Lab 1

Melting point and boiling point of organic compounds

Objective
• To learn the techniques for determining the melting point and boiling point of organic
chemicals
• To identify the organic chemicals by the melting point and boiling point

Experiments 1: Determining the melting point of the substance by Thiele

Melting point (mp)

Melting point is one of the physical characteristic of substance.such as boiling point, molecular
weight, density and refractive index and etc. The melting point (liquefaction point) is the temperature at
which it changes state from solid to liquid at atmospheric pressure. At the melting point the solid and
liquid phase exists in equilibrium. The melting point of a substance depends on pressure and is usually
specified at standard pressure. When considered as the temperature of the reverse change from liquid to
solid, it is referred to as the freezing point or crystallization point. Because of the ability of some
substances to supercool, the freezing point is not considered as a characteristic property of a substance.
Therefore, melting point is an important physical property of a compound that can be used to identify a
substance and as an indication of its purity.

Melting point determination apparatus

A. Thomas-Hoover Uni-Melt B. Mel-Temp: Temperature Range
Temperature range 25–300 C 25–300 C
C. Fisher-Johs: Temperature range
Temperature range 25–300 C

D. Thiele: Temperature range

Temperature range 25–180 C
Reasons for determining melting points:

1. The melting point indicates the level of purity of a sample. An impure compound melts over a
wider range of temperatures, usually greater than 2 degrees.
2. The melting point helps to identify unknown samples, narrowing the number of possibilities,
because a pure solid melts reproducibly over a narrow range of temperatures.

In this lab, the identity of an unknown organic compound will be determined by comparing its
experimental melting point to those of a variety of known compounds.

Procedure:

1. Obtain a capillary melting point tube and a known compound. The known compound may need
to be ground into a fine powder with a spatula and watch glass.
2. Load the grounded sample into the capillary tube approximately 1–2 mm height of sample in
the tube (Larger samples will heat unevenly).
3. Packing the powder sample to the bottom capillary tube by dropping the capillary tube
perpendicular to the table (through a glass funnel); the capillary tube will bounce on the table.
Repeat the dropping until the powder is well packed
4. Tight the capillary melting point tube with the thermometer and place in the Thiele-tube
containing paraffin oil as shown in the picture above (be demonstrated in the lab).
5. Slowly heat up (to acquire the most accurate results) the paraffin oil in the Thiele-tube (at the
arm). The sample should be observed continuously, so that the melting point of the sample is not
missed.
6. Record the melting range, which begins when the sample first starts to melt and ends when the
sample is completely melted.
7. Compare the melting temperature from the experiment in the Table 1, on the following page.
The known sample should melt within the range found in Table 1.
8. Predict and verify the unknown by mixing the unknown sample 1/1 ratio with the known (as
predicted) and perform the experiment to determine the melting point of the mixture. The
Thiele-tube must be cool down cool to about 50ºC before performing the experiment)
Table 1: Melting point of some substances

Substance m.p. oC
Bipheny 68-70
Naphthalene 79-82
Oxalic acid 100-102
Acetanilide 114
Benzoic acid 121
Malic acid 129-131
Urea 132
Anthranilic acid 146
Adipic acid 152
Salicylic acid 159
Hydroquinone acid 170
Anthracene 216

Experiments 2: Determining the boiling point of the substance by Thiele

Boiling Points (bp)

The boiling point of a liquid varies depending upon the surrounding environmental pressure. A
liquid in a partial vacuum has a lower boiling point than when that liquid is at atmospheric pressure. A
liquid at high pressure has a higher boiling point than when that liquid is at atmospheric pressure. For
example, water boils at 100 °C (212 °F) at sea level, but at 93.4 °C (200.1 °F) at 2,000 metres (6,600 ft)
altitude. For a given pressure, different liquids will boil at different temperatures.
The normal boiling point (also called the atmospheric boiling point or the atmospheric pressure
boiling point) of a liquid is the special case in which the vapor pressure of the liquid equals the defined
atmospheric pressure at sea level, 1 atmosphere.[3][4] At that temperature, the vapor pressure of the
liquid becomes sufficient to overcome atmospheric pressure and allow bubbles of vapor to form inside
the bulk of the liquid. The standard boiling point has been defined by IUPAC since 1982 as the
temperature at which boiling occurs under a pressure of 1 bar.[5]
The heat of vaporization is the energy required to transform a given quantity (a mol, kg, pound,
etc.) of a substance from a liquid into a gas at a given pressure (often atmospheric pressure).
Liquids may change to a vapor at temperatures below their boiling points through the process
of evaporation. Evaporation is a surface phenomenon in which molecules located near the liquid's edge,
not contained by enough liquid pressure on that side, escape into the surroundings as vapor. On the
other hand, boiling is a process in which molecules anywhere in the liquid escape, resulting in the
formation of vapor bubbles within the liquid.
 Typically, the boiling point of most liquids is reduced by about 0.5 degrees Celsius when the
atmospheric pressure drops by10 millimeters of mercury. The impure liquids have lower vapor
pressure, higher and broader range boiling point than pure liquids. Therefore, the boiling point of the
substance is used to identify and determine purity of the substance. But there are exceptions, some
liquids combine with other liquids will give a constant boiling point called “a constant boiling mixture”.
Determination of the boiling point of the loquid can be done in two ways I). If there is enough
liquid can be done by distillation, the boiling point of the substance is the temperature of the substance
that began to distill. Which is discussed. And experiment in the third experiment. II). If there is small
amount of sample, the boiling point canbe determined by the micro method using Thiele tube as shown
in the picture below.

Procedure:

1. Practicing by using absolute ethyl alcohol as a sample: set the apparatus comprising
thermometer, capillary tube, a 5 mm glass tube same as the picture below.
2. Load the liquid sample into the 5 mm glass test tube about 1 centimeter or 2 third of the height
of the tube.
3. Place the apparatus in the Thiele tube same way as the experiment 1.
4. Slowly heat up the paraffin oil in the Thiele-tube (at the arm).
5. Record temperature and stop heating when the gas continuously bubbling out from the capillary
tube.
6. Record the temperature again when the liquid at the tip of the capillary stop bubbling.
7. Compare the observed boiling temperature with the information in the Table 2. If the reading
suggest that the sample is ethyl alcohol (indicating that you have a good skill to determine the
boiling point of the unknown liquid)
8. Perform the experiment to determine the boiling point of the unknown, in order to identify the
unknown.
9. Answer the report by choosing two possible compounds
The apparatus for determining boiling point by the micro method

Table 2: Boiling Point of Some Substances at 1 atmospheric pressure (1atm)

Substances b.p. oC
Choroform 61
Methyl alcohol 65
n-Hexane 69
Ethyl acetate 77
Ethyl alcohol 78.1
Cyclohexane 81
Isopropyl alcohol 82
Ethylene chloride 84
n-Propyl alcohol 97
n-Heptane 98
Dioxane 101
Toluene 111
n-Butyl alcohol 117
Xylene (o, m or p) 139-142
Tetrachloroethane 146.3
Questions

1. .How to verify purity of the crystalline substance?

2. If the melting point of the solid sample is 121-122 degrees Celsius. How can we confirm that
the sample is benzoic acid with a melting point of 121-122 ° C ?
3. In the boiling point determination experiment, Why the boiling point is the temperature that the
liquid.the liquid stop bubbling and the liquid starts to flow into the capillary tube?
 Lab 1
Melting point and boiling point of organic compounds

Name ............................................................................. ID ................................. Group .............................

Lab partner ..............................................................ID .....................................................................

Lab partner ..............................................................ID .....................................................................

Instructor .................................................................Date ..................................................................

Experiment 1: Determining the melting point of the organic compounds

Sample number ...............

Initial melting temperature..............................C

Completely melt temperature ......................... C

The melting point of the sample .................... C

Possibility, the unknown sample is

1. ...........................................................................................

2. ...........................................................................................

Mix unknow sample with predict compound 1 Compound 2

Initial melting temperature.................................C Initial melting temperature................................C

Completely melt temperature ............................ C Completely melt temperature ............................ C

The melting point of the sample ....................... C The melting point of the sample ..........................C

Conclusion, the unknown is .......................................................................................................................

..........................................................................................................................................................................
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Experiment 2: Determining the boiling point of the organic compound by a micro method

Practicing: absolute ethyl alcohol

Initial bubbling temperature...........................................C

Stop bumbling temperature .......................................... C

The melting point of the sample .................................. C

Boiling point of absolute ethyl alcohol ........................ C

Unknown luquid: Sample number ………………………

Initial bubbling temperature...........................................C

Stop bumbling temperature .......................................... C

The melting point of the sample .................................. C

Boiling point of the unknown ...…….......................... C

From the Table 2, the unknown sample is

1. ...........................................................................................

2. ...........................................................................................

Conclusion and Discussion

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 Questions

1. .How to verify purity of the crystalline substance?

Answer

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2. . If the melting point of the solid sample is 121-122 degrees Celsius. How can we confirm that the
sample is benzoic acid with a melting point of 121-122 ° C ?
Answer

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3. In the boiling point determination experiment, Why the boiling point is the temperature that the
Answer

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