Appendix

4. pKa Table and how to use it

The pKa values can be used to estimate the equilibrium constant of any acid base
reaction. Consider the following reaction:

K eq
A H B A H B

where A-H is any Brønsted acid and :B is any Brønsted base. If we know pKa(A-H)
and pKa(H-B+), Keq can be calculated through the following equation (For derivation
see Chemistry3, 2:ed, page 315):

pKeq = pKa(A-H) - pKa(H-B+)

pKeq = -logKeq

Since Keq is the ratio between the concentration of the right hand side products and
the left hand substrates:

Keq = [A-] [H-B+] / [A-H] [:B]

we land at the following conclusions:

Keq > 1 or pKeq < 1 reaction pushed to the right side

Keq < 1 or pKeq > 1 reaction pushed to the left side

Example:
O K eq O

F 3C OH F 3C O OH2
OH

pK a = 0 pK a ≈ -2
-2
pKeq =0 - (-2) = 2 → Keq = 10

The equilibrium for this acid base reaction lies to left side where one out of 100
molecules of cyclohexanol will be protonated.

K eq H
N Li N
H Li

pK a ≈ 25 (LDA) pK a = 37

pKeq =25-37 = -12 → Keq = 1012

For deprotonation of acetylenes using LDA (lithium diisopropylamide), the

equilibrium is completely pushed to the product side. This is a convenient way to
generate a strong carbon nucleophile that can be used for formation of the important
carbon-carbon bond.

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pKa Table of some compounds commonly encountered in organic chemistry.
Table 2
SOME APPROXIMATE pKa VALUES
O O
H3C NH -10 11
OR
HBr -5 H
(CN)3CH -5 H2O2 12
Strong Mineral Acids <0
O O
13
OH RO OR
-7 H
F3C O 12
H
CH3OH2 -2
O 14
Cl H
H3O -1.6 O
H O 15
NH2
0
NH2 H2O 15-16
CF3CO2H 0 R OH 16-18
R CO2H 4-6
OH 18
HN3 5
O
5 H
H 17
N
H O
H
19-20
NH3
O
5 H 24-25
OR
H
H2S 7 CN 25
H2NNH3 8 R

R C C H 25
R CO3H 8
O
HCN 9 H ~30
NR2
R2NH2 10
FENOL 10 (C6H5)3PCH3 35
R CH2NO2 10
NH3 33
RSH 11
(i-Pr)2NH 37

O O CH3
41
9
H
R CH3 ≈50
RSH 11

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