Transcript
Chemistry 130A M. E. Jung Spring 2001 Organic Acids and Bases Acid
pKa
Acid
pKa
Base
pKa (of conj. acid)
CH2 (NO2) 2
4
(CH3)3 COH
19
BuLi
45
CH3 CO2H
5
PhCOCH 3
19
RMgBr
45
Ph3PCH 2CO2Et
6
CH3 COCH3
20
PhLi
40
(CH3)2 CHNO2
8
NaH/KH
~37
NCCH2CO2Et
9
R2NLi
36
CH3 CH2NO2
9
+
CH2
20
Ph2NH
21
NH2 -
35
(CH3)3 CCOCH3
21
CH3 SOCH2-Na+
35
Ph3C -
31
tBuO-
19
CH3 NO2
10
PhOH
10
Me3NH +
10
CH2
CH3 COCH2CO2 Et
11
CH3 SO2CH3
23-7
EtO-
18
CH3 CH(COCH3)2
11
CH3 CO2Et
25
MeO -
17
CH2 (CN)2
11
CH3 CN
25
HO-
16
CH3 SH
12
H-C
25
Na2CO3
12
CH2 (CO2Et)2
13
CH2
15
23
C-H
PhNH 2
27
Ph3CH
31
Ph2CH2
33
N
(CH2)n
11-13
N n = 1,3 DBN, DBU
H2O
16
CH3 SOCH 3
35
N
PhCH 2COPh
16
NH3
35
PhO-
10
(CH3CH2 )2NH
36
R3N
10
[(CH 3)2CH]2NH
36
ImH
7
PhCH 3
37
NaHCO3
7
CH2 =CH-CH3
38
PhNEt2
6
PhH
40
pyridine
5
R-H
45-52
AcO-
5
O2N
NHPh 16
CH3 OH
17
CH3 COCH2Cl
17
CH3 CH2OH
18
(CH3)2 CHOH
18
+
CH3 PPh3
18
NMe2
10-12
