Sarah Ettaleb

Fortune Ebinumolise

Experiment Performed Date:

January22nd 2016 from 8:30 to 11:30
Due Date: January 26th, 2016

Experiment 1: Introduction to Organic Chemistry Laboratory

References:

202-DCP-05 Organic Chemistry I

PostLab
Objective(s): (Briefly state the experimental goals of the experiment.)
1) Determine the melting point of acetanilide and understand the theory of
intermolecular forces involved. Also, understand how the melting point apparatus
works.
2) Use Thin Layer Chromatography on acetanilide with different eluents and be able to
understand its behaviour based on its chemical structure and intermolecular forces.
Description and Observed Physical Properties of acetanilide
Formula

C8H9NO

Structure

Literature mp

114.3C

Experimental
mp

114.7 C 115.7 C

Color and
crystalline
shape

White to Gray
solid
White shinning
crystalline
scales/leaflets.

*Reference: "Acetanilide." Acetanilide. U.S National Library of Medicine, Web. 23 Jan. 2016.
<https://pubchem.ncbi.nlm.nih.gov/compound/acetanilide#section=Top>
Question 1: Explain why taking a melting point helps you identify an unknown.
The melting point is a characteristic, physical property of a pure solid. Therefore, each
unique pure solid has its own specific melting point raneg. Thus, by knowing the melting point
range of an unknown pure solid and comparing it to known literature values the solid can be
identified.
Question 2: What are the effects of an impurity on a melting point? (two effects)
Impurities can affect the melting point of a substance by disrupting its lattice structure.
Firstly, impurities within the solid typically cause a decrease in the melting point. Secondly,
impurities can also broaden the range of the melting point causing the range to increase. For
example, if the literature value of a pure solid is 112C. The impurities would decrease the
melting point and increase the range so it could be 97C - 111C.
Question 3: Explain briefly how taking a melting point helps you determine the purity of a
compound.
Impurities within the solid can interfere with the organization of the structure of the solid
since they cannot fit correctly with the compound. This weakens the structure of the solid

causing it to melt more easily. Therefore, impurities decrease the melting point of a compound.
Consequently, by decreasing the melting point, this widens the range of the melting point.
Therefore, the wider the melting point range the more impure the compound and vice versa.
Question 4: What effect would incomplete drying of a sample (for example, the incomplete
removal of a recrystallization solvent) has on the melting point?
Soluble substances can affect the melting point of a solid. This is because they can
interfere with the structure of the solid. Thus, the incomplete removal of a recrystallizing solvent
is soluble in the substance and can act as an impurity. As mentioned above, impurities can
decrease and broaden the range of the melting point of the solid.
Question 5: Why should the melting point sample be finely powdered?
If the sample where to not be a powder but rather coarse pieces of solid, unequal melting
could occur. Since the outside of the solid is closer in contact with heat than the inside, it would
melt first and the inside would melt afterwards since heat takes time to propagate to the inside.
This could render the melting point of the solid more ambiguous. To prevent unequal melting,
the solid can be finely powdered to maximize the distribution of heat towards the solid particles.
Also finely grounding the solid would decrease the amount of air pockets that are found
within the sample. Air can absorb heat energy therefore, it can increase the melting point of the
solid.
Question 6: Why is it important to heat the melting point bath slowly and steadily when the
temperature gets close to the melting point?
To ensure accurate readings of the melting point it is best to melt the sample slowly. It
takes time for heat energy to disrupt the intermolecular forces of the sample. Therefore, if the
temperature is increased rapidly the sample will not have enough time to absorb the energy as
rapidly as the increase in temperature. Therefore, this would cause the melting point range to
increase. Therefore, it is best to bath slowly so that the solid could absorb the energy as the
temperature increases.
Question 7: Why is it important to pack the sample tightly in the melting point capillary?
It is important to pack it tightly in order to minimize the presence of air pockets. Air can
also absorb energy and slow the transfer of heat. Therefore, it can cause the whole sample to
absorb more energy than required. This would indicate that the melting point range would be
slightly higher which is unwanted.
Question 8: a. Discuss the chemical structure of the acetanilidine, and analyze its
intermolecular forces (=IMF) based on the structure you drew. Is acetanilide polar,
partially polar, can it form H bonds etc.
Acetanilide is polar and has dipole- dipole interactions because it contains
asymmetric polar bonds of C-O, N-H and N-C. Acetanilide also contains hydrogen
bonds because it contains a hydrogen bonded to a nitrogen with a lone pair. This
satisfies the condition of hydrogen bonding which are among the strongest

intermolecular forces. As with any molecule, acetanilide also contains London

dispersion forces. Based on its structure, acetanilide is expected to dissolve into
solvents with similar intermolecular forces.
b. Use the Rf values that you obtained to rank the advance of acetanilide on the
silica with the different eluents. Does the ranking you obtained make sense?
Explain, based on structure and IMF. 7
Question 9: The Rf value of compound A is 0.34 when the TLC plate is developed in
hexane and 0.44 when the plate is developed in diethyl ether. Compound B has an
Rf value of 0.42 in hexane and 0.60 in diethyl ether. Which solvent would give a
better resolution? (=be better for separating a mixture of A and B by TLC) Explain
When comparing the two compounds, it can be concluded that compound b is

Discussion
One of the issues that occurred in the lab was how the TLC plates were spotted. The dot
samples that were placed on the plates contained too much acetanilide and when the sample was
viewed after its travel, it was a long broadened dot. This made the calculation of the Rf difficult.
However, some samples were re-run and this time less acetanilide was placed on the TLC this
lead to a smaller more compact dot in the end. This facilitated the calculation of the Rf. Below
are the TLC plates that contained too much acetanilide:

*These were re-run and placed into the post lab section of the report
However, to improve an even smaller amount of acetanilide could have been placed on the TLC
plates. Alternatively, the acetanilide could have been diluted even more with chloroform to
achieve a low concentration of it. This would create a smaller more compact finishing dot in
which measurements can easily be taken.
Another issue regarding the TLC part of the lab was the high level of the solvent that was in the
jar. For the first plate, too much solvent was added to the jar that when the TLC place entered it,
the solvent level surpassed the starting line of the TLC plate (where the spot was). This is an
issue because the solvent could dissolve the sample before it could even travel with it due to
capillary action. However, for all of the other plates the solvent level was also made sure to be
below the spots.
Another issue regarding the melting point part of the lab was how finely powdered the
acetanilide was. The acetanilide that was used as a sample was not grounded a lot with the
mortar and pestle. This important step would reduce the presence of air pockets and made the
solid more tightly packed. However, since it was not done properly it could explain the high

melting point range that was obtained in the lab. The air pockets can slow the transfer of heat to
the solid particles. This would indicate that the solid would absorb more energy than required,
which explains the higher melting point range that was obtained. To improve, next time the solid
needs to be broken down with a mortar and pestle as much as possible and needs to be tightly
packed into the capillary tube. This could have been obtained by dropping the capillary tube with
the sample into a long vertical glass tube.