CHEM 2400L
PRELAB ASSIGNMENTS AND
LABORATORY HANDOUTS
CHEMISTRY 2400L
ORGANIC CHEMISTRY LABORATORY I
Spring 2023
 

Handouts to accompany:
th
A Microscale Approach to Organic Laboratory Techniques, 6 ed.
Pavia/Lampman/Kriz/Engel
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COVID Related information

Refer to the following link for additional information: [Link]
 Students must wear appropriate face coverings while indoors and those without will be
asked to return upon obtaining one. Limited exceptions can be obtained by contacting
the Office of Services for Students with Disabilities.
 Students unwilling to wear a mask will be asked to leave immediately and appropriate
security protocol (including class cancellation) may occur at the discretion of the
faculty, who may then assign additional work due to non-compliance.
 Students who are positive or are exhibiting COVID-like symptoms, must leave the
space immediately and faculty will follow up regarding make-up work and
accommodations at a later time.
 For additional details please check the Return of the Pack website.

Lab Delivery
For now, instruction will be face-to-face. In the event that face-to-face instruction is no longer
possible (due to campus closure), then all lectures and assignments will be delivered via
Zoom and Canvas. All Exams and Quizzes will be in person unless there is a valid medical
excuse or approval by Services for Students with Disabilities.

Accommodations for Students with Disabilities

• If you are in need of an accommodation for a disability in order to participate in this class,
please let me know ASAP and also contact Services to Students with Disabilities at UH-183,
(909)-537-5238.
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Lab Schedule: see laboratory handouts for pre-laboratory (pre-lab) assignments, lab sheets,
and augmented experiments. Please note that this may be subject to change depending
on COVID.

Dates Experiment What’s Due

Week 1: No Lab Nothing

Jan. 23, 25

Week 2: Safety introduction, Lab check-in, Nothing

Jan. 30, Feb. 1

Week 3: Experiment: “Introduction to Prelab Procedure for week 3

Feb. 6, 8 microscale” option A Safety Handout from week 2
Experiment: “Solubility” options
A-D
Week 4: Experiment:”Extraction”, options Prelab Procedure for week 4
Feb. 13,15 A, B, and D Solubility lab report

Week 5: No Lab
Feb. 20, 22

Week 6: Experiment: “Extraction”, option Prelab Procedure for week 6

Feb. 27, March 1 D optional

Week 7: Conformational Analysis Extraction lab report

March 6, 8 (computer lab exercise) Bring
models
Week 8: Experiment: “Spearmint and Prelab Procedure for week 6
March 13, 15 Caraway Oil: (+) and (-) Extraction and Conformational
Carvones, options A and B” Analysis lab reports
Lab Exam
Week 9: Experiment: “Simple and Prelab Procedure for Week 7
March 20, 22 Fractional Distillation”, option A Carvones lab report
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Week 10: Spring Break
March 27, 29

Week 11: PowerPoint lecture on Infrared and Simple/Fractional Distillation lab

April 3, 5 Ultraviolet-Visible Spectroscopy: report
run IR spectrum
Week 12: PowerPoint lecture on Nuclear IR assignment
April 10, 12 Magnetic Resonance
Spectroscopy Part 1;
Week 13: PowerPoint lecture on Nuclear
April 17, 19 Magnetic Resonance
Spectroscopy Part 2; run NMR
spectrum
Week 14: Experiment: “Crystallization”, Prelab Procedure for Week 11
April 24, 26 options A, A optional, and D

Week 15: Experiment: “Reactivities of Some Prelab Procedure Week 12

May 1, 3 Alkyl Halides” Spectroscopy Problem Set
Crystallization lab report

Week 16: Lab check out, Lab Final Reactivities of Alkyl halides lab
May 8, 10 report

Important Notes:

a. Prelab procedures (available on Canvas) are due most weeks. These are due 24 hours
before lab (prelab procedures), and prior to your lab meeting (prelab quizzes).

b. You must obtain instructor's signature on each worksheet before leaving lab.

c. When IR or GC data is obtained, one partner should turn in the printout, and the other a
photocopy. All peaks should be labeled, and there should be a title, and structure(s) as
appropriate on the scan or keyed to it.d. Labs are due in the first ten minutes of the indicated
period. Ten percent will be deducted for each weekday late (i.e. if your lab section meets
Tuesday noon, then at 12:10 thru Wed would be 10% off; Thursday 20% off, etc.)
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Name: Lab day/time
Week 2: Safety introduction, Lab check-in, and computer lab orientation
Chemistry 2400L, Spring 2023
PRELAB: Read the following sections in the Pavia et al. laboratory text: Technique:
“Laboratory Safety”, Technique: “Laboratory Glassware: Care and Cleaning”,
Technique: “How to Find Data for Compounds.” No prelab procedure for this week
only!
*The Techniques are in the back of your lab manual. There is also a list of
techniques towards the end of the table of contents in your text.
Safety Scavenger Hunt and quiz
i. Find each piece of equipment in the lab room or building, and indicate its location:
a. Eyewash
b. Safety shower
c. First aid kit
d. Material Safety Data Sheets (MSDSs)
e. Hot gloves
f. Mercury spill kit
g. Fire extinguisher
h. Nearest exit(s) from room
i. Three staircases in building
j. Waste container
k. Safety goggles
l. Chemicals for 2400L
m. Fire alarm
Questions:
i. When is it appropriate to wear your safety goggles in lab? What are the consequences
for failing to do so?
 
 
ii. What are the three main points of entry for chemicals into your body, and how can you
minimize each?

iii. What are the two potential consequences of pouring chemicals back into the reagent
bottle?
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iv. What does NFPA stand for and what does each color diamond represent?

v. What does a "3" in the red box indicate of the NFPA symbol mean? A "2" in the blue
box?
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Name____________________________ Lab day/time________________________

Week 3: Introduction to microscale (option A) and Solubility (options A-D)

Chemistry 2400L, Spring 2023
Prelab: Read the following in your lab text: The introductions to both the “Introduction to
microscale” and “Solubility” experiments. Also read “Introduction to microscale,
option B” and “Solubility, parts A-D”.
Read about the following techniques in your lab text: “Measurement of Volume and
Weight” and “Solubility.”
Complete the online prelab (on Canvas) before lab, submit your procedure online
through Turnitin at least 24 hours before class. Be sure to print out your procedure.
PROCEDURE
Safety: Methylene chloride (CH2Cl2, or dichloromethane) is a suspected carcinogen. Avoid
leaving open flasks and breathing its fumes. Dispose of methylene chloride in the organic
waste bottle. Diethyl ether, hexanes, and organic alcohols are highly flammable, and all
sources of heat, sparks, and flames should be avoided when it is in use. You should avoid
breathing the vapors. 6.0 M HCl and 6.0 M NaOH are caustic, and contact with skin and
clothes should be avoided. If contact does occur, flush the skin or fabric with copious
amounts of water. All non-chlorinated organic materials should be disposed of in the regular
organic waste bucket. Aqueous layers should be combined, neutralized (use a drop of
phenolthalein and add acid or base as needed until an endpoint is reached), and poured
down the sink.
Laboratory Exercise 1, Option B: Using a Dispensing pump. Note that we will be dispensing
1.0 ml of water and hexane, not 0.5 ml.
Safety/Waste disposal: Dispose of extra hexane in the non-halogenated organic waste
container found in the main hood. All tap water free of hexane can go down the sink. Any
tap water contaminated with hexane should also be placed in the non-halogenated organic
waste container.
Mass of Empty vial: Mass of vial with H2O:
Mass of H2O dispensed:
Volume of H2O dispensed: (check the volume on the dispensing pump)
Calculated density of H2O (= mass/vol.): g/mL (lit = 0.997)

Show calculations:

Mass of Empty vial: Mass of vial with hexane:

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Mass of hexane dispensed:
Volume of hexane dispensed: (check the volume on the dispensing pump)
Calculated density of hexane (= mass/vol.): g/mL (lit = 0.660)
Show calculations:

Experiment 2: Solubility,
Follow the procedure in the text for parts A-D, Experiment 2. Fill in the charts below as you
go. Be sure to mix completely and consistently before noting solubilities.
Part A. Solubility of Solid Compounds
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Part B. Solubility of Different Alcohols

Solvents

Alcohols Water Hexane

Methyl Alcohol
CH3OH

1-Butanol
CH3CH2CH2CH2OH

1-Octanol
CH3(CH2)6CH2OH

Part C: Miscible or immicible pairs?

Water and ethyl alcohol Water and diethyl ether
Water and methylene chloride Water and hexane
Hexane and methylene chloride

Part D. Solubility of Organic Acids and Bases

Additional Questions
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1. Compare your calculated densities (part 1) to literature densities. What source(s) of error
contributed to differences in these values?

2. Water and hexane don't mix; that is, they form two layers when placed in the same
container. Which compound would comprise the top layer? Explain.

3. Why is it necessary to keep the pipettes separate; that is to use the H 2O pipette only for
H2O, and hexane pipette for hexane only?

4. Explain the observed solubilities for part 2A for all three compounds. Consider polarity of
the solvent and solute, and the possibility of hydrogen bonding.

5. How does the solubility of alcohols in water and hexane vary, with number of carbon
atoms in the alcohol molecule? (Hint: look at the ratio of carbon atoms to hydroxyl groups
in the alcohols tested, and consider how this ratio affects solubility in water and hexane).

6. What would you predict for the solubility of 1,5-hexanediol in water? In hexane? Explain,
considering your answer to question 5, above.
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7. Extraction is a technique in which two immicible solvents are used to separate

compounds, based on solubility. Based on experiment 2C, give two examples of immicible
solvent pairs that might be used for extraction.

8. Write out and discuss the acid/base reactions that occur in part D in order to explain your
solubility observations. Be sure to discuss the charge and polarity of each species, and
how these affect water solubility. (hint: what happened when 1.0 M HCl was added to
ethyl 4-amino benzoate, then 6.0 M NaOH, as well as 1.0 M NaOH to benzoic acid, then
6.0 M HCl)?
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Prelab Week 4 worksheet (hold on to until week 4). Complete and bring to lab with you. This
is part of your prelab grade.

Procedure for Experiment: “Extraction, Part D Optional”: Separation of a neutral compound

from a mixture containing a basic impurity.
Measure out ____ g of an unknown mixture containing a compound and a neutral
compound.
1. Add this solid and mL of to a screw top centrifuge tube.
Mix completely.
2. Add mL of to the tube and mix thoroughly. Removed the
layer with a pipette to a labeled test tube.
3. Repeat step 3.
4. Add M to the removed layers in the test tube dropwise until a ppt.
forms. The identity of the ppt. is .
5. To the remaining in the centrifuge tube, add mL of
and mix thoroughly. Remove the layer to a labeled “holding” test
tube for later disposal.
6. Transfer the layer, remaining in the centrifuge tube, to a clean, dry test tube.
Add to remove the remaining water, wait minutes.
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7. Remove the liquid, containing dissolved to a
clean, tared container. Evaporate the solvent in the hood (don’t overheat). Determine
the mass and melting point of the solid remaining.
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Name____________________________ Lab day/time________________________
Weeks 4&6: Extraction (options A, B, D, and D optional)
Chemistry 2400L, Spring 2023

PRELAB: Read about the following Experiment: “Extraction” (parts A, B and D).
Read about the following techniques: “Extraction, Separations and Drying Agents”,
“Physical Constants of Solids: The Melting Point”, and “Filtration” (section on vacuum
filtration only).
Complete the reading. Write a complete procedure for parts A, B, and D (not D-optional)
and submit to Turnitin 24 hours before lab; bring a copy of the procedure to lab with you.
ALSO complete the prelab calculation for Part A before lab.
FOR WEEK 4 Week 4 Prelab: Complete the proceeding prelab sheet (p. 11 of this
handout). This must be done prior to lab. Bring your completed sheet to week 4 lab at the
beginning of the period, prepared to show it to your instructor, and use if for performing part
D, optional. There is no Turnitin procedure due for week 4.
PROCEDURE
Safety: If you need to heat your sample to dissolve all of your caffeine, allow this
solution to cool to room temperature before adding methylene chloride. Methylene
chloride (CH2Cl2, or dichloromethane) is a suspected carcinogen. Avoid storing or
transporting in uncapped flasks, and avoid breathing its fumes. Evaporate excess methylene
chloride on a water or sand bath in the fume hood. Dispose of methylene chloride in the
halogenated organic waste bottle. Diethyl ether is highly flammable, and all sources of heat,
sparks, and flames should be avoided when it is in use, as should breathing the vapors. All
other organic materials should be disposed of in the regular organic waste bucket; aqueous
layers should be combined, neutralized (use a drop of phenolthalein and add acid or base, as
needed, until an endpoint is reached), and poured down the sink.
Follow the procedure in the text for parts A, B (you will be assigned one of the three
compounds shown), D and D-optional During weeks 3 & 4. Put your data for part B on the
board during week 4, and be sure to obtain class average data on week 4. You should write
up a procedure for part D-optional on the provided worksheet (p. 12) prior to Week 4, and
show the instructor before proceeding. Turn in this page stapled to your report on Week 5.
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Part A. Extraction of Caffeine
Amount of caffeine added:
Calculated theoretical recovery, total mass: show calculations

Amount of caffeine recovered (in g):

Percent caffeine recovered (in g): show calculations

Part B. Distribution Coefficient add your data to the table posted!!

Identity compound used:

Amount used (g):

Amount solid recovered from CH2Cl2 layer (g):

Distribution Coefficient for this solute between dichloromethane and water:

(show calculations)

Part D % D-optional. Data

Neutral component D MP range*_________ mg recovered _______ % recovery
______
Acidic impurity—is there precipitate visible in the first NaOH tube? ____ The second? ____
Neutral component D-optional MP range*_________ mg recovered _______ % recovery
______
Basic impurity-- is there precipitate visible in the first HCl tube? ____ The second? ____
*MP Range contains two values, spanning the temperature range from the point at which the
first drop of liquid appears, to the point at which the last solid is converted to liquid
Instructor initials obtained after showing sample recovered (D)
(D-opt)
Show calculations for % recovery: (based on amount of unknown mixture used; you can
assume that 0.100 g of neutral component was mixed with 0.050 g of either the acidic or
basic impurity)
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Identity of Neutral component D, and lit MP:

Identity of Neutral component D-optional, and lit MP:

Procedure for determining melting points (keep this page for reference):
Your goal is to determine an accurate melting range for your compound. This accomplished
in two steps, using two samples
1. Determine approximate melting point using the first sample by heating quickly to up to 200
o
C
2. Determine an accurate melting range using the second sample while slowly heating
through the melting range.
Step 1: approximate melting point.
a. Prepare two identical melting point samples as indicated in the lab book (1-2 mm,
packed firmly), (see Technique: “Physical Properties: The Melting Point”
(section called Packing the Melting Point Tube).
b. Insert one sample tube into the MP apparatus and turn on the power. Make sure
you can see the whole sample, and that the temperature of the apparatus (seen on
the thermometer) is well below the expected melting point of the unknown to avoid
premature melting.
c. Set the heating dial to about 7 to heat quickly.
d. Observe the sample carefully and note the temperature at which the sample starts
to melt. Quickly stop heating by turning the knob back to zero.
Step 2: melting range
1. Allow the apparatus to cool to 15 oC below the approximate melting temperature.
2. Insert the second melting-point tube, and check to make sure the sample is visible and
that it has not begun to melt. Start heating to the set point by turning the knob to a lower
number (2-3) and carefully watch your sample to see if it has begun to melt. If after 2
min. the temperature has not risen, turn the knob, one number at a time higher until the
temperature begins to rise slowly.
3. The temperature should continue to rise at no more than a few degrees per minute while
you observe your sample. When the first drop of liquid appears in the melting point
capillary, record this as the initial temperature. Continue to watch your sample until it
has completely liquefied. Record this as the final temperature. These two temperatures
are the melting point range, often called improperly the "melting point."
1. Return the heating knob to zero, turn off the electronic thermometer, and remove
your used melting point capillary. The melting point capillary should be placed into one
of the glass waste containers on the bench near the melting point apparatus. You must
 16
wait until the temperature is below the desired set-point before you can begin
examining a new sample.

Safety/Waste Disposal: Dispose of the melting point tube and unused sample in the
indicated waste containers. And remember: the MP apparatuses get hot.

Questions
1. Each of the solvents listed below are used in experiments in this course. Will the
organic phase be in the upper or lower layer when each of the solvents is mixed with
water? Methylene chloride; pentane; toluene; diethyl ether.

2. Examine the class distribution coefficients calculated in part b. Draw structures for the
three solids below, and label each with the average of the class distribution
coefficients. Explain whether the average distribution coefficients are what are
expected for the relative solubility of the solids in water vs. dichloromethane.

3. Suggest a qualitative test (based on solubility) that would differentiate a pure acidic
organic compound from a neutral organic compound. Indicate clearly how the test
would be done: steps to be taken, what result would be expected for an acidic
compound vs. a neutral compounds. Hint: lab 2 contained a series of qualitative tests.
Qualitative solubility tests give different (visible) results for different types of
compounds. Complete on a separate page, please.
DON’T FORGET TO TURN IN COPIES OF pg 11 AND PRELAB CALC WITH THIS
LAB
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Name: Lab day:
Week 7: Conformational Analysis
Chemistry 2400L, Spring 2023
No Prelab procedure this week.
BRING YOUR PLASTIC MODELS TO LAB WITH YOU, OR BORROW A SET.
Part 1. Butane
1. Make a plastic model of butane.
2. Look perpendicular to ("down") the 2,3-bond of your (plastic) butane molecule. Begin with
the two methyl groups eclipsing one another (0° dihedral angle). Next, rotate your model
around the 2,3 bond in 60° increments. Locate each unique conformation, staggered or
eclipsed, gauche and anti.
3. Log in to a workstation in CS-333. You will work with your partner. Bring your plastic
models and this handout. Open the application “Spartan ES”. Click on the “maximize” button
on the upper right, so that the Spartan window fits properly on your screen. Spartan ES
To build a model of butane:
1. • Choose “File/new”
2. • Choose the sp3 hybridized carbon atom from the pallet
3. • Click anywhere on the drawing screen to draw the first carbon atom
4. • Click on one of the ends of the bonds to carbon to attach the second carbon atom
5. • Repeat twice to make butane
6. • Choose File/“Save as” to save molecule with an appropriate name
To Minimize this molecular model
7. •Choose “Setup/calculation”
8. • Choose “Equilibrium Geometry”, then “Molecular Mechanics” and “MMFF” on the
setup box, then OK

9. • Click on the “minimize energy” icon.E

The energy of this conformation will
be displayed in the lower right hand corner of the screen. The energy should be in
units of "KJ/mol” or in “kcal/mol.” If you are getting units of “au,” notify your instructor.
10. Examine the resulting model
11. • Choose different views from the Model menu
12. • Rotate, translate, and zoom the model using the right/left mouse keys with or without
the control key (try this)
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13. • Measure the bond lengths, bond angles, and dihedral angle (for example, to
measure dihedral, choose Geometry/“Measure dihedral” then click on the four carbon
atoms in a row).
14. Record: the minimized dihedral angle:

Now you are ready to create the four conformers extreme conformers for butane (discussed
in Chapter 4 of Smith textbook from lecture). You must “constrain the dihedral” angle of the
model, at each of the indicated values (0, 60, 120, 180 deg), then minimize each model, by
following the steps below:
1. • Remove the previous dihedral angle constraints by choosing Geometry/”Constrain
dihedral.” Click on the four carbons in a row, then click on the purple padlock (bottom
right corner) to unlock this constraint.
2. Choose Geometry/”measure dihedral” Now click on the four carbons of butane in a
row from one end of the molecule to the other.
3. • Enter the desired dihedral in the box in the lower right corner of the screen, then
“Enter”. The model will convert to the desired dihedral angle. Rotate the molecule on
the screen with your mouse, to view it from different angles.
4. • Choose Geometry/“Constrain dihedral
5. • Click on the purple lock next to the box in the lower right of screen (Your model
should now show a purple line and lock picture across the central C-C bond.)
6. • Click on the minimize energy icon. Measure the energy, bond lengths, bond angles,
and dihedral angle as before.
7. Repeat for the remaining dihedral angles.
Record the energies of each conformer, and measure dihedrals, and distances between end
carbon atoms (with “measure distance”). Leave the final two columns blank for now.
 19

RECORD DATA for each conformer in this table:

Dihedral angle Distance C1-C4 Energy Relative energy Relative energy

calculated calculated from text (see
(kcal/mol) or chapter 4 of
(KJ/mol) Smith text)

60

120

180

IMPORTANT NOTES:
Calculate the relative energy (calculated) by taking the lowest energy and subtracting it from
the other energies. If you do this calculation correctly, one of the conformers should have a
“relative energy (calculated) of zero, and all others should have positive energies. Now, plot
the relative energies (calculated) on the y-axis vs. dihedral angle (x-axis) for the four
conformers. Plot a second line in a different color or pattern, showing the energy values from
the text.

On the graph above, Label each minima and maximum on your graph (minima are "valleys",
maxima are "hills"). Then Label each minimum or maximum as either eclipsed or staggered
and include syn, gauche, anti etc at needed.
Questions:
1. Are the maximum/minimum values the same as the text? Why or why not?
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2. Why are the different minima not the same energies?
Close all files on the screen.
Part B: Cyclohexane chair and boat:
1. With your plastic models, attach 6 sp3 carbons in a ring. Arrange the ring into a puckered
“chair”. Show to your instructor if you are unsure if you have a chair. One clue: three of
the “H’s” should be “up”, the ring horizontal, three H’s should be “down”. These six up-
down positions are called axial.
2. On the computer: To prepare the cyclohexane chair, clear the screen (File/New), then
click on “rings” on the building pallet and choose the cyclohexane ring, then click on the
main desktop. Setup and submit this calculation, as above.
Data for chair
a. Record the energy of the molecule (kcal/mol)
b. C-C-C angles
c. C-C-C-C dihedral angles
d. H-H distances on adjacent carbons (closest H’s)
e. Are there any gauche interactions?
f. Sketch the model and identify the axial and equatorial H’s.

3. Convert your plastic model chair to a boat, by bringing the “foot” of the chair up. Check
with your instructor to make sure it is a boat.
4. Look down each bond in the boat cyclohexane. Record all eclipsing interactions you
see.

5. Are there any significant steric repulsions in your boat model?

6. On the computer: Download the “cyclohexane twist boat” file from the course Canvas
site, then open this file in Spartan. DO NOT minimize this structure. Compare this structure
with the boat you built with your plastic models. See if you can convert the boat you built with
plastic models into a twist boat. Hint: it is a small movement.

7. Data for Twist Boat (on the SpartanES screen).

a. Record the energy of the molecule (kcal/mol)

b. C-C-C angles (are they all the same?)

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c. C-C-C-C dihedral angles (are they all the same?)

d. H-H distances on adjacent carbons (closest H’s)

e. How is this twist boat minimum structure different than a boat?

f. Why did the computer minimized to a twist-boat, and not a boat?

Sketch the twist-boat below.

Close all files on the screen.

Part C. Substituted Cyclohexanes.
After completing part B, this should be easy. Clear the screen (file/new) and use the
cyclohexane template to start. Add the diaxial, diequatorial, or equatorial/axial 1,3-dimethyl
groups one set at a time, minimize each structure, and record the data below.
Data for disubstituted cyclohexanes

Two methyl Distance between Cis or trans? Energy Relative energy

groups methyl carbons (kcal/mol)

1,3-diaxial

1,3-diequatorial

1,3-equatorial/
axial

Complete this sentence based on your data in the table above:

The _ (more/fewer) _ axial methyl groups, the (greater/lesser) the energy of the molecule.

Sketch and label all three models in three dimensions below.

 22

Close all files on the screen

16D. Cis and Trans-2-butene
File/New. To build 2-butene, choose the “sp2 carbon” atom. Click on the screen to draw the
first alkenyl carbon. Then click on the double bonded end of this to add the second alkenyl
carbon. Now, choose the “sp3/carbon” atom, and add a carbon to each end of the pi bond, in
either cis or trans orientation as needed. 1-butene is prepared similarly, with the alkene on
the end. Minimize each alkene structure, using the PM3 semi-empirical method (Setup
calculation, DFT-BK3LYP 6-31G*; then Setup/submit), and record the data requested below.

Butene isomer Distance Calculated Relative Relative

between methyl energy energy energy from
carbons (kcal/mol) text

Cis-2-butene

Trans-2-butene

Suggest reasons why the two isomers have different relative energies (think about what
factors affect alkene stability).
 23
Name: Lab day:
Week 8: Spearmint and Caraway Oil: (+)- and (-)-Carvones
Chemistry 2400L, Spring 2023
PRELAB: Read the following before completing your report sheet to help you answer
questions and interpret data. Read the Essay on the Stereochemical Theory of Odor
(preceding Experiment 16) also read Experiment 16. Also read Technique 22 (Gas
Chromatography); Technique 23 (Polarimetry), Technique 25 (IR Spectroscopy). Complete
the prelab procedure using Turnitin (at least 24 h before lab), and print out your
procedure.
PROCEDURE:
These samples are expensive. Use as little as possible, and do not
contaminate with a dirty pipette or by pouring back sample.
Follow the procedure in the text. All students will perform the odor test for all samples. Each
partner will run the IR, GC, and polarimetry for one of the two indicated samples, and make
copies for their partners (who will analyze the complimentary sample). Omit boiling point
determination. Also note that supervision will be required while using both the
Polarimeter and the GC/FID.
LABORATORY REPORT: DATA
ODORS:
1. Compare the odors of both Spearmint and Caraway Oils. In your own words, describe
these odors. Try to make your descriptions depict the characteristic differences and
similarities.
Spearmint oil:

Caraway oil:

2. Now describe the odors of the pure (+) and (-) carvones. Which carvone corresponds to which
oil? How are the odors of the pure carvones different from the odors of the oils?
 24
GC DATA
Obtain a GC scan for samples of both Spearmint and Caraway oils (not pure). Using the
scans in Lab textbook, assign identities to as many peaks as possible. Attach copies of both
to your lab report
Retention time for major peak of spearmint oil:
Retention time for major peak of caraway oil:
Other likely component(s) of Other likely component(s) of
Spearmint oil: Caraway oil:
Indicate the similarities and differences between retention times and components in the two
samples. Be sure to discuss each peak, and what compound it corresponds to.

IR SPECTROSCOPY:
Obtain IR spectra for both samples of pure (+)- and (-)-carvone. Include these spectra
(clearly labeled as (+)- and (-)-carvone) with your report. Label each non-fingerprint peak with
the corresponding bond stretch. (see Table IR. 25.1, in Pavia). Be sure to specify which
stretch corresponds to which bond in carvone.
-- List the major stretching frequencies in each spectrum in the table below.
-- Are there any significant differences between these two spectra (ignoring intensity)?

(+) Carvone: (-) Carvone:

Wavenumber at center of stretch (cm-1) Wavenumber at center of stretch (cm-1)
 25

POLARIMETRY
Obtain the observed rotation for the individual samples of both pure (+)- and (-)-carvone.
Show calculations
(+)-Carvone:
grams of (+) carvone: g diluted to 25 ml
Solution Concentration: ______________(g/ml) Cell Path Length:
_______________(dm)
Observed rotation [a]: _______________ Calculated Specific rotation [α]D20
_______________
Show calculation of specific rotation:

[α]D20= [α]/(conc., g/ml * length, dm)

(-)-Carvone:
grams of (+) carvone: g diluted to 25 ml
Solution Concentration: _______________ Cell Path Length: _______________
Observed rotation [α]: _______________ Calculated Specific rotation [α]D20
_______________
Show calculation of specific rotation:

[α]D20= [α]/(conc., g/ml * length, dm)

Compare these two specific rotations [α]’s to one another. Be certain to comment on any
similarities and differences. What expectation do you have for the absolute values of these
rotations? What could account for unexpected differences?
 26

ADDITIONAL QUESTIONS
1. Using the Cahn-Ingold-Prelog rules, assign priorities to the groups around the chirality
center in carvone. Draw the structural formulas for (+) and (-)-carvone with the groups
oriented in their correct positions to show the R and S configurations.

2. Which measurements were made for pure (+) and (-)-carvone? Which for the oils?
Describe the differences between the four samples, and the relationships between them. Be
specific, and discuss the different components of each sample.

3. What measurements are the same for (+) and (-) carvone? Which ones are different?

4. Explain the differences between data (odors, GC scans) for spearmint and caraway oils.
Explain the differences in odor based on the GC data.

5. Explain why the retention times for both carvone isomers are the same.

6. The toxicity of (+)-carvone in rats is about 400 times greater than that of (-)-carvone.
Propose a possible reason for these differences. How do you account for the difference in
these toxicities?
 27

Name___________________________________Lab day/time__________________
Week 9: Simple and Fractional Distillation
Chemistry 2400L, Spring 2023
PRELAB:
Read the Experiment: “Simple and Fractional Distillation” (Part A only).
Read about the following techniques: “Physical Constants of Liquids; The Boiling Point
and Density” (Part A only), “Simple Distillation”, and “Fractional Distillation” (Part A
only).
Prepare a lab procedure using Turnitin (at least 24 hours before lab), and bring a printed
copy of your procedure to lab.
Procedure:
Follow the procedure Experiment: “Simple and Fractional Distillation” (Part A only) in the
text. We will not be collecting a samples at 1.0 & 4.5 ml for GC analysis. Be aware that we
are using the macro glassware (14/20 long joints) with the exception of the 10 mL flask, and
that the glassware must be assembled using Kemclamps, lying flat on the table. Obtain your
instructor's permission prior to beginning heating. Follow all blue cautionary notes in the text,
make sure you use a boiling stone, and discard the final organic material in the non-
halogenated waste container. Both lab partners will perform the simple, followed by fractional
distillations as a team, using the same sample (fill the graduated cylinder back up to 7 mL) for
the fractional distillation as for the simple distillation.
 28

Data Table:

Simple Distillation Fractional Distillation

mL Temp (deg C) mL sample Temp (deg C)
sample
0.5 0.5
1.0 1.0
1.5 1.5
2.0 2.0
2.5 2.5
3.0 3.0
3.5 3.5
4.0 4.0
4.5 4.5
5.0 5.0
5.5 5.5
6.0 6.0
6.5 6.5

Data Analysis and Questions:

1. What is the likely boiling point of the lower boiling component? _______( o C) (based only
on your data, not based on the list of unknowns)
2. What is the likely boiling point of the higher boiling component? _______(o C)
3. Identify the two unknown compounds in your mixture by comparing your boiling points to
the “List of possible unknown liquids” (located in your text at the end of Experiment:
“Infrared Spectroscopy and Boiling Point Determination.”
 29

On the grid below, plot the data obtained for the distillations (mL collected on the x-axis, and
Temp on the y-axis). Plot data for both simple and fractional distillation on the same graph,
using different colors or symbols.

125

115

105

95

85

75

65

55

0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0
Volume distilled (ml)
1. What does your graph tell you about the efficiencies of the two distillation methods?
(e.g. which would be better at completely separating your two components)?

2. What is the purpose of boiling stones?

3. What errors would be introduced in the data, if the thermometer bulb were placed too
high in the distillation column?

4. Why is it dangerous to attempt to carry out a distillation in a completely closed

apparatus, one with no vent to the atmosphere?

5. Under what conditions can a good separation be achieved with a simple distillation?
 30

Name: Lab day:

Week 10: Infrared and Ultraviolet-Visible Spectroscopy

Chemistry 2400L, Spring 2023
Reading: Read and review topics on Infrared Spectroscopy. For reference, see the
Technique on IR spectroscopy in the Pavia laboratory text (Technique 25 in the 5th edition);
the sections on IR spectroscopy in your lecture text (McMurry, sections 12.-12.8, Karty Ch.
16); and the many spectroscopy links on the Canvas laboratory web site.

To turn in week 9:
Find and print one reference spectrum for one of the compounds listed below. Use sources
such as the NIST Webbook or Sigma-Aldrich site on the “External Links” on Canvas for the
lab course, to find this spectrum. Assign as many non-fingerprint region peaks as possible.
Turn these in with your name on them.

Choose one from this list:

Methyl benzoate
Acetophenone
2-Methyl-2-propanol
Chlorobenzene
Cyclohexanone
n-butyl amine
Anisole
Phenol
Aniline
Benzyl alcohol
Benzoic acid
Benzamide
 31

Name: Lab day:

Chemistry 2400L
Week 12&13 NMR Spectroscopy
PRELAB:
Read in McMurry (lecture text) Sections 13.1-13.13, or Karty Ch. 17. Familiarize yourself also
with Pavia, et al. (lab text) Techniques 25-27.

There is no written procedure this week.

PRELAB Week 9:
Review reading assignment from week 3: (McMurry, sections 13.1-13.13)
There is no written procedure this week.

During Lab Week 10:

--Laboratory: We will be doing NMR practice problems as a group.
--Afterwards you will be assigned one organic “unknown” sample per pair of students. You
will use this IR spectrum in combination with NMR spectra to identify your unknown.
--After lab: complete the remaining “paper and pencil” spectroscopy problems and your
assigned unknown, on the pages that follow (due Week 12).

Tables and figures:

Infrared spectroscopy (IR), stretches/bending frequencies:
1. Figure 25.13, Pavia (p. 544 Signature, p. 848 4th ed, p. 876 5th ed.)
2. Table 25.1, Pavia (p. 547 Signature, p. 851 4th ed.; p. 879 5th ed.)
3. Table 12.1, McMurry

Proton nuclear magnetic resonance (HNMR) chemical shifts and splitting patterns:
1. Figure 13.17, McMurry
2. Table 26.1. Pavia (p 906 5th ed.)

“Paper and pencil” problems begin on the following page”

 32

1. a. Draw the structure of benzyl methyl ketone and assign all of the peaks that
you can to the IR spectrum shown below.

b. Below is the HNMR spectrum for benzyl methyl ketone. Draw the hydrogen
atoms on the structure and label all protons with letters corresponding to the
peaks in the NMR spectrum below.
 33

2. An unknown compound has the formula C2H5I, and gives the IR and proton NMR spectra
shown on the next page.

a. From the formula, the unknown has ______ units of unsaturation.

b. From the IR spectrum (and considering the formula) the following functional groups are
probably present in the unknown:

c. From the proton NMR spectrum, the number of unique protons present is:

d. List the two sets of peaks in the NMR spectrum by chemical shift and intensity.

Chemical Shift Intensity (integral)

e. Proposed structure of the unknown:

f. Looking at the structure you drew in part (e), predict which functional groups you expect to
see in the IR spectrum.
 34

g. Looking at the structure you drew in part (e), fill in the chart in part (d) the expected
chemical shifts and expected intensities in the proton NMR spectrum.

h. "Recheck": does the data you generated in parts (f) and (g) agree with the observed data
recorded in parts (b) and (d)? If not, you need to revise your structure!

Proton NMR spectrum

3. An unknown compound with the

formula C8H8O2 gives the IR and
NMR spectra on the next page.
a. From the formula, the unknown has
______ units of unsaturation.
b. From the IR spectrum (and
considering the formula) the
following functional groups are
probably present in the unknown:

c. From the proton NMR spectrum, the number of unique protons present is:
d. List the sets of in the NMR spectrum below by chemical shift, and intensity (leave the last two
columns blank for now):

Chemical Shift Intensity Expected chemical shift Expected intensity

e. Propose a structure of the unknown:(draw next to the spectra)

f. Looking at the structure you drew in part (e); predict which functional groups you expect to see in
the IR spectrum.
 35

g. Looking at the structure you drew in part (e); fill in the chart in part (d) the expected chemical shifts
and expected intensities in the proton NMR spectrum.

h. "Recheck": does the data you generated in parts (f) and (g) agree with the observed data
recorded in parts (b) and (d)? If not, you need to revise your structure!

Proton NMR spectrum

 36
4. The two spectra below correspond to 2-butanol (CH3CH2CH(OH)CH3) its isomer, 2-methyl-
1-propanol ((CH3)2CHCH2OH). Draw these two isomers, and assign the correct
spectrum to each isomer. Explain what spectral data you used to reach your conclusion.
 37
Draw a structure corresponding to each unknown consistent with the formula and spectra
given. Follow the steps in problems 2 and 3, but include also the observed and expected
multiplicities (peak splitting) for the NMR spectra.

5a. C10H14

Units of unsaturation:

IR spectrum

HNMR spectrum

5.b. C4H6Cl2
Units of Unsaturation:
 38

HNMR Spectrum

5c. C8H10O
 39
Units of Unsaturation:

IR spectrum

HNMR Spectrum

5d. C4H8O2
Units of
Unsaturation:
 40

HNMR spectrum

6. Unknown. Please attach the NMR and IR spectra (or copies) to this report. Draw the
assigned structure of your unknown on each spectrum. For full credit, you must assign as
many peaks as possible in the IR spectrum, and all peaks in the NMR spectrum by writing on
the spectrum. (See figures 25.22-25.37 in Pavia for examples of correctly labeled IR spectra
(pp.550-561 in the Signature Edition, pp. 854-866 in Hardbound edition); AND Figure 26.25
for a correctly labeled proton NMR spectrum p. 595 in the Signature Edition, p. 898 in the
Hardbound edition). Make a photocopy of the IR run by you and your partner so that each
partner has a copy to turn in.
 41
a. Unknown number:
b. Formula:
c. Units of unsaturation:

d. The structure of my unknown is:

e. EXPLAIN HOW YOU ARRIVED AT YOUR ANSWER

 42
Laboratory Handout for Week 14
Crystallization
Chemistry 2400L, Spring 2023
Read the Experiment: “Crystallization” (Parts A, A-optional, and D).
Read about techniques: “Crystallization”, “Filtration” (sections about Gravity Filtration,
Filter Paper, and Vacuum Filtration), and “Physical Constants of Solids: Melting Points”
(skip section about The Thiele Tube).
Complete the prelab procedure using Turnitin (at least 24 hours before lab), and bring a
printed copy of your procedure to lab.
Calculate the amount of boiling ethanol needed to dissolve the sulfanilamide, and the amount
of sulfanilamide remaining dissolved at zero deg C. (prelab calculation). Fill in the answers
below.
Minimum amount of boiling ethanol needed: ml
Expected amount of sulfanilamide remaining at zero degrees: g
Show your calculations in the space below

PROCEDURE:
Complete the steps for semi-microscale crystallization of impure sulfanilamide, including
concentration of the mother liquor (the “optional” section). If the mother liquor has
evaporated, use a small portion of hot ethanol to transfer the residue in the filter flask into a
test tube, then concentrate to dryness. Make sure you record masses and melting point
ranges for all three solids. The keys to a successful crystallization is to quickly but carefully
 43
add a minimum amount of boiling solvent to dissolve the solid, then letting it cool slowly to
room temperature before cooling, without agitation.

MAKE SURE YOU OBTAIN AN INSTRUCTOR'S SIGNATURE NEXT TO THE DATA, AFTER OBTAINING
YIELDS AND MELTING POINTS, BUT BEFORE YOU DISCARD YOUR SAMPLES IN THE WASTE BOTTLE!
PROCEDURE (continued)
Melting point exercise (Part D).
1. Pack two tubes with your assigned unknown. Make sure to record the number/letter of
your unknown.
2. Determine the precise melting point range of your unknown in two trials.
3. Choose at least two likely identities for the unknown, from the samples provided.
4. Carefully mix crushed samples of your unknown, and the suspected known in a 1:1
ratio.
5. Obtain an accurate “mixed melting point” for the mixture your prepared.
6. Repeat steps 4 & 5 for each known you picked and your assigned unknown, until you
are sure that you have assigned your unknown correctly. Record your assignment.

Safety/Waste Disposal: Dispose of the melting point tube and unused sample in the
indicated waste containers.
DATA AND QUESTIONS:
CRYSTALLIZATION:
Mass of Sulfanilamide used: g
Mass of isolated sulfanilamide from crystallization: g
Percent recovery (= [mass isolated (g) / mass used] * 100) % show calculations

Melting point range of the impure sulfanilamide: - oC

Melting point range of crystalline sulfanilamide: - oC

Literature melting point: (source of data: )

Mass of sulfanilamide obtained from mother liquor: g
o
Melting point range of sulfanilamide obtained from mother liquor: C
 44

ADDITIONAL QUESTIONS
1. Why is the recovery of the first crystals less than 100%? Is the amount of material from
the crystals plus the mother liquor crystals 100%? Why or why not?

2. Which is purer, the original crystals, or the material isolated from the mother liquor? How
can you tell?

3. Using what you know about polarities of ethanol and sulfanilamide (draw their structures),
explain why ethanol is a good solvent for this crystallization.

4. Create a graphic representation of the steps you used to purify the sulfanilamide sample
via crystallization. This may be in the form of a flow chart, to show steps and what’s
removed at each step, or a series of diagrams.

Melting Point Data and Analysis for unknown

1. Unknown number/letter:
2. Approximate melting point of your sample:
 45
3. Exact melting Range of your sample: - oC, e.g. start point-end point
oC.
o
4. Mixed melting point with: , melting range: C
o
5. Mixed melting point with: , melting range: C
6. My unknown is: (chemical name)
7. Explain what effects each of the following improper packing techniques for the melting
point tube would have on the observed melting point range: (a) too much sample; (b) sample
packed too loosely.

8. What two effects does adding an impurity have on the melting point range of a compound?
 46

Name: Lab day:

Week 15: Reactivities of Some Alkyl Halides
Chemistry 2400L, Spring 2023

PRELAB: Read Experiment: “Reactivities of Some Alkyl Halides.”

Complete the online prelab procedure using Turnitin (at least 24 hours before lab), and
bring a printed copy of your procedure to lab.
SAFETY
1. All of the alkyl halide reagents should be handled in the hood. Many of these compounds
are considered to be either carcinogenic or eye and skin irritants; therefore these reagents
should be handled with considerable care. Avoid inhalation and contact with your skin.
2. Some care should be exercised when using the silver nitrate/ethanol solution. Although it
is not particularly toxic, skin contact may result in the formation of brown patches on the skin.

PROCEDURE
You will be running tests on the reactivity of a series of alkyl halides under both S N1
and SN2 reaction conditions. It should be noted that you will require nine clean and dry test
tubes for this experiment, and run the experiments in parallel. If you need to, you may use a
small quantity of acetone to aid in drying the test tubes before each reaction. Tests will not be
run for bromocyclopentane. Note that all wastes for these chemical tests must be placed into
the halogenated waste container. In addition, please use the droppers provided with each
reagent bottle to avoid cross contamination of reagents.
Record your results as dense precipitate, cloudiness, or no precipitate/cloudiness, as
well as the time needed to see this result, and be sure to indicate if heating was necessary
to obtain this result (only heat the tubes that don’t react at room temperature).
 47

Observations for Part A: Sodium Iodide in Acetone.

Deg of Test Alkyl Halide Heating Observations Time

substituti Tube ? (Y/N)
on*
1 2-chlorobutane

2 2-bromobutane

3 1-chlorobutane

4 1-bromobutane

5 t-butyl chloride

6 crotyl chloride

7 benzyl chloride

8 bromobenzene

9 bromocyclohexa
ne
*primary (1o), secondary (2o), tertiary (3o), allyl/benzylic, or aryl
 48

Observations for Part B: Silver Nitrate in Ethanol.

Deg of Test Tube Alkyl Halide Heating? Observations Time

substituti (Y/N)
on*
1 2-chlorobutane

2 2-bromobutane

3 1-chlorobutane

4 1-bromobutane

5 t-butyl chloride

6 crotyl chloride

7 benzyl chloride

8 bromobenzene

9 bromocyclohexa
ne
*primary (1o), secondary (2o), tertiary (3o), allyl/benzylic, or aryl

Additional Questions:

1. Rank in relative order the reactivity of 1˚, 2˚, 3˚, allylic/benzylic and aromatic halides in the
sodium iodide/acetone test. Briefly explain the reason for this difference in reactivity.
 49

2. Rank in relative order the reactivity of 1˚, 2˚, 3˚, allylic/benzylic and aromatic halides in the
silver nitrate/ethanol test. Briefly explain the reason for this difference in reactivity.

3. Compare the reactivity of 2-bromobutane and 2-chlorobutane in both tests. Which is more
reactive in each test? Why?

4. Why is benzyl chloride reactive in both tests, while bromobenzene is not?