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Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

9/8/2015
Drawer No.

Course / Section

#21

CHEM
315/204

Purpose:
The purpose of this experiment is to determine the melting point range for two known solid organic
compounds, a 1:1 mixture of the two knowns, and an unknown chemical compound, and determine the
identity of the unknown chemical compound using the Mel-Temp apparatus. Using an Abbe
refractometer, determine the refractive index of a known organic liquid, an unknown organic liquid
sample, and determine the identity of the unknown organic liquid.

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

9/8/2015
Drawer No.

Course / Section

#21

CHEM
315/204

Approach:
Determine the melting point temperature range for each of the following: each of the 2 known organic
compounds, a 1:1 mixture of the known organic compounds, and the unknown organic compound.
Determine the identity of the unknown compound based on the melting point temperature range.
Determine the refractive index for each of the following: a known organic liquid and an unknown
organic liquid. Adjust the raw refractive index values recorded to standard temperature (20oC) using
the temperature correction formula. Determine the identity of the unknown liquid based on the
adjusted refractive index value.
References
Text
Pavia, D.L., Lampman, G.M., Kriz, G.S., Engel, .G.R., 2011, Introduction to Organic Laboratory
Techniques, A Small Scale Approach, GMU Edition, Chem 315/318, Cengage Learning: pp. 643652; pp. 845-850
Slayden, S., Stalick, W., Roth, R, 2014, Organic Chemistry Laboratory Manual, 2nd Edition:
Pearson Custom Publishing: pp. 25-30
Web Site URL
Dr Schornicks Website: http:/mason.gmu.edu/~jschorni/meltpoint
Unknown Compounds
N-Phenylacetamide (Acetanilide), CAS No. 103-84-4, CRC Handbook of Chemistry & Physics, 84th
Edition, Lide, D.R., Editor-in-chief, 2003-2004, CRC Press, #18, p. 3-4.
Methylbenzene (Toluene), CAS No. 108-88-3, CRC Handbook of Chemistry & Physics, 84th Edition,
Lide, D.R., Editor-in-chief, 2003-2004, CRC Press, #10111, p. 3-514.

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

Proc # 1

Melting Point

2 known organic
solids

1:1 ratio the


known compounds

1 unknown
compound

Capillary tubes
Desc:

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Results

Materials

9/8/2015

Equipment

Compound #1: d-l mandelic acid

Mel-Temp
Apparatus

Watch glass

Spatula

Thermometer

Glass tubing

Avg(oC):
Observ:

Obtain samples of two compounds in


sequence from the list of compounds with known
melting points provided.

Using a watch glass and spatula, crush a


small amount of compound #1 to a fine powder.

Load 1-2mm of the sample by tapping it


with the open end of a capillary tube.

Gently drop the capillary tube (closed end


down) down the glass tubing to move the sample to
the closed end of the tube.

Insert the capillary tube closed end down


into the Mel-Temp device.

Gradually heat the sample increasing the


temperature approximately 2-3oC per minute to
determine the rough melting point.

Record the first M.P. when the compound


begins to melt.

Record the second M.P. to when the sample


is completely liquefied.

Record all temperature readings to one


decimal place.

Allow the sample to cool and solidify.

Heat the sample again until the temperature


is approximately 10oC below the rough melting
point.

Adjust the temperature to heat at a slower


rate (approximately 0.5oC per minute) and record a
second M.P. range.

Unk No. MP 21

1st M.P. (oC)


115.0
114.0
114.5

2nd M.P. (oC)


118.0
117.0
117.5

Fine white powder, easily


crushed. M.P. was sharp and
within a 3 degree range.

Compound #2: benzoic acid

Avg(oC):
Observ:

1st M.P. (oC)


118.0
118.0
118.0

2nd M.P. (oC)


123.0
122.0
122.5

Large white crystals, difficult to


crush. M.P. was sharp and within
a 4.5 degree range.

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

Repeat this procedure to record a second


reading for the first known

Repeat the above steps for the second


known.

Prepare an approximate 1:1 ratio of the two


known compounds.

Melt the 1:1 ratio (do not record


temperature) to form a homogeneous mixture.

Allow to cool and solidify.

Record one M.P. range measurement


repeating the appropriate steps above.

Record one M.P. range for the unknown


sample

Compare M.P. value for the unknown with


the list of knowns provided (Slayden, pp. 27).

Prepare a mixture of the known that most


closely matches the M.P. of the unknown and the
unknown compound in the same fashion as the 1:1
mixture.

Record the M.P. for this mixture to confirm


the identity of the unknown compound.

If the M.P. of the unknown mixture differs


greatly, repeat with another known to confirm the
unknowns identity.

9/8/2015
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1:1 Mix: d-l mandelic acid + benzoic acid


1st M.P. (oC)
86.0

2nd M.P. (oC)


98.0

Observ: Broadening and lowering of M.P.


range occurred as expected.

Unknown Compound: MP 21
1st M.P. (oC)
113.0

2nd M.P. (oC)


116.0

Observ: Large tanish colored flakes,


difficult to crush. Lighter color
when crushed. Appearance similar
to that of the known acetanilide.
Unknown Mix: MfP 21 + acetanilide

Equation Setup:

1st M.P. (oC)


2nd M.P. (oC)
113.0
116.0
o
Avg( C):
114.5
Observ: M.P. of the unknown was not
lowered by the addition of
acetanilide.

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

Proc # 2

Refractive index

1 known liquid
1 unknown
liquid

Desc:

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#21

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Results

Materials

9/8/2015

Equipment

Abbe
refractometer (
0.0002)

Tissue
Alcohol
Dropper

Unk No.

Room temperature: 22.3 oC


Known Liquid: acetonitrile
1st ND
2nd ND
Avg ND:

1.3441
1.3445
1.3443

Observ: Clear liquid. ND recorded was very


close to the expected value of 1.3441.

Note and record the temperature of the


room

Carefully clean the prisms of the Abbe


refractometer with a tissue moistened with
alcohol.

Add a small amount of the known


compound between the prisms.

Gently close the prisms.

Flip the switch on the left of the


instrument up to turn on the Sodium-D lamp
and adjust it into position.

Use the adjustment knob at the right of


the instrument so the crosshairs intersect with
the horizontal dividing line of the visual field.

Adjust the drum knob at the front of the


instrument to sharpen the horizontal line if
chromatic aberration occurs.

Press down on the switch on the left of


the instrument to display the refractive index
scale

Read and record the refractive index to


four decimal places.

Repeat this measurement and record a


second reading.

Repeat process using 3-4 drops of the


unknown liquid.
Equation Setup:

RI 23

Unknown Liquid: RI 23
1st ND
2nd ND
Avg ND:

1.4952
1.4955
1.4954

Observ: Clear liquid, strong odor.

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

Proc # 3

9/8/2015
Drawer No.

Course / Section

#21

CHEM
315/204

Temperature Correction Factor


Materials

Desc:

Equipment

Adjusts the measured value of the


refractive index (ND) obtained using the Abbe
refractometer to standard temperature of 20oC.

Refractive index is both wavelength and


temperature dependent for a given compound.

Temperature and density are inversely


related.

Density and the velocity of light are


inversely related.

As temperature increases, density


decreases and velocity of light increases.

Refractive index decreases as


temperature increases.
Equation Setup:
Refractive Index (n) the ratio of the velocity of
light in the air to the velocity of light in the medium
being measured (Pavia, pp845)
For temperatures >20oC add the temperature
correction factor
ND20 = NDRm Temp + (Room Temp - 20)* 0.00045
Where N represents the refractive index reading.
The superscript indicates the temperature at which
the measurement was read. The subscript indicates
the light source utilized.

Results
Room temp = 22.0 oC
Known Liquid: acetonitrile
ND20 = NDRm Temp + (Room Temp - 20)* 0.00045
ND20 = 1.3443 + (22 20) * 0.00045
ND20 = 1.3452
Observ:
Unknown Liquid: RI 23
ND20 = NDRm Temp + (Room Temp - 20)* 0.00045
ND20 = 1.4954 + (22 20) * 0.00045
ND20 = 1.4963
Observ:

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

9/8/2015
Drawer No.

Course / Section

#21

CHEM
315/204

Summary of Results:
The average melting point temperature range of known organic compound #1 (d-l mandelic acid) was
114.5-117.5 oC. The average melting point temperature range of known organic compound #2 (benzoic
acid) was 118.0-122.5 oC. The average melting point temperature range of a 1:1 ratio of the two known
compounds (d-l mandelic acid +benzoic acid) was 86.0-98.0 oC. The average melting point of unknown
compound #1 (MP 21) was 114.5 oC. The refractive index for known liquid #1 (acetonitrile) was 1.3443.
The corrected value for known liquid #1 (acetonitrile) calculated from the refractive index raw value
was 1.3452. The refractive index for unknown liquid sample #2 (RI 23) was 1.4954. The corrected
value for unknown liquid sample #2 (RI 23) calculated from the refractive index raw value was 1.4963.

Analysis & Conclusions:


In this experiment, the physical properties of melting point and refractive index were used to
determine the purity and the identity of organic compounds.
The melting point is defined as the temperature range over which a compound transitions from solid to
liquid states. This physical measurement is often used to determine the purity of a crystalline solid.
Typically the melting points of pure compounds are sharp, and occur over a 3oC temperature range. In
a mixture of more than one substance, the melting point is typically lower and occurs over a broader
range of temperatures. The only exception to this is the eutectic point, in which the melting point of a
mixture is much lower than those of its components, but occurs sharply, and can be easily mistaken as
a pure compound.
The melting point temperature range of several solid organic compounds was examined using the MelTemp device. First, the melting point was determined for two known compounds, dl-mandelic acid
and benzoic acid (114.5-117.5oC; 118.0-122.5oC on average respectively). Both compounds displayed
sharp melting points that agree closely to literature values suggesting minimal presence of impurities.
Next, to demonstrate the effect of impurities on the melting point of a compound, an approximate 1:1
ratio mixture of the two known compounds was prepared and the melting point of the mixture was
determined. The melting point temperature range of the 1:1 mix was lower and occurred over a wider
range of temperatures (86.0-98.0 oC) by comparison to the melting points of the pure compounds.
Because the mixed melting point was not sharp, it cannot be considered the eutectic point for these
compounds. It is likely that in this instance due to the structures of the two compounds, that benzoic
acid served as an impurity due to structural and solubility differences between the two compounds,
lowering the melting point below that of dl-mandelic acid.
Finally, the melting point was used to determine the identity of unknown organic solid MP 21. The
melting point was 113.0-116.0oC, which matched closely to the literature value for acetanilide given on
the list of known compounds provided. To strengthen this argument, upon visual assessment of the

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

9/8/2015
Drawer No.

Course / Section

#21

CHEM
315/204

two compounds, both the unknown and the suspected compound were similar in color, appearance and
hardness. To verify the identity of the unknown, an approximate 1:1 mix of the unknown and the
suspected organic compound was prepared. The mixed melting point did not display broadening or
lowering, suggesting that when added to unknown MP 21, acetanilide did not act as an impurity,
confirming the identity of the unknown.
In measuring the melting point of unknown MP 21 and the unknown mix, the melting points recorded
were identical, suggesting the initial and final temperature readings were observed and recorded
precisely. One factor that could introduce error in determining the melting point is heating the
compound too rapidly, or increasing the voltage abruptly during the melting process. An abrupt
increase can cause a discrepancy between the temperature that the thermometer reads and the actual
temperature of the compound, resulting in a less precise measurement. It is best to increase the
temperature of the sample gradually at a moderate voltage to ensure the most precise reading.
Refractive index is a unitless ratio of the speed light travels in a vacuum to the speed light travels
through a substance. The magnitude of refractive index measurements is affected by two factors:
temperature and the wavelength of incident light on the sample. The wavelength of light used in these
measurements was yellow light at 589 nm (Sodium-D light) and was held constant because of the light
source. The temperature was also held constant at 22oC. To adjust the raw measurements to standard
temperature (20oC) the temperature correction factor calculation was used. Because the compounds
examined were not highly purified, measurements were allowed an error of 0.0002.
Using the Abbe refractometer, the refractive index of the known liquid compound acetonitrile was
determined. After adjusting the raw measurement to standard temperature (20oC) the refractive index
was 1.3452 and closely matched literature values, which suggests a relatively pure sample. Next, the
refractive index of unknown organic compound RI 23 was measured. The after adjusting the raw
measurement to standard temperature, the refractive index of the unknown was 1.4594, and most
closely matched the literature value for toluene.
Although the refractive index does not provide direct information about the structure of a compound,
it does provide some information about the polarizability of a compound. When comparing the
structure of acetonitrile (C2H3N) with that of toluene (C7H8), both the linear structure and triple bond
between carbon and nitrogen present in acetonitrile restrict bond rotation and decrease the molecules
polarizability, resulting in a lower refractive index. Conversely, toluene contains an aromatic ring
structure, increasing the molecules polarizability, resulting in a higher refractive index.
In determining the identity of unknown RI 23, the refractive index was within 0.0002 of the literature
value, suggesting that the instrument was calibrated properly. One factor that could introduce error in
determining the refractive index is not properly adjusting the instrument to remove all chromatic
aberration. Removal of chromatic aberration is a subjective visual assessment that in part relies on the
individuals visual acuity. If an individual is unable to perceive this clearly, this may result in an
incorrect refractive index value. It is recommended to have more than one individual visually asses the
sample or use multiple trials to determine the refractive index accurately.

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

9/8/2015
Drawer No.

Course / Section

#21

CHEM
315/204

Literature Summary (Unknowns, Synthesized Compounds)


Unknown No.
CAS No.

MP 21

RI 23

103-84-4

108-88-3

N-phenylacetamide

Methylbenzene

Acetanilide

Toluene

Melting Point
(oC)

Lit 114.4oC
Exp 114.5oC

Lit -95.0oC
Exp

Lit
Exp

Lit
Exp

Boiling Point
(oC)

Lit 292oC
Exp

Lit 110.6oC
Exp

Lit
Exp

Lit
Exp

Lit
Exp

1.4941
1.4963

Lit
Exp

Lit
Exp

Name (IUPAC)

Synonyms

Refractive Index Lit N/A


(nD20)
Exp
Solubility
(Rel to Water)

Lit 4g/L (20oC)


Exp

Lit 0.52g/L (20oC)


Exp

Lit
Exp

Lit
Exp

Density
Rel to Water

Lit 1.219015g/cm-3
Exp

Lit 0.862325g/cm-3
Exp

Lit
Exp

Lit
Exp

Molecular
Formula

Structural
Formula

C8H9NO

C7H8

Experiment:

Date:

Melting Point and Refractive Index


Name

Partners

Katheryn Soto

N/A

9/8/2015
Drawer No.

Course / Section

#21

CHEM
315/204