary alcohol)

R3C—O 

17

MeC(=O)NH2
(acetamide)

 

MeC(=O)NH 

17
MeC(=O)CH3
(ketone)

MeC(=O)CH2

20

MeOC(=O)CH3
(ester)

 

MeOC(=O)CH2 

24
R—CH2—CN

R—CH—CN

25

RCCH
(terminal alkyne)

 

RCC 

25
H2

H

35
NH3

NH2

38

Ph—CH3
(toluene)

 

Ph—CH2 

40
C6H6
(benzene)

C6H5

43
CH2=CH2

CH2=CH

44
CH4

CH3

48
x

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