VIBRANT ACADEMY ORGANIC CHEMISTRY

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(Micro-XI) Important pKa values
Compound pKa Compound pKa
H2O 15.7
HSbF6 (Super acid) –12 CH3CH2OH 16.0
H3O+ –1.7
CH3SO3H –1.2 16
OH
O2N NO2
O
||
Pricric acid 0.3 CH 3CH 17
NO2 (CH3)3COH 18
CCl3COOH 0.77 Ph – C  CH 19
Oxalic acid 1.2, 4.2 O
Squaric acid 1.5, 3.5
|| 20
CH 3CCH 3
O
|| O
HCOH 3.8 || 24.5
CH 3COEt

4.2 HCCH 25

NH2
O 27
||
CH 3COH 4.8
(C6H5)3CH 31.5
H2CO3 6.4
NH3 36
O O
|| ||
8.9 41
CH 3CCH 2 CCH 3
HCN 9.1 CH2=CH2 44

46
10.0
CH4 50
CH3 – NO2 10.2 _______________________________________________
Amino-acid

10.7 NH3 (9.69)

Alanine (Neutral)
O O COOH (2.34)
|| ||
CH 3CCH 2C–O–C 2H 5 11
NH3 (9.82)
O O Aspartic acid (Acidic) HOOC
|| || (3.86)
C 2H 5 –O–C–CH 2–C–O–C 2H 5 13 COOH (2.09)

NH3 (8.95)
15
NH
Lysine (Basic) H3N COOH
CH3OH 15.5 (10.79) (2.18)
CHCl3 15.5

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 Acidic strength order from NCERT (pKa data based)

CF3COOH > CCl3COOH > CHCl2COOH > NO2CH2COOH > NC-CH2COOH > FCH2COOH > ClCH2COOH >
BrCH2COOH > HCOOH > ClCH2CH2COOH > C6H5COOH > C6H5CH2COOH > CH3COOH > CH3CH2COOH

Direct attachment of groups such as phenyl or viny to the carboxylic acid, increases the acidity of
correspoinding carboxylic acid, contrary to the decrease expected due to resonance effect shown below :

O –
O
H2C = CH — C H2C — CH = C
OH
OH

This is because of greater electronegativity of sp2 hybridised carbon to which carboxyl carbon is attached.
The presence of electron withdrawing group on the phenyl of aromatic carboxylic acid increases their acidity while
electron donating groups decrease their acidity.
_______________________________________________________________________________________________

Compound Resonance Energy (Kcal/mol)

1. Benzene 36

2. Naphthalene 61

3. Anthracene 83

4. Phenanthrene 91

5. Pyridine 28
N

6. Furan 16
O

7. Thiophene 29
S

8. Pyrrole 22
NH

9. Cyclopentadiene 3

10. Butadiene 4
11. Ethene CH2=CH2 0

N
12. Imidazole 22
NH

Vibrant Academy (I) Pvt. Ltd. "B-41(A)" Road No.2, IPIA, Kota (Raj.) Ph. 0744-3507788 (www.vibrantacademy.com) [2]