CHEM 333 Acidity and Basicity (pKa) Table

H on SP3 carbon

> 50

H on SP2 carbon

44

amines

35

H on SP carbon

25

alcohols

16-18 (oxygen is more EN than carbon so hydrogens on oxygen are more acidic)

Phenols

9-10 (resonance)

protonated amines

9

thiols

7

carboxylic acids

4-5 (because of the adjacent EWG [C=O] and resonance stabilization)

carboxylic acids with adjacent electronegative groups

0

protonated alcohols

-1.7

H-X

-7

sulfonic acids

-9

Hydrogens on carbons adjacent to C=O

20-25 (C=O are EWGs and the anion that forms is stabilized by resonance)

Hydrogens on carbons adjacent to two C=Os

9-10

the most important parameter in determining the acidity of a proton

the electronegativity of the atom directly connected to the proton

ester

25

aldehyde/ketone

20

Name this compound.

acetone

Name this compound.

acetate