pKa values - orgo

HI

Halogen Acid

I-

-10, pretty strong acid

HBr

Halogen Acid

Br-

-9, strong

HCl

Halogen Acid

Cl-

-8, strong

HF

Halogen Acid

F-

+3, strong, most electronegative but small so not as strong as HI

H3O+

Other strong acid

H2O

-2, strong

H2S

weak acids

HS-

+7

NH4+

weak acids

NH3

+9

NH3

weak acids

NH2-

+35

H2O

weak acids

-OH

+16

ROH2+

organic oxyacid: alcohol

ROH

-2

ROH

organic oxyacid: alcohol

RO-

+16

carboxylic acid, O=OH

organic acid: other oxyacids

O=O-

+5

if CH3, +4.7

Benzene+OH

organic acid: other oxyacids

benzene+O-

+10

CH3- benzene- S with double bonded O and OH

organic acid: other oxyacid

same but OH missing an H+

-3

methyl+H

organic acid carbon acids

(CH3-)

+50

H2C=CH2

organic acid carbon acid

H2C=CH-

+44

HC Triple bond CH

organic acid carbon acid

HC trip bond C -

+25

N trip bond C—H

organic acid carbon acid

N trip bond C -

+9.2

org acid carbon acid

+20