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Brønsted-Lowry Acids and Bases
Brønsted-Lowry Acids and Bases
NH3
CCl 4
CH3
+
H3C
CH3
+
H3C
CH3
CH3
CH2
CA
CB
HO
+
H3C
CH2
CH3
+
H3C
HO
CH3
CH2
H3C
NH2
NH2
HCl
Cl
H3C
NH3
+ Cl
10
12
13
14
The reason for the increased acidity of 2,2,2trifluoroethanol is that the three electronegative
fluorine atoms stabilize the negatively charged
conjugate base.
15
16
17
19
21
Figure 2.5
Summary of the factors that
determine acidity
22
ka=
pka=
CH3
10-10
10-41
10
41
OH
23
pka= 50
OH
CH3
H2O
15.7
24
Cl
pka=
25
35
-7
Both acetylene and hydrogen will work
(must have higher pka)
Not using pka, which is the stronger acid?
H2S
HBr
OR
Cl2CH2COOH
27
28
29
30
31
32
electrophile
nucleophile
33
34
35
36
37
CH
B
Br
Br
38
39