pKa Chart

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pKa Chart

1

sulfuric acid

H2SO4

H

conjugate acid -10

HSO4

HI

I

-9

HBr

Br

-8

hydroiodic acid

hydrobromic acid

conjugate base

protonated ketone

O

hydrochloric acid

HCl

O

-7.3

weakest bases

strongest acids

conjugate acid

nitric acid

HNO3

tosic acid

TsOH

O

-0.6

3.2

hydrogen nitride

HN3

N3

4.7

O

O O

H

O

4.8

H H

carbocations

protonated alcohol

TsO-

F

-3.6

O

-1.3

NO3

HF

carboxylic acids protonated ether

conjugate base

hydrofluoric acid

-7

Cl

2

-3

H

O

O

H

-2.4

protonated pyridine

carbonic acid

N

NH

H2CO3

HCO3

5.2

6.37

(bicarbonate)

H

hydronium ion

H

O H

hydrogen sulfide H

H

O

H

-1.7

H2S

SH

7

3

conjugate acid O

4

conjugate base O

O

water

O

1,3-diketones

hydrogen cyanide

H

O

conjugate base O

H

9

H

C

H

N

C

N

primary alcohols

9.1

N

H

N

H

O

15.7

H

O

16

(alkoxides)

9.4

H

tertiary alcohols

O

O

H

H

H

(hydroxide)

(cyanide)

H

ammonium ions

conjugate acid

H

(tert-butoxide) O

O

O

OH

ketones

10

phenols

18

18-21 (enolates) O

bicarbonate

-

-2

HCO3

10.25

CO3

esters

O

25

O

O (ester enolates)

thiols

S

H

10.5

S

alkynes

C

C

H

C

C

26

(acetylide anions)

protonated amines

H H3C

N

H

H H3C

H

10.6

N

hydrogen

H

H one way only

H

H

(hydride)

35

H H

15

(aromatic) O

O

amides NH2

15 NH

ammonia/amines

R

N

H

N R H (amide bases)

alkanes

36

~60 H

one way only

MgBr

(Grignards/ organolithium reagents)

strongest bases

H

weakest acids

H

cyclopentadiene

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pKa Chart

pKa Chart 1 sulfuric acid H2SO4 H conjugate acid -10 HSO4 HI I -9 HBr Br -8 hydroiodic acid hydrobromic acid conjugate base protonated...

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