Melting Point of Organic Compounds

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FACULTY OF APPLIED SCIENCES

KUALA LUMPUR CAMPUS


Semester: ​[ ] May [ / ] September [ ] January (​please tick “​✓​”)
Academic Year: 2019​
Course Code & Title: AACB 3133 CHEMISTRY OF ELEMENTS AND ORGANIC
COMPOUNDS
Programme: Diploma in Science (Chemistry and Biology )
Student’s Name (Registration Number): 1. Wong Pui Mun (18WLD03931)
2. Chin Jia Yue (18WLD03979)
Submission Date:

Declaration
We confirm that we have read and shall comply with all the terms and condition of
TAR College’s plagiarism policy.
We declare that this assignment is free from all forms of plagiarism and for all intents
and purposes is our own properly derived work.

Signature(s):_____________________________________________________________

Name(s):_________________________________________________________________

Date: ___________________
Experiment 1
Title: Melting Point of Organic Compounds

Objectives:
1. To study the melting points of the compounds before and after mixing;
2. To determine the identity of unknown by comparing the melting points of other
substances;

Introduction:
Melting point is the temperature at which a substance starts to turn from solid into liquid
phase. The particles of a solid are packed tightly together in an orderly arrangement, their
motions are restricted which can only vibrate about a fixed point. As the solid is heated, the
particles received kinetic energy to vibrate more vigorously until the attractive forces between
those particles starts to break. Therefore, the melting point of a solid is dependent on the
strength of those attractive forces. The stronger the forces between the particles in a solid, the
higher the energy needed to overcome the attractive forces, the higher the melting point. For
example, sodium chloride (NaCl) is an ionic compound that bonded by strong ionic bonds,
which melts at 801°C, whereas ice ( H 2 O ) is a molecular compound which are held together
by hydrogen bonds, its melting point is 0 °C. The ionic bonding is much stronger than
hydrogen bond, which is only an intermolecular forces, thus the melting point of NaCl is much
higher than the melting point of ice.
The melting point is vary for different pure substance due to the differences of their bonding
and composition. This is why the melting point can help to identify a pure substance as it is a
fixed point for every pure substance. For instance, the melting point for pure water (ice) is
exactly 0​°C. However, if the substance is mixed with another, then its melting point will be
lowered by the impurities. This process called melting point depression (Ryan, 2005).
Different substances in a mixture will actually melts at different temperatures. Thus, a pure
substance has a sharp melting point (melts at one temperature) but a mixture melts over a range
of temperatures. If salts are added into water, the melting point of the water will no longer ​0
°C. It may solidifies at between -5 °C and -20 °C (Bradley & Winterbottom, 2001). That is
how salt is added to make freezing mixtures to keep ice cream frozen.
In this experiment, the melting points of two different substances were determined by using
the melting point apparatus. Then, these two substances were mixed in different composition
to check how a substance lowers the melting point of another. In the second part, the list of the
melting points of different compounds were provided. An unknown is prepared which is
actually the same substance with one of the compounds. The identity of the unknown is also
known by checking its melting point. After that, the unknown would be mixed with the
compound which has the same melting point with it. If the melting point do not drop, then they
are the same substances; if the melting point drops, then they are different.
Procedure:
A) Melting points of known compounds and mixture:
The highest temperature of melting point apparatus was set at 17​0 °C. A quantity of
benzoic acid (solid) were put into a capillary tube and inserted into the melting point
apparatus. The melting point apparatus was started and the temperature began to rise.
The apparatus was stopped until the benzoic acid started to melt. The temperature was
recorded as its melting point. The experiment was repeated with similar quantity of
urea, a mixture of 10 mole percent benzoic acid with 90 mole percent urea, and a
mixture of 90 mole percent benzoic acid with 10 mole percent urea.

B) Identification of an unknown compound by the mixed melting point method:


Unknown is taken into the capillary tube and the melting point was checked by
inserting the capillary tube into the melting point apparatus. The apparatus was started
and the temperature began to rise. The apparatus was stopped just after the compound
started to melt. The melting point was recorded and compared to the list to estimate its
identity. The unknown was then mixed with the compound that has the same melting
point with it, both were in similar quantity. The melting point of this mixture is tested
and recorded. The melting point of the unknown should be measured again if its
melting point after mixed has changed.

Table 1: Melting point of each compound.

Compound Melting point (°C)

Benzoic acid 120-121

Benzamide 125-126

o-Benzoylbenzoic acid 126-127

Benzoin 132-133

Cinnamic acid 132-133

Salicylic acid 155-157

p-Hydroxydiphenyl 164-165

p-Bromoacetanilide 165-167

Urea 132-133

Acetylsalicylic acid 135-136

Anthranilic acid 143-144


Benzilic acid 150-151

Adipic acid 151-153

Results:

(A) ​Melting points of known compounds and mixture


Table 2: Melting points of known compounds and mixture

Compounds Melting points (°C)

Benzoic acid 122

Urea 121

10 mole percent benzoic acid and 90 mole 125


percent urea

90 mole percent benzoic acid and 10 mole 77


percent urea

(B) Identification of an unknown compound by the mixed melting point method


The melting point of the unknown compound is at 157°C. Based on the table 1 above that
shown the melting point of different compounds, it gives the information that salicylic acid has
a melting point between 155-157°C. Thus, the unknown compound is believed that it is
salicylic acid due to it has the nearest value of melting point with it.

Discussion:
From the part A experiment, the table 2 has shown that the melting point of benzoic acid is
122°C whereas urea has a melting point of 121°C. However when 10 mole percent benzoic
acid and 90 mole percent urea are mixed together. The melting point that obtained was 125°C.
Obviously, the temperature has increased. On the other hand, when 90 mole percent of benzoic
acid was mixed with 10 mole percent urea, the temperature decreased which became 77°C.
This has shown that the melting point of the mixed substance is largely differ from the melting
point of both of the substances when they are tested individually. This is due to the reason that,
one of th​e compounds has acted as an impurity toward the other and they are not the same
compound. ​Normally, the melting point of pure compound should be higher than the impure
one, because the impurities messes up of the crystalline lattice by blocking their formation and
creates irregularities. Thus the intermolecular bonds become weaker, resulting in lower heat
energy required to break the bond, making the melting point becomes lower (​Donald L. Pavia,
2016)​.
Based on the result of ​identification of an unknown compound, the melting point obtained
from the experiment is 157°C. Refer to table 1 that gives information of melting point of
different compound, it is suspected that the unknown compound is salicylic acid. To ensure
that the unknown is salicylic acid, the unknown compound was again mix with the suspected
compound with the same amount. Finally, we obtain 157°C of its melting point. It shown they
ate the same compound. If they are not the same, ​the melting point of the mixture is lower than
either of the two pure components and the melting range is large. This is because the two
compounds are different with the result that one is an impurity in the other.

Conclusion:
I​ n conclusion, mixing the unknown is believed to be the salicylic acid due to it has the same
melting point with the melting point of a mixture of the pure compound and the unknown.
Mixture melting point is useful in determining the identity of your unknown compound as if
the melting point of the mixture is the same as that of the known compound, then the known
and the unknown are most likely identical. A decrease in melting point of the mixture and a
broadening of the melting point range indicates that the compounds are different.

References:

1. Bradley I., Winterbottom M. (2001). ​The Heinemann Science Scheme: Book 2, Book 2.​
Heinemann Educational Publishers, Oxford.
2. Donald L. Pavia. (2016). ​A Microscale Approach to Organic Laboratory Techniques,
sixth edition,​ Cengage Learning, United States.
3. Ryan L. (2005).​ Scientifica : kids in lab coats. 8​. Nelson Thornes, Cheltenham.

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