pKa of Compounds

H2 S O4

H2 S O4

-3

protonated ketone

-7

protonated alcohol on benzene

-6

ROH2+

-2.4

hydronium ion H3O+

-1.7

nitric acid HNO3

-1.3

nitrous acid HNO2

3.3

Benzene +NH3

4.6

Carboxylic Acid R-COOH (H in the OH)

5

the hydrogen between two ketones

9

HCN

9.5

Ammonium ion NH4+ and RNH3+

9.5

NO2 on an alkane, the proton on the primary Carbon

10

OH group on benzene

10

Proton between two esters

13

Proton between a COOH and a ketone

11

Amide

15

Water or alcohol

16

aldehyde (H on non terminal end)

17

ketone

19

COOH (H on non terminal end)

25

alkyne

25

Nitrile

25

NH3 or RNH2

36

hydrogen on benzene or on a terminal double bond

40

R-H

60