Acid Conj.

Base pKa Comment

SO 3 / FSO 3H/SbF 5 SbF6 –
Super Acids
HF / SbF5 SbF6 – –??
F 3CSO3H all too strong to measure
F 3CSO3–
HClO 4 ClO4– –10

Increasing Base
HI I– –10
Increasing Acid

Strength
H 2SO 4 HSO 4– –9 sulfuric acid
Strength

HBr Br – –9 hydrobromic acid

H H
C H
R O+ C
R O –8 protonated aldehydes

OR' OR'
–7 protonated esters
C H C
R R O
O+
HCl Cl – –7 hydrochloric acid
R'
R'
–7 protonated ketones
C H C
R R O
O+
OH OH
H C –6 protonated carboxylic acids
C R O
R O+

H H
+ O –6 protonated phenols
X O X
H
O
OH O
S O
S
O aka TsOH –3 sulfonic acids
H 3C O
H 3C
H
+
O O –3 protonated ethers
R R' R'
R
H
+
O O –2 protonated alcohols
R H R H

H 3O+ H 2O –1.74 hydronium; H +(aq)

HNO 3 NO 3– –1.3 nitric acid

HSO 4– SO 42– 1.99 second H of sulfuric acid

H–F F– 3.18 hydrofluoric acid
HNO 2 NO 2– 3.3 nitrous acid
H
+N H N H
H H
–6 to +5 anilines; pKa very sensitive
to ring substituents
X X
 Acid Conj. Base pKa Comment
O O
4.0 to 5.0 carboxylic acids
C C
R O-H R O

H 2CO3 HCO 3– 6.35 carbonic acid

H 2S HS – 7.00 hydrogen sulfide
Increasing Acid

O O O O
Strength

C C C C 9.00 2,4-pentandione

Increasing Base
H 3C C CH 3 H 3C C CH 3

Strength
H H H
NH 4+ NH 3 9.24 ammonium ion
H
X O X O 4–11 depends on substitution
plain phenol has a pka=10
R–CH 2 –NO2 R–CH–NO 2 10.0 aliphatic nitro
HCO 3– CO3– 10.3 bicarbonate
O O O O
C C C C 11.0 ethyl acetoacetate
H 3C C OEt H 3C C OEt
H H H
O O O O
C C C C
EtO C OEt EtO C OEt 13.0 diethyl malonate
H H
H
H–O–H OH – 15.7 water pKa
H 15.0
H H cyclopentadiene: World's
Strongest Carbon Acid!!
O O
H H
C R
C
N 17.0 amides
R N
H

R–O–H R O 16-19 alcohols, ethanol pKa = 16

O O
H
C C 20-21 alpha H of ketones
R C H R C H
H H
O O
H
C C 25 alpha H of esters
RO C H RO C H
H H

R–CH 2 –CN R–CH–CN 25 alpha to nitrile

R C C H R C C 25 terminal alkynes.
The electrons are in an
sp hybridized orbital
 Acid Conj. Base pKa Comment
H
N 18–28 anilines; pKa Depends on
H N substitution. Low because it
H
X
has a conjugated base.
X Plain aniline has pKa =25

H2 H 36 hydrogen gas is a weak acid

Increasing Acid
Strength

amines: NH 3 pKa=38

Increasing Base
((CH 3)2CH)2NH ((CH 3)2CH)2N – 40

Strength
H H
H
C C benzyl hydrogens;
H 41
H conjugated base

H H allyl hydrogens; conjugated

C
H
C 43
H C C H C C H conjugate base.
H
H H
H H

H H vinyl hydrogens; electrons

44
C C
H C H H C in unconjugated sp2 orbital
H H

H H H H phenyl hydrogens; electrons

44
H C H H C in unconjugated sp2 orbital,
H H H H not part of aromatic π sextet

H 2C
H H 2C
C H
C 46 cyclopropane H; more vinyl
H 2C H than sp3 hybrid (see below.)
H 2C

H H

H
C H C 48 methane and hydrogens on
H
H
H sp3 carbons

H H
H H H H H H
H H H H
H H 52 cyclohexyl; weakest acid on
H
this table. sp3 conj. base
H H H H H H H H

updated 9/6/2016