Forces and Bonding: The Liquid Project

2 weeks; work in pairs.

Goals

To provide a research project involving a number of aspects of chemical identification, structure,

and reactivity
To enhance observation skills
To learn and reinforce techniques of characterization
To enhance skills of experimental design and strategy

Background
The purpose of this project is to give you an extended, research-like laboratory experience solving a
frequently-encountered problem in chemistry - characterization and identification of an unknown
material and communicating your work and results to your peers in a formal technical document.
Unlike the 1-period experiments you have performed up to this point, this project will occupy two
successive weeks and will be conducted at your pace and according to your experimental decisions.
Instructors will be on hand to provide guidance, but the responsibility for advancing the project to a
meaningful conclusion will be yours.
Before coming to lab each week, you should come prepared and organized with what you would like
to achieve. We expect that you will maintain your laboratory notebook as instructed. In addition to
this, you will be expected to submit a formal research report on your findings. Your laboratory grade
for this two-week project will be based on the quality of this report and the lab notebook.
You will work with a partner throughout the project. At the first project lab period, you and your
partner will be given a sample of a common liquid. You must then proceed to address the following
project objectives:
1. Explore the physical properties of your liquid, which include:
Density
Boiling point
Freezing point
Polarity

Molar mass
Vapor pressure

You must propose a detailed procedure for determining the density

(mass per unit volume) of your liquid. Review your procedure with
the instructor before proceeding.
Two methods:
The ability of your liquid to dissolve an ionic compound, NaCl, a
polar covalent compound, glucose (C6H12O6), and a non-polar
covalent compound, naphthalene (C10H8).
Miscibility with a polar solvent and a relatively non-polar organic
solvent.
Determined using a classical approach known as the Dumas method.

2. Propose an identity for your unknown based on comparison of the physical properties of your
liquid with published data on the properties of known compounds.
To facilitate this, you will be provided with a list of compounds from which your liquid has been
selected. Using published sources, databases and other resources from the library, you will

compile a table of these compounds with their physical properties (Liquid Properties Reference
Table). This table will be graded as part of the Project Report.
3. Confirm (or not) the proposed identity of your unknown using Infrared Spectroscopy to:
a. Determine the types of chemical bonds present in molecules of your liquid.
b. Compare your unknown liquids spectrum with that of the liquid you proposed.
To give the greatest confidence in your conclusions, you should apply the following practices:
For all measurements you should report 3 best measurements that are within 5% precision.
(mean 5%)
When you are confident you know the identity of your sample, obtain an aliquot of that
compound, test it in the same experiments and calculate the accuracy of your data for the
unknown with those of the known compound.
If you have any doubts about the results of any test, check with your classmates to see if they
have had similar problems with that test (and possibly remedies!) and, as time permits, repeat
the test until you are comfortable with the results.
Your grade for this two-week project will be based on the quality of your data (precision and
accuracy), your Project Report (including the Liquid Properties Reference Table) and your lab
notebook. To ensure you get the best possible outcome for this project, you will have ample
opportunity to prepare rough drafts of your report and reference table prior to the submission deadline
for the final report: Noon December 7.

Equipment and Materials

Assorted beakers, test tubes and Erlenmeyer flasks

Pasteur pipets/bulbs
Assorted watch glasses
Product vials (1-dram)
10-mL syringes
1-, 2-, 5-, and 10-mL graduated pipets
Syringe pipet fillers
spatulas
balances
aspirator trap
liquids
10-cm length of 0.5-mm capillary tubing
Melting point capillaries
Rock salt
Infrared spectrometers

Safety
Safety goggles must be worn at all times in the laboratory. Avoid contact of the reagents with the skin.
In the event of skin contact, flush the affected area with copious quantities of cold water.

Experimental Procedures
Record all data and observations in your notebook.

Determination of Boiling Point

1. Prepare a water bath by filling a 250-mL beaker containing a 1-inch stirring bar with deionized
water and placing it on a stirring hot plate.
2. Obtain a 13 x 100 mm test tube and add about 2 mL of your liquid, then drop in a boiling stone.

3. Tape the test tube to the inside wall of the water bath so that the entire depth of liquid in the test
tube is submerged in water.
4. Place the end of a thermometer into the test tube and clamp the top end of the thermometer using
an extension clamp. Adjust the height of the thermometer so that the tip of the probe is
approximately 1 cm above the surface of the liquid.
5. Turn on the stirring motor and adjust the speed so that the liquid is well agitated but not splashing
out of the beaker (or into your liquid)
6. Turn on the heating unit, starting at a low setting and gradually increasing as needed.
7. Record the temperature at which the following are observed as the boiling point.
7.1. A steady stream of gas bubbles emerges from the stone.
7.2. Vapor of the liquid condenses on the probe and drips into the liquid.
7.3. The temperature increase slows significantly and stabilizes.
8. Turn off the heat and allow the water bath cool to below the boiling point
9. Drop another boiling stone into the test tube, and repeat steps 6-8 until you have 3 results that are
within 2% of their mean. Add more liquid as needed prior to each reheating step.
10. Record the mean and % as the boiling point.

Determination of Freezing Point

1. Prepare an ice salt bath by mixing approximately equal volumes of crushed ice and rock salt in a
250-mL beaker.
2. Add a small volume of water to the bath and stir vigorously with a stirring rod until the
temperature of the bath is approximately -10oC or lower.
3. Add ~ 1.5 mL unknown liquid to a 13 x 100 mm test tube and submerge the test tube in the ice
bath so that the liquid in the test tube is completely below the surface of the cooling medium.
4. Immediately insert a thermometer probe into the liquid in the test tube. Agitate the ice bath
periodically to ensure that its temperature stays as low as possible.
5. Record the temperature at which you see solid forming in the test tube (Tip: at the freezing point,
the temperature should remain constant until all liquid has converted to solid).
6. Remove the test tube from the ice bath, warm the liquid until it is fully melted and repeat steps 4-5
until you have 3 results within 2% of the mean. Record the mean and % as the freezing point.
If the liquid does not freeze in the ice-salt bath, report its freezing point as < T oC, where T is the
lowest measured temperature for your ice-salt bath.

Dissolving Capacity (Solvating Ability) for NaCl, glucose (C6H12O6), naphthalene

(C10H8):
7. Weigh about 0.2 g of the test compound on a tared piece weighing paper. (Record the accurate
mass in proper significant figures)
1. Dispense 1.000 mL of your liquid into a 1-dram via using an automatic pipettor with the
appropriate pipet tip attached.
2. Transfer a small portion (<5%) of the weighed solid to the vial. Stir mixture until solid dissolves
completely.
If solid does not completely dissolve, re-weigh the solid remaining on the weighing paper and
record the solubility as < mass where mass is the difference between the initial a final
masses of solid on the paper.
3. If the solid completely dissolves, continue adding small portions and stirring until the most
recently added portion fails to completely dissolve.
4. Determine the mass of the solid remaining on the weighing paper.
If the solid stops dissolving before you have used the entire sample, report the difference
between the initial and final masses as the solubility.

5. If all of the solid from steps 1-4 dissolves, weigh another ~ 0.2 g of the sample and continue
adding in small portions until it fails to dissolve. DO NOT ADD MORE THAN 0.8 g.
a. If the entire 0.8 g of sample dissolves in your liquid, report the solubility as > 0.8 g/mL.
6. Calculate the solubility of the solid in your liquid (g/mL).
7. Repeat steps 1-7 until you have 3 measurements within 5% of their mean

Determination of Molar Mass by Dumas Method

8. Prepare a hot water bath as described in Determination of Boiling Point. Insert a thermometer into
the water and heat the water to a temperature above the boiling point of your liquid.
9. Thoroughly clean and dry a 50-mL vial with septum cap, both inside and out and obtain a 21 g or
smaller needle.
10. Determine the mass of the vial with the septum cap 0.0001 g using an analytical balance.
11. Using a pasteur pipet, add 20 drops of your liquid into the vial. Fit the septum cap tightly on the
mouth of the vial and insert the needle into the septum cap.
12. Clamp the vial in a hot water bath so that most of the vial is submerged.
13. When all of the liquid in the vial has vaporized, remove the vial from the bath and record the
temperature of the bath. At this point, the vial contains ONLY the vapor phase of your liquid.
14. Thoroughly dry the outside of the vial using a Kimwipe, and allow the vial and contents to return
to room temperature. As the vial cools, you may observe some condensation inside.
15. Once the vial has returned to room temperature, remove the needle from the assembly and reweigh the vial.
16. Repeat the steps 1-8 twice more. Use the average difference between the initial and final masses to
calculate molar mass.
17. After the last repeat of step 9, clean the vial and fill it with deionized water, find the mass of the
water in the vial. Using the density table for water, find the volume of water at the room
temperature you are operating the experiment. The volume of water in the vial gives a measure of
the volume of the vial.
18. Record the atmospheric pressure in the laboratory.
19. Use the bath temperature, mass of vapor, volume of vapor and atmospheric pressure to calculate
the molar mass of your sample. (Hint: Remember the gases lab.)

Vapor Pressure by a Syringe Method.

20. Obtain a small side-arm test tube, a 10-mL glass syringe, a septum cap to fit the mouth of the test
tube, and a 1-mL plastic syringe.
21. Thoroughly clean the test tube with deionized water, rinse with acetone and allow to dry
completely.
22. Ensure the syringe is clean and dry by rinsing the inside wall of the barrel and the surface of the
plunger thoroughly with acetone. Wipe the entire surface of the plunger and dry the inner wall of
the barrel with a Kimwipe. Insert the plunger and move it in and out several times. Withdraw it
and let acetone evaporate from its surface. Repeat the insertion and withdrawal until the acetone is
gone. At this point, the plunger should slide and rotate freely, with almost no friction.
23. Do not proceed until you are satisfied with the results of steps 2 and 3.
24. Remove the plunger from the 10-mL glass syringe and lay it on a clean Kimwipe on the bench
while you set up the apparatus in Figure l. Attach a short length of appropriately sized rubber
tubing to the end of the glass syringe. The fit must be tight. Attach the other end of the tubing to
the sidearm of the test tube. This fit must also be tight. Use ring stands and clamps to mount the
test tube vertically and the syringe horizontally. BE SURE THAT THE SYRINGE IS EXACTLY
HORIZONTAL SO THAT WHEN THE PLUNGER IS REPLACED, IT WILL NOT FALL OUT
AND BREAK. DO NOT TIGHTEN THE CLAMP ON THE SYRINGE BARREL--INSTEAD,
ALLOW THE SYRINGE TO REST ON THE LOWER ARM OF THE CLAMP. Then replace the
plunger in the barrel of the syringe.

25. Fit the solid end of the septum cap tightly into the top of the test tube and fold the hollow end over
the lip of the tube.
26. Insertion of the septum cap will probably affect the position of the syringe plunger. Write down
the plunger position.

27. Draw 0.1 mL of your liquid into the 1-mL plastic syringe.
28. Insert the syringe needle completely through the septum on the sidearm test tube (you should see it
protruding from the underside of the septum).
29. Rapidly inject all of the liquid into the test tube and immediately withdraw the syringe.
30. Observe the position of the plunger of the glass syringe. (Tip: Gently tap the syringe to overcome
any stickiness of the plunger.) Record the final plunger position and calculate the difference
between the initial and final volumes.
31. Remove the septum cap from the test tube, and aspirate the test tube to remove ALL TRACES of
your liquid, both liquid and vapor. While aspirating, move the plunger of the 10-mL syringein and
out at least 10 times to expel all vapor of your liquid.
32. Repeat steps 6-12 until you have 3 measurements within 5% of their mean.
33. After completing step 14, Measure the volume capacity of the side arm test tube by inserting the
septum cap, and filling the tube through the sidearm with distilled water. When the tube is
completely full, pour the contents into a graduated cylinder. The volume of water in the cylinder is
a good estimate of the volume capacity of the sidearm test-tube portion of the vapor pressure
assembly (ignoring the small contribution from the syringe).
8. Use your data to calculate the vapor pressure of your liquid in torr, using the following equation,
where Patm is local atmospheric pressure, V is the average volume increase following liquid
injection, as measured in the glass syringe, and Vf is the total final volume of the system (volume
capacity of side-arm test tube plus final reading of glass syringe plunger position).

Pvap = PatmV/Vf
9. Thoroughly clean and dry the sidearm test tube and syringe .as described in steps 2 and 3.

Infrared Spectroscopy of a liquid:

Liquid Sample Preparation
1. The IR cell should never be placed directly on a lab bench. Lab benches are DIRTY. As is
always recommended, place 3 2-foot strips of clean paper towel on your bench space and
place the cell either on that or on a large Kimwipe.
2. The salt crystals (transparent discs) between which the sample is placed must NEVER be
exposed to water. They will be dissolved, hence destroyed by, water.
3. The salt crystals must NEVER be handled directly with the fingers. Please wear CLEAN
surgical gloves when handling the crystals, or handle them with a Kimwipe. The crystals must
be handled by the EDGES only--never touch the polished faces of the discs.
4. Your IR cell may involve threaded parts. UNDER NO CIRCUMSTANCES ARE YOU TO
CROSS-THREAD THESE PARTS. THIS WILL RUIN THE THREADS. If the threads are
not properly aligned, the parts will not turn together smoothly. DO NOT FORCE THE TURN.
Back off, realign the parts correctly, and gently turn the male piece to tighten.
5. Do not use excessive pressure when assembling the IR cell. This will fracture the salt crystals.
6. To load the IR cell with a liquid sample, follow these steps:
a. Wear CLEAN gloves.
b. Remove the IR cell from the storage desiccator.
c. Carefully disassemble the crystal holder by unscrewing the plastic (male) piece, as
shown by the instructor. Place the pieces on a clean paper towel strip or Kimwipe
(NOT ON THE BENCH).
d. CAREFULLY remove the crystals by inverting the metal part of the crystal holder.
Catch the crystals in a clean Kimwipe. Remember, the crystals are table salt! DO
NOT EXPOSE THEM TO WATER OR BARE FINGERS.
e. Using a CLEAN Pasteur pipet, place 1 drop of the liquid to be studied in the center of
one of the the crystals.
f. Place the other crystal squarely on top of the first crystal, so that the liquid spreads
into a film.
g. Place the salt crystals with the liquid into the metal holder.
h. Reassemble the cell by screwing in the plastic holder piece. BEWARE OF CROSS
THREADING and DO NOT OVER TIGHTEN!
i. Place the Pasteur pipet upside down in the broken glass container.
Collecting the IR Spectrum and cleaning the cell
34. Place the cell on the cell mount of the IR spectrometer.
10. Obtain the IR spectrum of the sample. Your Lab Instructor will assist you with this. Be sure to do
the following
b. Record the pertinent spectrophotometer settings (range, scan speed, repeat scan)
c. While the spectrum is on the computer screen, insert a label with the unknown liquid number,
both partners names and the date.
d. Print the spectrum and email a copy to yourself from the computer. (Important: All spectra
will be deleted at the end of the day!)
11. Remove the cell from the mount of the instrument.
12. Disassemble the crystal holder.
13. Remove the crystals.
14. Clean the wet crystal surfaces by BLOTTING (NOT rubbing) the liquid from the faces of the
crystals using a Kimwipe and rinsing the crystals with NaCl-saturated acetone. Allow the crystals
to air dry and return to the dessicator.

Additional Procedures (If Time Permits)

Miscibility with water and dichloromethane
1. Carefully add your liquid to a 10 mL graduated cylinder until the liquid meniscus is at exactly the
5.00 mL mark.
2. Measure and record its temperature, and withdraw the thermometer. Check to make sure that the
volume level in the cylinder does not change significantly when the thermometer is withdrawn.
3. Using a 5 mL graduated pipet, draw up 5.00 mL of deionized water and eject the liquid from the
pipet to the graduated cylinder containing your liquid. This must be done forcefully enough to
result in mixing of the liquids, but not so forcefully that splashing occurs.
4. Immediately after mixing, record the total volume of the mixture, then stir the mixture with the
thermometer and record the temperature of the mixture.
5. Record any other observations that you consider pertinent.
6. Clean and dry the graduated cylinder with water and acetone.
7. Repeat steps 1-6 using dichloromethane instead of water.
8. Give the graduated cylinder a final cleaning with water and acetone.

Determination of Freezing Point Below -15C

1. Only do this procedure if your liquid did not freeze at the lowest temperature achievable in the icesalt-water bath.
2. Add ~ 1.5 mL unknown liquid to a 13 x 100 mm test tube.
3. Insert the test tube into the rack in the refrigerated cooling bath located at the back of the lab such
that the liquid in the test tube is completely below the surface of the cooling medium.
4. Immediately insert a thermometer probe into the liquid in the test tube. You do not need to agitate
the tube due to the circulation of the bath liquid.
5. Record the temperature at which you see solid forming in the test tube (Tip: at the freezing point,
the temperature should remain constant until all liquid has converted to solid).
6. Remove the test tube from the ice bath, allow to warm until the liquid is fully melted.
7. Repeat steps 3-6 until you have 3 results within 2% of the mean. Record the mean and % as the
freezing point.

Clean-up

Clean glassware by recommended procedures, shake off excess water.

Clean graduated pipets, and vials by recommended procedures, shake off excess water, and
return to your hood.
Return all borrowed equipment to the TA / instructor before leaving lab.
Clean up your work area before leaving lab.

Waste Disposal
Dispose of all solids, liquids, and solutions in the appropriately marked waste bottles.
Discard used pipet tips in regular trash.