ACID BASE BALANCE

ACID-BASE EQUILIBRIAM

• CARBOXYLIC ACIDS LIKE ACETIC ACID IS A WEAK ACID,

AND THE POSITION OF ITS EQUILIBRIUM LIES VERY FAR TO
THE LEFT

-
CH3 COOH + H2 O CH3 COO + H3 O+
Acetic acid Acetate ion
ACID IONIZATION CONSTANTS

WHEN A WEAK ACID, HA, DISSOLVES IN WATER, THE EQUILIBRIUM

CONSTANT, KEQ, FOR THIS IONIZATION IS
- +
HA + H2 O A + H3 O

BECAUSE WATER IS THE SOLVENT AND ITS CONCENTRATION CHANGES

VERY LITTLE WHEN WE ADD HA TO IT, WE TREAT [H2O] AS A CONSTANT

[A-] [H3 O+ ]
Keq =
[HA][ H2 O]

[ A- ][ H3 O+ ]
Ka = Ke q[H2 O] =
[HA]
 ACID IONIZATION CONSTANTS
BECAUSE THE ACID IONIZATION CONSTANTS FOR WEAK ACIDS
ARE NUMBERS WITH NEGATIVE EXPONENTS, WE COMMONLY
EXPRESS ACID STRENGTHS AS PKA WHERE

pKa = -log Ka
The weaker the acid, the smaller its Ka, but the larger its pKa
•Values of Ka for most unsubstituted aliphatic and aromatic
carboxylic acids fall within the range 10-4 to 10-5 (pKa 4.0 - 5.0)
O O
- +
CH3 COH + H2 O CH3 CO + H3 O

[ CH3 COO- ] [ H3 O+ ]
Ka = = 1.74 x 10-5
[ CH3 COOH]
pK a = 4.76
Acid Name Ka pKa
H3 PO4 Phosphoric acid 7.5 x 10-3 2.12
HCOOH Formic acid 1.8 x 10-4 3.75
-4
CH3 CH( OH)COOH Lactic acid 8.4 x 10 3.08
-5
CH3 COOH Acetic acid 1.8 x 10 4.75
H2 CO3 Carbonic acid 4.3 x 10-7 6.37
Dihydrogen phosphate ion 6.2 x 10-8
-
H2 PO4 7.21
-1 0
H3 BO3 Boric acid 7.3 x 10 9.14
+ -1 0
NH4 Ammonium ion 5.6 x 10 9.25
HCN Hydrocyanic acid 4.9 x 10-1 0 9.31
C6 H5 OH Phenol 1.3 x 10-1 0 9.89
- -1 1
HCO3 Bicarbonate ion 5.6 x 10 10.25
2- -1 3
HPO4 Hydrogen phosphate ion 2.2 x 10 12.66
 ACIDITY OF RCOOH
• SUBSTITUENTS OF HIGH ELECTRONEGATIVITY, ESPECIALLY -
OH, -CL, AND -NH3+, NEAR THE CARBOXYL GROUP INCREASE
THE ACIDITY OF CARBOXYLIC ACIDS
• BOTH DICHLOROACETIC ACID AND TRICHLOROACETIC ACID
ARE STRONGER ACIDS THAN H3PO4 (PKA 2.1)

Formula: CH3 COOH ClCH2 COOH Cl2 CHCOOH Cl3 CCOOH

Name: Acetic Chloroacetic Dichloroacetic Trichloroacetic
acid acid acid acid
pK a: 4.76 2.86 1.48 0.70
Increasing acid strength