Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204

Purpose:
The purpose of this experiment is to determine the identity of an unknown organic compound via
simple distillation, IR and Mass spectral analysis, and analysis of various physical properties.

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204

Approach:
Determine rough boiling point and purify unknown compound via simple distillation. Describe
physical properties of unknown sample. Determine the relative density of the unknown sample in
comparison to H2O and the solubility of the compound in H2O. Determine the refractive index of the
unknown compound using the Abbe Refractometer. Adjust the refractive index using the temperature
correction factor. Obtain IR and Mass spectrums for the unknown compound to determine its
molecular structure and molecular weight.
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.571578; pp.709-710; pp.719-726; pp. 851-886; pp 941-959
Slayden, S., Stalick, W., Roth, R, 2014, Organic Chemistry Laboratory Manual, 2nd Edition:
Pearson Custom Publishing: pp. 35-46
Solomons, T.W.G., Fryhle, C.B., Snyder, S.A., 2014, Organic Chemistry, 11th Edition: John Wiley &
Sons Incorporated: pp.86-103
Web Site URL
Dr Schornicks Website
o http:/mason.gmu.edu/~jschorni/irlecture
o http:/mason.gmu.edu/~jschorni/irspectroscopy
Unknown or Synthesized Compound
2-propanone (acetone) , CAS No. 67-64-1, CRC Handbook of Chemistry & Physics, 84th Edition,
Lide, D.R., Editor-in-chief, 2003-2004, CRC Press, #33, 3-4

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

Proc # 1

Simple Distillation
Materials

Corundum or
Teflon boiling chip

Ice water bath

Unknown
organic sample

Results

Drawer No.

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#21

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Unk No.

Equipment

25 or 50mL
distillation flask

Thermomet
er

Thermomet
er adapter

Condenser

Aluminum
plate

Sand

Hot plate

Spring
clamp

Water
jacket condenser

Vacuum
adapter

50mL
Erlenmeyer flask

50mL
beaker

Tin foil

Desc:

10/20/15

Assemble the distillation apparatus (see

diagram).
Wrap
Insert a corundum or Teflon boiling chip
into the flask.
Turn on the water to begin flow through
the condenser.
Place the 50mL beaker into an ice water
bath to collect waste water containing low
boiling contaminants.
Place the unknown sample into the
distillation flask.

Temp when distillate formed

Temp when pure sample collected
Temp before rise
B.P. Range

22oC
53 oC
56 oC
53-56 oC

Observations:

Unknown organic liquid compound was

clear, free flowing, and had a strong aroma
similar to nail polish remover.

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

Gently heat the sample until vapor

begins to appear in the condenser.
Record the temperature when distillate
begins to flow into the sink.
Continue to collect distillate until the
temperature levels off.
Replace the waste beaker with the 50mL
Erlenmeyer flask.
Note the temperature, as the purified
sample is now being collected.
Collect sample until the temperature
rises.
Record the temperature as it begins to
rise.
Dispense purified sample into labeled
vial.

Equation Setup:

10/20/15
Drawer No.

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#21

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315/204

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

Proc # 2

Solubility/Density

2mL Distilled
H2O

Equipment

Medium
test tube

4-5 drops
unknown
Desc:

Add 2mL of H2O to the test tube.

Add 4-5 drops of the unknown
compound.
Agitate the mixture by shaking.
Record observations of the unknowns
solubility.

Equation Setup:

Drawer No.

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Results

Materials

10/20/15

Observations:

Unknown organic liquid compound was

miscible with water after agitation.

The unknown collected slightly at the top

of the vial after settling.

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

Proc # 3

Refractive index

1 unknown
organic compound

Tissue

Alcohol

Dropper

Equipment

Abbe
refractometer (
0.0002)

Desc:

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:

Drawer No.

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Results

Materials

10/20/15

Unk No.

Room temperature: 21 oC
Unknown Liquid:
1st ND
2nd ND
Avg ND:

1.3685
1.3589
1.3587

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

Proc # 4

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.

10/20/15
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Results
Room temp = 21oC
Unknown Liquid: RI 23
ND20 = NDRm Temp + (Room Temp - 20)* 0.00045
ND20 = 1.3587 +[(21-20) x 0.00045]
ND20 = 1.3592

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

Proc # 5

IR Spectroscopy

2 NaCl plates
(salt plate

Unknown
sample

Acetone

KBR (potassium
bromide) pellet

chemwipe
Desc:

Equipment

IR
Spectrometer

Place 1-2 drops of unknown between 2

salt plates
Place salt plate sandwich in plate holder
and inset into beam slot of the IR Spectrometer.
Check with professor to make sure
background has been scanned.
Select appropriate memory location (X,
Y, or Z)
Press scan button. Make sure the
number of scans indicates 4.
Press execute button.
If absorption does not read properly,
remove salt plate and try again using a smaller
amount of the unknown sample.
Run and record a second trial
Press plot button to produce graph.
Remove cell holder and disassemble the
apparatus.
Clean the salt plate with acetone and dry
with chem wipe
Place salt plates in desiccator to dry.

Equation Setup:

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Results

Materials

10/20/15

IR Spectrum Results:

Aliphatic (saturated) C-H stretch to the

right of 3000cm-1

C=O stretch at 1715 cm-1

Single C-O stretch 1100-1300 cm-1

2 CH3 peaks at 1375 cm-1

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204

Summary of Results:
The temperature when distillate began to form was 22oC. The temperature when collection of the purified
sample began was 53oC. The temperature just before the temperature of the sample began to rise was
56oC. The bolling point range therefore for unknown #73 was 5356 oC. The raw value recorded for the
refractive index of the unknown sample was 1.3587. The adjusted refractive index calculated from the
raw refractive index value using the temperature correction factor equation was 1.3592. The molecular
weight of the unknown sample is approximately 58 g/mol. The molecular structure of the unknown
compound is C3H6O.

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204

Analysis & Conclusions:

In this experiment the identity of an unknown organic liquid compound (#73) was determined by analysis
of various physical properties including boiling point, solubility and density relative to water, refractive
index, physical appearance, molecular structure and molar mass.
Unknown #73 was a clear, free flowing, and had a strong odor similar to that of nail polish.
To determine the boiling point and purify the unknown compound, simple distillation was carried out.
Simple distillation separates liquids with boiling points less than 150oC but greater than 25oC difference
between them at 1atm. The more volatile liquid is vaporized and a less volatile, impure substance is left
behind. Pure vapors are then cooled and condensed. This cycle of vaporization and condensation allows
pure liquid compound to be collected in a separate container for identification.
Because #73 had a lower boiling point (<50oC) the pure sample was collected in a flask placed in a water
bath. Distillate containing low boiling point contaminants began to flow into the sink around 22 oC as the
solution began to boil. Pure sample began to drip from the condenser when the solution reached 53oC.
Pure sample was collected until the temperature began to rise over 56oC, suggesting that the boiling point
range of the unknown was 53-56oC.
When tested for solubility and density relative to water, #73 was miscible in water but did collect at the top
of the vial after settling, suggesting that the unknown is slightly less dense than water.
The refractive index of #73 was also measured and adjusted using the temperature correction factor
(1.3592).
To determine the molecular weight of #73, the mass spectrum for the compound was obtained and
analyzed. The mass spectrum displayed only one molecular ion peak at the far right of the spectrum with
the highest mass/charge ratio, suggesting that the compound does not contain any halogens (Cl 2 peaks
75:25; Br -2 peaks 50:50) and that the molecular weight of #73 is approx. 58 g/mol. Because this is an
even number, the compound contains either no Nitrogen atoms, or an even number of Nitrogen atoms.
To determine the molecular structure of #73, the IR spectrum for the compound was analyzed. The C-H
stretch on the spectra produced was to the right of 3000cm-1, which indicates the compound contains only
aliphatic (saturated) C-H bonds and does not contain ring structures, C=C, or , conjugation. A strong
absorption peak was present between 1760-1690cm-1, indicating the presence of the carbonyl (C=O) group.
The C=O peak fell at approximately 1715cm-1, suggesting the compound could be a saturated aliphatic
ketone. A single absorption in the 1100-1300cm-1 range confirms that the C=O belongs to the ketone
group.
To confirm this, all five of the other C=O groups must be eliminated. Because there was only one C-O
stretch present between 1100-1300cm-1 , it is safe to conclude -that the C=O does not belong to the ester
group. Also, no O-H band was present 3200-3500cm-1 or at 2850-2750cm-1, indicating that the C=O does

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204

not belong to the carboxylic acid group or the aldehyde group (respectively). The C=O does not belong to
the amide group because there was no N-H peaks near 3500cm-1. Lastly, the C=O does not belong to the
anhydride group because there is only a single C=O stretch band (not two) present between 1740-1775cm 1
and no C-O stretch bands were present between 900-1300cm-1
The IR spectrum shows that the ketone group is the only functional group present in the compound. The
C=O group accounts for 28amu of the 58 integral mass. The remaining mass (58-28=30) belongs to one or
more hydrocarbon groups. The basic structure for a ketone must be R-CO-R. Since the hydrocarbons
must be aliphatic (saturated), there must be 2 additional carbons (24 amu) and 6 hydrogens (24+6=
30amu) present in the compound. Therefore, the molecular formula for #73 is C3H6O. Two peaks present
in the fingerprint region at approximately 1375cm-1, indicated that there were two CH3 groups present in
the structure of the compound.
All of the data collected on #73 agrees with the literature values of the compound 2-propanone (acetone)
(see literature summary table below). One potential source of error in this experiment is the thermal
inefficiency of the distillation apparatus. Measures taken to enhance the thermal efficiency in this
experiment (i.e. insulating the joints of the apparatus thoroughly with aluminum foil) were effective in
acquiring the most accurate data possible, as the boiling point identified and the IR spectrum generated
for the unknown agreed with the literature values for the compound identified.

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204

Literature Summary (Unknowns, Synthesized Compounds)

Unknown No.
CAS No.
Name (IUPAC)

#73
67-64-1
2-propanone

Synonyms

Acetone, Dimethyl
ketone, Ketone
propane

Melting Point
(oC)

Lit -94.9oC
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Boiling Point
(oC)

Lit 56.08 oC
Exp 53-56oC

Lit
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Lit
Exp

Refractive Index Lit 1.3588

(nD20)
Exp 1.3592
Solubility
(Rel to Water)

Lit Miscible
Exp Miscible

Lit
Exp

Lit
Exp

Lit
Exp

Density
Rel to Water

Lit 0.7845 g/cm3

Exp

Lit
Exp

Lit
Exp

Lit
Exp

Molecular
Formula

Structural
Formula

C3H6O

Experiment:

Date:

Infrared Mass Spectroscopy and UV Spectroscopy

Name

Partners

Katheryn Soto

N/A

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204