Understanding the principles of organic chemistry - a laboratory course - Pedersen & Myers.pdf
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Approximate pK
a
Values for Some Organic Acids*
Acid
Base
pK
a
Acid
Base
pK
a
9.2
25
HCN
CN
SO
3
H
SO
3
O
O
10
OH
O
0.2
F
3
C
OH
F
3
C
O
O
O
10.3
O
O
O
O
HO
O
3.7
H
OH
H
O
10.3
CH
3
S
CH
3
SH
4
NH
3
NH
2
O
O
O
O
13
H
3
CH
2
CO
OCH
2
CH
3
H
3
CH
2
CO
OCH
2
CH
3
H H
H
O
O
4.2
OH
O
16
CH
3
CH
2
OH
CH
3
CH
2
O
O
O
O
O
4.8
17
OH
O
NH
2
NH
18
5.2
(CH
3
)
3
COH
(CH
3
)
3
CO
N H
N
O
O
20
O
O
H
3
C
CH
2
H
3
C
CH
3
6.4
HO
OH
HO
O
O
O
24
O
O
H
3
CH
2
CO
CH
2
H
3
CH
2
CO
CH
3
8.3
NH
N
H
O
O
40
N
N
O
O
*
Note that pK
a
values less than 22 and greater than 18 cannot be measured
in water and vary depending on the solvent used for the measurement.
O
O
9
H H
H
Common Solvents
Name
[CAS Number]
Molecular
Formula
Formula
Weight
Boiling
Point oC
Density
g/mL
Structure
acetic acid
[64-19-7]
O
C
2
H
4
O
2
60.05
116–118
1.05
OH
acetic anhydride
[108-24-7]
O
O
C
4
H
6
O
3
102.09
138–140
1.08
O
acetone
[67-64-1]
O
C
3
H
6
O
58.08
55–56
0.79
acetonitrile
[75-05-8]
C
2
H
3
N
CH
3
CN
41.05
80–81
0.79
1-butanol
[71-36-3]
C
4
H
10
O
74.12
117
0.81
OH
carbon tetrachloride
[56-23-5]
CCl
4
CCl
4
153.82
76–77
1.59
chloroform
[67-66-3]
CHCl
3
CHCl
3
119.38
60–62
1.49
dichloromethane
methylene chloride
[75-09-2]
CH
2
Cl
2
CH
2
Cl
2
84.93
39–40
1.32
diethyl ether
[60-29-7]
C
4
H
10
O
74.12
35
0.71
O
N,N
-
dimethylformamide
[68-12-2]
O
C
3
H
7
NO
73.10
152–153
0.95
H
N
dimethyl sulfoxide
[67-68-5]
O
C
2
H
6
OS
78.14
189
1.10
S
1,4-dioxane
[123-91-1]
C
4
H
8
O
2
88.11
100–101
1.03
OO
1,3-dioxolane
[646-06-0]
O
C
3
H
6
O
2
74.08
74–75
1.06
O
ethanol
[64-17-5]
C
2
H
6
O
46.07
78
0.79
OH
ethyl acetate
[141-78-6]
O
C
4
H
8
O
2
88.11
76–77
0.90
O
n
-hexane
*
[110-54-3]
C
6
H
14
86.18
68–69
0.66
methanol
[67-56-1]
CH
4
O
CH
3
OH
32.04
64–65
0.79
n
-pentane
[109-66-0]
C
5
H
12
72.15
35–36
0.63
1-propanol
[71-23-8]
C
3
H
8
O
OH
60.10
96–97
0.80
2-propanol
[67-63-0]
OH
C
3
H
8
O
60.10
80–83
0.78
tetrahydrofuran
[109-99-9]
C
4
H
8
O
72.11
65–67
0.89
O
toluene
[108-88-3]
C
7
H
8
92.14
110-111
0.87
water
[7732-18-5]
H
2
O
H
2
O
18.02
100
1.00
*
The term
hexanes
refers to a mixture of hexane isomers that has a density of 0.67.
UNDERSTANDING THE
PRINCIPLES OF ORGANIC CHEMISTRY
A LABORATORY COURSE
Steven F. Pedersen
University of California, Berkeley
Arlyn M. Myers
University of California, Berkeley
Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States
Understanding the Principles of Organic
Chemistry A Laboratory Course
Steven Pedersen and Arlyn Myers
© 2011 Brooks/Cole, Cengage Learning
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