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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
MgBr
strongest bases
weakest acids
cyclopentadiene