Boiling Point, Melting Point, Density

CH221 Lab
12 February 2008

Introduction

The primary objective of this experiment was to study the properties of alkanes and
alcohols in terms of their boiling points and melting points. Using this information, the
composition of an unknown compound can be determined by calculating its melting point,
boiling point, and density.
Melting point is the temperature at which a crystal starts to melt until the temperature at
which the crystal disappears entirely. It is one chemical property that can be used to determine
unknowns. If the melting range is less than 2C, then the substance being tested is considered to
be pure. The more impure a substance is, the lower the boiling point is and the wider the melting
range is. There are several different factors which can determine the melting point of a
compound: symmetry, molecular weight, and intermolecular forces of attraction.
The more symmetrical a compound is, the higher its boiling point is. For example, 2,2,3-
trimethylpentane has a higher melting point than nonane. The branching of the methyl groups on
the pentane make it more symmetrical than a straight chain of carbons and hydrogens.
The greater the molecular weight of a compound, the higher the melting point is. For
example, C
20
H
42
has a higher melting point than C
19
H
40
. The molecular weight of C
20
H
42
is 282
g/mol, whereas the molecular weight of C
19
H
40
is only 268 g/mole/
Intermolecular forces of attraction can be broken up into three different categories:
hydrogen bonding, dipole-dipole attractions, and London dispersion forces. Of the three forces,
hydrogen bonding is the strongest due to the differences in electronegativity. Hydrogen bonding
occurs when hydrogen atoms bond with fluorine, nitrogen, or oxygen atoms, such as H
2
O.
Dipole-dipole bonds are the next strongest and it occurs between polar molecules, such as HCl.
London dispersion forces are the weakest of the three forces of attraction. They occur between
nonpolar molecules, such as CH
4.
. As the strength of the forces of attraction increases, so does
the melting point. Therefore, H
2
O has the highest melting point, followed by HCl, with CH
4
have
the lowest melting point.
Boiling point is the temperature at which the vapor pressure of the liquid equals the
environmental pressure surrounding the liquid. This chemical property is also affected by several
factors: molecular weight, intermolecular forces of attraction, and elongated symmetry.
The greater the molecular weight of a compound, the higher its boiling point will be, in
the same way as melting points. Also, as the strength of the intermolecular forces of attraction
increases, the boiling point of a compound will also increase.
Elongated symmetry is the length of a chain. The longer the chain is, the higher the
boiling point. For example, C
7
H
16
has a lower boiling point than C
8
H
18
because it is not as
elongated as the second compound.
Alkanes, compounds made up of the formula C
n
H
2n+2
, are made up of only carbon and
hydrogen atoms. Alcohols are compounds bearing the functional group OH. As a result, alkanes
have lower boiling points and melting points than alcohols due to the hydrogen bonding in
alcohols. The compounds used in this experiment for melting point were the alkanes tricosane
(C
23
H
48
), tetracosane (C
24
H
50
), and pentacosane (C
25
H
52
); and the alcohols hexadecanol
(C
16
H
32
0) and octadecanol (C
18
H
38
0). The compounds used in this experiment for boiling point
were the straight chain alkane heptane (C
7
H
16
), the branched alkane 3-methylpentane (C
6
H
14
),
and the alcohol 1-propanol (C
3
H
7
O).
Density is the mass per unit volume of a substance, usually measured in g/mL. Density is
a physical property used to identify unknowns as well as melting point and boiling point.

Procedure

Melting Point (The following procedure was repeated to test the melting points of
tricosane, tetracosane, pentacosane, hexadecanol, and octadecanol.)

Small amounts of solid compound were collected in the open end of a capillary tube and
tapped to the closed end. The compound tube was placed in the MelTemp at approximately
40C. The temperature at the first sign of melting and the temperature when the compound was
completely melted were recorded. The MelTemp was allowed to cool between the testing of each
compound. See Table 1 for results.

Boiling Point (The following procedure was repeated to test the boiling points of heptane,
3-methylpentane, 1-propanol, and the unknown.)

The sand bath was set up according to the manual. Approximately 0.3mL of the
compound being tested and a few boiling chips were heated in the sand bath. The temperature
increased and leveled off. At each plateau, the test tube was pushed deeper in the sand to make
the temperature rise again. When the temperature didnt change anymore, the boiling point was
reached. Each boiling point for each compound was recorded. See Table2 for results.

Density

The mass of a test tube and 10mL Erlenmeyer flask was recorded. Approximately 0.5mL
of unknown was transferred to the test tube and the mass of the test tube, flask, and unknown
was recorded. The density of the unknown was calculated to help determine what compound the
unknown was. See Table 3 for results.

Results and Discussions


Compound Melting Range
Tricosane (49-50C)
Tetracosane (50-52C)
Pentacosane (53-54C)
Hexadecanol (48-50C)
Octadecanol (58-60C)
Table 1. Melting Points

Compound Boiling Point
Heptane 99C
3-methylpentane 64C
1-propanol 96C
Unknown 97C
Table 2. Boiling Points

Mass of test tube and 10 mL flask 20.533 g
Mass of test tube, 10 mL flask, and unknown 20.929 g
Mass of 0.5 mL unknown 0.396 g
Density of unknown 0.792 g/mL
Table 3. Density

Mass of unknown calculations:
Mass of test tube and 10 mL flask 20.533g
-Mass of test tube, 10 mL flask, unknown -20.929 g
0.396 g
Density of unknown calculations:
Mass of 0.5 mL unknown 0.396 g = 0.792 g/mL
Volume of unknown 0.5 mL

Compound Experimental Group Results
nonadecane (C
19
H
40
) 31.5-32.5, 29-31, 31-32, 33-34, 30-32, 30-32
eicosane (C
20
H
42
) 34-35, 36-38.5, 37-40,30-37, 39-41, 37-38, 35-39
heneicosane (C
21
H
44
) 38-40, 40-41, 40-42, 38-43,37-39, 41-41.25, 40-42, 40.5-42
docosane (C
22
H
46
) 42-43, 43-46, 43-45, 44-45, 44-46, 44-45, 44.0-45, 43-45
tricosane (C
23
H
48
) 47-47.8, 50-51, 45-47, 47-49, 49-50, 49-51, 46-48, 47.5-48
tetracosane (C
24
H
50
) 50-52, 49-53, 49-51, 52-54, 50-52, 51.5-52
pentacosane (C
25
H
52
) 52-54, 54-56, 49-55, 53-54, 54-55, 54-55, 54-55.5
hexacosane (C
26
H
54
) 57-58, 57-58
octacosane (C
28
H
58
) 60-60, 59-62, 58-61, 57-60, 57-60
Table 4. Class Data Melting Point of Alkanes

Compound Experimental Group Results
hexadecanol (C
16
H
34
O) 49-50, 52-53, 50-53, 48-50,50-51, 47-49, 49-50, 50-50.5
octadecanol (C
18
H
38
O) 57.5-58, 59-60, 56-58, 58-60,57-58, 57-60, 57-59, 58-59
eicosanol (C
20
H
42
O) 64-65, 64-66. 65-67, 36.5-38, 67-69, 64, 64-65
docosanol (C
22
H
46
O) 69-71, 68-70, 49-54, 67-74, 68-73, 70-71, 71-72
hexacosanol (C
26
H
54
O) 77-78, 78-80, 78-81, 77.5-79.5, 78-79, 78-79, 78-79, 79-80
Table 5. Class Data Melting Point of Alcohols

Compound Experimental Group results
pentane(C
5
H
12
) 38, 36, 38, 35, 37
hexane (C
6
H
14
) 68, 67, 67
heptane (C
7
H
16
) 99, 99, 99
octane (C
8
H
18
) 129, 125
nonane (C
9
H
20
) 152, 152
decane (C
10
H
22
) 177, 177
dodecane (C
12
H
26
) 218
Table 6. Class Data Boiling Point of Straight Chain Alkanes
Compound Experimental Group results
2,2,4-trimethylpentane(C
8
H
18
) 99, 95,102, 100, 100
2,2-dimethylbutane(C
6
H
14
) 49, 49, 50, 50, 50
3-methylpentane(C
6
H
14
) 64, 69
2,4-dimethylhexane(C
8
H
18
) 111, 112, 107
2- methylheptane (C
8
H
18
) 120, 121, 118
Table 7. Class Data Boiling Point of Branched Alkanes
Compound Experimental Group results
methanol (CH
3
OH) 66, 65, 69, 66, 65
ethanol (C
2
H
5
OH) 78, 78, 79, 79
1-propanol (C
3
H
7
OH) 94, 96
1-butanol (C
4
H
9
OH) 120, 118, 104, 112
1-pentanol (C
5
H
11
OH) 138, 138
1-hexanol (C
6
H
13
OH) 158
Table 8. Class Data Boiling Point of Alcohols

To construct the graph of the melting points of the class data, each individual melting range was
averaged and then those averages were averaged.

Compound Average Melting Point
nonadecane (C
19
H
40
) 31.5
eicosane (C
20
H
42
) 36.9
heneicosane (C
21
H
44
) 40.3
docosane (C
22
H
46
) 44.2
tricosane (C
23
H
48
) 48.3
tetracosane (C
24
H
50
) 51.3
pentacosane (C
25
H
52
) 53.9
hexacosane (C
26
H
54
) 57.5
octacosane (C
28
H
58
) 59.4
See Graph 1 for this data
Compound Average Melting Point
hexadecanol (C
16
H
34
O) 50.1
octadecanol (C
18
H
38
O) 58.2
eicosanol (C
20
H
42
O) 61.3***
docosanol (C
22
H
46
O) 67.6***
hexacosanol (C
26
H
54
O) 78.7
See Graph 1 for this data

To construct a graph of the boiling points of the class data, all boiling points for each compound
were averaged.

Compound Average Boiling Point
pentane(C
5
H
12
) 36.8
hexane (C
6
H
14
) 67.3
heptane (C
7
H
16
) 99
octane (C
8
H
18
) 127
nonane (C
9
H
20
) 152
decane (C
10
H
22
) 177
dodecane (C
12
H
26
) 218
See Graph 2 for this data

Compound Average Boiling Point
2,2,4-trimethylpentane(C
8
H
18
) 99.2
2,2-dimethylbutane(C
6
H
14
) 49.6
3-methylpentane(C
6
H
14
) 66.5
2,4-dimethylhexane(C
8
H
18
) 110
2- methylheptane (C
8
H
18
) 119.7
See Graph 2 for this data

Compound Average Boiling Point
methanol (CH
3
OH) 66.2
ethanol (C
2
H
5
OH) 78.5
1-propanol (C
3
H
7
OH) 95
1-butanol (C
4
H
9
OH) 113.5
1-pentanol (C
5
H
11
OH) 138
1-hexanol (C
6
H
13
OH) 158
See Graph 2 for this data

The graph of the melting points for the class data is seemingly normal, but the alcohols
were off. Particularly eicosanol (C
20
H
42
O) and docosanol (C
22
H
46
O). For the most part, the
class collected melting ranges that were close to each other, but one set of data for each was very
far off, thus altering the cumulative average. There were no such problems in the graph and
averages of the boiling points of the class data. The only problem was the uneven number of tests
run for each compound. Some compounds underwent as many as 8 tests, while others ran
through only once. Another source of error comes from being too dependent on other groups
information. It leads to inaccuracy in the graphs, as evidenced in the melting point data.

Conclusion

The unknown boiling point compound was determined to be 1-propanol when compared
to the boiling points and molecular weights on Graph 2. The boiling point of the unknown was
97C and it nearly matched up to the 95 boiling point of 1-propanol, which is an alcohol.
However, the unknown may also have been heptane, a straight chain alkane with a boiling point
of 99C.