Edit 1-5-2024 by Margaret Henderson
University of Washington - Tacoma
Organic Chemistry I (TCHEM 261)
Integrated Alkene Synthesis - Distillation Lab
Student Version
OVERALL INTRODUCTION
In this lab, you will first learn the technique of distillation, comparing the effectiveness of
simple versus fractional distillation by analyzing gas chromatography data. You will then use
the distillation technique to isolate the alkene products from an alcohol dehydration reaction.
GC data will allow students to determine whether this reaction proceeds according to
Zaitsev’s rule, as predicted by theory.
PART 1 – DISTILLATION
INTRODUCTION
Distillation is an inexpensive and relatively simple technique used to separate or purify
mixtures of liquids, determine boiling points of liquids, and separate liquids from solid
contaminants. Chemists often use this method to separate homogeneous solutions of two or
more liquids. In industry, distillation is used to separate the economically important
components of fossil fuels including natural gas, gasoline, kerosene, heating oil, and
lubricants. In the food industry, distillation is used to concentrate the alcohol in wines and
other beverages obtained from the natural fermentation of fruits and vegetables. Both of these
economically important processes separate liquids by differences in their boiling points.
Distillation can also be used to isolate a volatile product from a reaction mixture. For
reactions with an intermediate equilibrium constant, distillation can be used to shift the
equilibrium towards a greater yield as per Le Chatelier’s Principle.
In practice, liquids can be separated by simple or fractional distillation. A good Khan
Academy video explains this process: [Link]
prep/mcat/chemical-processes/separations-purifications/v/simple-and-fractional-distillations
and is required viewing in the preparation section. Basically, as a mixture of liquids is heated,
the vapors produced will be richer in the more volatile component, which is the one with the
higher vapor pressure. If these vapors rise and then re-condense, the condensed liquid will be
richer in the lower-boiling component. The phase diagram in Figure 1 shows this process.
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Figure 1: Change in Mole Fraction of Components During Distillation of a Mixture
In simple distillation, a liquid mixture is heated, travels up into a distillation head, then
condenses in a condenser. Figure 2, below left, shows a simple distillation set-up. Figure 3,
below right, shows a fractional distillation apparatus. In fractional distillation, the vapors
travel through a longer column which is usually packed with steel wool, glass beads, or some
other inert material designed to provide lots of surface area on which repeated cycles of
vaporization and condensation occur. Each time vaporization/condensation occurs, the
resulting liquid is further enriched in the component with the lower boiling point.
Fig. 2: Simple distillation apparatus Fig. 3: Fractional Distillation Apparatus
As a mixture distills, the composition of the distillate changes, so the temperature of the
distillate also changes. A plot of the temperature as a function of the volume of distillate
collected is known as a distillation curve and can be used to determine what liquid is being
collected at different points in the distillation. Figure 4 shows typical distillation curves for
both simple and fractional distillations of a mixture of liquids.
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Fig. 4: Theoretical Distillation of a Mixture of Two Liquids
Distillation Curve
160
140
120
Temperature
100
80
60
40
20
0
0 1 2 3 4 5 6 7 8
Distillate Volume
Fig. 5: Actual Fractional Distillation Curve for a Curves for a Mixture of Two Liquids
In this experiment, you and your partner will be assigned one of the two distillation methods
and an unknown mixture of organic solvents. Using the semi-microscale glassware kit in
your organic drawer, you should separate the 8-ml unknown sample. Another team will distill
the same mixture using the other distillation method. These two teams will them share their
data with one another so that they can compare the efficacy of simple versus fractional
distillation.
After comparing the quality of the two methods by constructing a distillation curve, you will
also submit your samples for gas chromatography (GC) analysis. That, along with the boiling
points obtained from the distillation curves, should allow you to identify the pure unknowns.
Edit 1-5-2024 by Margaret Henderson
PREPARATION
1. Read the Whole Lab, especially the post-lab write-up instructions.
a. Watch the Khan Academy video online. [Link]
prep/mcat/chemical-processes/separations-purifications/v/simple-and-fractional-
distillations . Please note the following differences in procedure from the
video: I) We will use a hot plate and aluminum block to heat the distilling flask
instead of an oil bath or heating mantle. II) We will pack the fractional column
with steel wool instead of beads or stars.
b. In Section 5 of the Nichols lab manual, read the Overview (p.232) about
distillation. I also recommend a quick read through uses of distillation (p. 235).
Section V.2 B3 (that’s 5.2 B3) on distillation theory (p. 238-239) is helpful. Look
at figure 15. 13 on p. 238. Section V.2 C (p. 244- 253) covers the practical aspects
of distillation.
c. Section 5.2 B covers the theory of distillation. You learned about Raoult’s and
Dalton’s Laws in Gen Chem, but that has been a while ago, so a review may be
helpful. This is pages 235-238.
d. Watch this video about Gas Chromatography: [Link]
prep/mcat/chemical-processes/separations-purifications/v/gas-chromatography
2. Learn or Review any concepts or skills you are not confident about applying during lab.
A suggested source to review the concepts of vapor pressure and boiling point is:
[Link]/~samal/269/[Link]
3. Prepare your lab notebook as described below.
LAB NOTEBOOK Set-Up
Clerical Information
• Title – Use the one given for this lab.
• Date work done
• Your Name
• Name of Lab Partner on that date/for that lab
• Be sure to also enter the lab in your Table of Contents.
Objective – After reading the entire Part 1 of this lab, identify and write down the objective of
the lab in your notebook. The objective is the question or questions your data will hopefully
allow you to answer.
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Hypothesis – For this lab, please write a hypothesis about which type of distillation will be most
effective at separating your unknown.
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Physical & Chemical Properties Table – Use the format below. Be sure to include your
solvents and reagents. Think carefully about what physical properties are most relevant and ones
you might need to know during lab.
Possible unknown components of the liquid mixtures are acetone, cyclohexane,
ethylbenzene, hexane, heptane, octane, and toluene.
Chemical Use/Purpose Relevant Physical Properties Hazards Response to
Name in THIS lab hazards
? ? ?
Chemical Reaction Equation – N/A for Part 1 of this lab.
Complete the Pre-Lab Worksheet on plain paper (NOT in your lab notebook)
Experimental Plan – Use the Experimental directions below to write a procedure for yourself in
your lab notebook.
• Bullet points or flowchart preferred
• Lab Guide not allowed in lab (but I will have a reference copy up front)
Turn in the copies of your lab notebook pages up to this point, along
with the Pre-Lab Worksheet prior to lab at the time set by your
instructor.
Data & Observations – Create pages in your notebook to record all the data you will collect.
Label spaces to remind you what you need to write down. Hint: Should you record your
unknown code? Do Not remove or turn in these pages.
After preparing your lab notebook, please take the on-line pre-lab quiz to ensure that you
have a solid background for the investigation you will carry out in this lab. If you miss
questions in the pre-lab quiz, follow instructions for reviewing and redoing the quiz.
Edit 1-5-2024 by Margaret Henderson
Experimental Directions
Set up either a simple or fractional distillation apparatus as assigned. Use a hot plate with the
aluminum heating block as the heat source. Place 2 boiling chips in the distilling flask, and add a
known volume of your unknown mixture. If you have been assigned fractional distillation,
loosely pack your air condenser with stainless steel cleaning pad material (instructor wil
demonstrate this at the beginning of lab. You should also insulate your air condenser with the
Tygon jacket material provided. Have tared and labeled collection containers (the conical vials)
ready. Turn on the cooling water and begin heating. You will need to track temperature and
volume of condensate collected. It can be useful to note time as well. Record the temperature
and volume at frequent intervals. Collect different boiling fractions in separate vials. Continue
until 0.5-1.0 mL of liquid remain in the distilling flask. Do not boil the flask dry – it will crack.
Things to Watch Out For In Distillations:
(1) The thermometer is positioned incorrectly - this leads to observed temperatures which are
incorrect. The top of the thermometer bulb must be even with the bottom of the side arm on the
distilling head, or a little lower. It must not touch the metal packing or the glass apparatus.
(2) Be sure your water lines go IN the lower end of the condenser jacket and come OUT from the
higher connector.
(2) Distillation is too rapid due to excessive heating - this leads to a poor separation. Start over if
this occurs. If this happens with your unknown, do not dispose of the liquids. Simply recombine
all liquids and redistill the mixture.
(3) Not enough heating - this leads to reflux (a condition in which the vapors condense and
return to the distilling flask) instead of distillation. Supply enough heat so that the distillation
proceeds steadily at a rate of about one drop per 20 - 30 seconds.
(4) After the low-boiling fraction has distilled, the distillation may slow or stop and the
temperature may fluctuate or drop - this is because more heat is required to distill the higher-
boiling fraction. Increase the heat below the distilling flask so that the distillation proceeds at a
rate of one drop per 20 - 30 seconds. This is more likely to happen with the fractional distillation
because of the longer path. It is advisable, especially if the lab is drafty, to insulate the distilling
column in the fractional distillation.
(5) The distilling column is packed too tightly with metal sponge - this leads to a situation known
as flooding of the column, in which a plug of liquid collects in the column. Distillation will be
severely hampered in such a case.
(6) The distilling column is packed too loosely - a poor separation results.
(7) With this equipment, a measured BP may be considered to be reliable only after the
temperature has leveled off and the distillation rate is about 1 drop per 20-30 seconds. Even then
the measured BP may be a few degrees off.
(8) Liquid boils in the flask but none is collected in the vial. This may be due to a leaking
connection – check them.
Edit 1-5-2024 by Margaret Henderson
Submitting Samples for GC
Small vials will be supplied for GC samples. You should submit two samples at a minimum.
The first should be the lower boiling component and the second the higher boiling component. If
you wish, you may submit one additional sample if you feel the need to analyze an additional
fraction of your distillation. A Gas Chromatogram of your original mixture will be provided..
Minimum sample volume to submit is 0.5 mL. To label samples, use a sharpie to write directly
on the vials. NO TAPE! Label samples clearly with lab section code (AA, AB, BA, or BB,
etc.), station number and atomic number, and part of distillation sample is from (ie low temp,
high temp, int. temp). Do NOT put initials or names on vial.
Lab Section Code (A or B) Lab station
number
Lab station number
5A 11B
22 & 31 5 & 17
LB HB
Brief title
Brief title
Each person’s
atomic number
Figure 6: Sample GC Labels for lower-boiling and higher boiling fractions collected. Label on
left is the lower boiling (LB) sample submitted by a team in Section AA who worked at Station
#5 and are numbers 22 & 31 on the class list. Label on right is the higher boiling (HB) sample
submitted by a team in Section AB who worked at Station #11 and are numbers 5 & 17 on the
class list.
Submit Carbon copies of Data & Observation Lab NB pages before leaving lab.
Edit 1-5-2024 by Margaret Henderson
PART 2 – ALKENE SYNTHESIS
INTRODUCTION
One method for preparing alkenes is dehydration of alcohols in the presence of strong acids and
heat. This is a -elimination reaction. In lecture, we were told that the reaction is both
regioselective and stereoselective. In this lab, we will be investigating to see if the reaction really
is regioselective and really follows Zaitsev’s Rule, producing the more highly substituted alkene
as the major product. The dehydration reaction is reversible, so the reaction equilibrium can be
pushed towards the product by distilling the low boiling point alkenes from the high boiling
point reaction mixture as the alkenes are formed. The distillation does not separate the alkenes.
The presence of the products will be verified and quantified by gas chromatography analysis.
The main reaction for this activity is shown below:
Figure 1. Reaction of tert-amyl alcohol (2-methyl-2-butanol) with sulfuric acid
producing a mixture of alkenes.
PREPARATION
1. Read the Whole Lab, especially the post-lab write-up instructions.
2. Learn or Review any concepts or skills you are not confident about applying during lab.
Review the alcohol dehydrogenation/elimination reaction from Smith if necessary. You should
be confident in doing a simple distillation (Part 1). Note that none of the pictures in various texts
and videos look exactly like our semi-microscale set-up. A better diagram of ours is shown
below.
3. Prepare your lab notebook as described below.
Edit 1-5-2024 by Margaret Henderson
LAB NOTEBOOK Set-Up
Clerical Information
• Title – Use the one given for this lab.
• Date work done
• Your Name
• Name of Lab Partner on that date/for that lab
• Be sure to also enter the lab in your Table of Contents.
Objective – After reading the entire Part 2 of this lab, identify and write down the objective of
the lab. The objective is the question or questions your data will hopefully allow you to answer.
Hypothesis – For this lab, please write a hypothesis about whether or not the reaction follows
Zaitsev’s rule. Explain what evidence will allow you to answer this question.
Physical & Chemical Properties Table – Use the format below. Think carefully about what
properties will be useful to have at hand when you are running this reaction.
Chemical Use/Purpose Relevant Physical Properties Hazards Response to
Name in THIS lab hazards
xx xx xx
Complete the Pre-Lab Worksheet on plain paper (NOT in your lab notebook)
Experimental Plan – Use the Experimental directions below to write a procedure for yourself in
your lab notebook.
• Bullet points or flowchart preferred
• Lab Guide not allowed in lab (but I have a reference copy up front)
Turn in the copies of your lab notebook pages up to this point, along
with the Pre-Lab Worksheet prior to lab at the time set by your
instructor.
Data & Observations – Create pages in your notebook to record all the data you will collect.
Label spaces to remind you what you need to write down. Do not turn in the copies of these
pages
After preparing your lab notebook, please take the on-line pre-lab quiz to ensure that you
have a solid background for the investigation you will carry out in this lab. If you miss any
questions, follow the instructions given on how to review this material.
Edit 1-5-2024 by Margaret Henderson
Experimental Directions
Dehydration of t-amyl alcohol
These directions are written in “journal style” as opposed to lab direction (cookbook)
style (with the exception of the Helpful Hint box.)
The procedure was carried out in a semi-microscale distillation apparatus using the 10
mL round bottom distilling flask and the 5 mL vial as a receiving vessel. In a 10 mL
round bottom flask, t-amyl alcohol (2-methyl-2-butanol, 3.0 mL, __ moles) was
combined with H2SO4 (9M, 25 drops) and 2-3 boiling chips. The 10 mL round bottom
flask was then attached to the distillation apparatus, and the reaction and distillation
were carried out.
Helpful Hints:
• The product is very volatile, so pile the ice all around the receiving vial clear up to the
condenser.
• Start with the hot plate set to 4-5, but be ready to adjust up or down as needed.
• Be careful to think about what temperature the distillation must be stopped at!
After noting the volume of product collected, the product was transferred to a
reaction tube and washed twice with an equal volume of saturated NaHCO3. A clean,
dry pipet was used to transfer the alkene layer to a clean, dry test tube after the second
wash. (N.B. density of alkenes is 0.66 g/mL). Particular care was taken to NOT
transfer any of the aqueous layer into this dry test tube. The alkene layer was dried with
two pin-head-sized scoops of CaCl2. Care was taken to not shake the mixture enough
to mix any CaC2 into the liquid, or transfer any CaCl 2 with the alkene during decantation
into a clean, dry, labelled vial as this would clog the GC.
Bromine Test
The bromine test was carried out by placing 3 drops of a known alkene, 1-pentene or
cyclohexene, into one test tube and 3 drops of the supposed alkene layer into another
test tube. A third test tube contained 3 drops of the t-amyl alcohol. To each test tube, 1
drop of 5% Br2/CH2Cl2 was added and color changes or other evidence of a reaction
was noted.
Edit 1-5-2024 by Margaret Henderson
GC Sample Prep
The distillate was placed in a clean, dry GC vial and labelled as shown below.
How To Label the GC Vial
Lab station number 5B Lab Section Code (A or B)
Alkene
Brief lab title 15, 23
Each person’s atomic
number
When running the GC, it is often necessary to dilute the sample with a non-reactive
solvent with a clearly different GC retention time. Your lab instructor may give you
instructions about preparing a sample diluted in heptane.
Clean-up
• At the end of the experiment, dismantle, clean, dry and replace all equipment and
glassware in the appropriate drawer or cupboard.
• Discard the distillation residue (in the round bottom flask) and water washes in the
'acid waste' collector, CaCI2 solids in 'spent drying agent',
• Glassware that was used for acid or base must be rinsed with water first; acetone
does not dissolve acid or base.
• To remove non-polar chemicals or hasten the drying of wet glassware, rinse with a
minimal amount of acetone into the acetone waste collector.
Dry the acetone-rinsed glassware by blowing on it with a gentle stream of compressed
air.
Edit 1-5-2024 by Margaret Henderson
PART 3 – GAS CHROMATOGRAPHY
Please read section 2.5 – gas chromatography – in your Nichols Organic
Chemistry lab manual.
[Link]
chniques_(nichols)/02:_chromatography/2.05:_gas_chromatography_(gc)
We will spend time learning about GC during the third lab session for this lab.
Gas Chromatography: Interpretation of Result
The area of each peak in the gas chromatogram is proportional to its concentration.
Since retention time is not absolute, a standard sample is injected at the start of every
run, and the retention time (in minutes) and peak area (in uV*sec.) for a standard sample
(usually 2%-5% concentration) of a known substance is used to identify peaks and
calculate the concentration of the unknown sample. In this experiment, overall
concentration of sample is irrelevant, because we are using the GC to determine the
relative concentrations of the two alkene isomers.
Part 1 - Distillation Post Lab Write-Up
Post lab write-ups should be typed, double spaced, and submitted as a hardcopy.
DATA SUMMARY & PRESENTATION
1) Create a data table showing temperature, volume of distillate collected, and approximate
time using the simple distillation data you or your collaborating team collected. Include the
code of your unknown. Attach
2) Create a second data table showing temperature, volume of distillate collected, and
approximate time using the fractional distillation data you or your collaborating team
collected. Include the code of your unknown. Attach.
Edit 1-5-2024 by Margaret Henderson
3) Using the data tables above, create separate graphs showing each type of distillation curve
using EXCEL. This should be a scatterplot of temperature as a function of total volume of
distillate collected. Plot the volume in 0.5 mL increments on the x-axis and the temperature on
the y-axis. Best fit lines should be added either using the line-fit function or by hand. ASK if
you don’t understand what kind of graphs are being requested. Attach.
4) Fill in tables below showing your GC results (retention times and peak areas). Attach your
chromatograms produced by the samples from your distillation of a mixture of liquids, with
peaks labelled, to this lab write-up.
Simple Retention Area % component Retention Area % component
Distillation Time for Under 1 out of total Time for Under 2 out of total
Samples Peak 1 Peak 1 of both Peak 2 Peak 2 of both
components. components.
Initial
Mixture
Lower
Boiling
Component
Higher
Boiling
Component
Mid-
boiling
sample?
Fractional Retention Area % Retention Area %
Distillation Time for Under component 2 Time for Under component 2
Samples Peak 1 Peak 1 out of total Peak 2 Peak out of total
2
Initial
Mixture
Lower
Boiling
Component
Higher
Boiling
Component
Edit 1-5-2024 by Margaret Henderson
POST-LAB QUESTIONS ABOUT DISTILLATION
5) Look at the graph you made for a simple distillation. Using only this graph,
a. Can you identify a b.p. of the lower boiling component? If so, what is it?
b. Can you identify a b.p. of the higher boiling component? If so, what is it?
6) Look at the graph you made for fractional distillation. Using only this graph,
a. Can you identify a b.p. of the lower boiling component? If so, what is it?
b. Can you identify a b.p. of the higher boiling component? If so, what is it?
7) Did your simple or fractional distillation give clearer temperature plateaus?
8) From your best distillation data (do not consider the GC data), what would be
reasonable identities of the components in this mixture? Explain using data values.
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9) GC Data Analysis
a. Based on the retention times obtained from the GC, what do you think the
components of your mixture are? Explain uses data values.
b. Do the identities determined from the GC data match the identities determined from
your best distillation data? If not, which method do you think is more reliable? Explain why
it might be more reliable.
10) Composition of Fractions
a. Use your GC data from Question 4) to complete the following table.
Sample % Component A % Component B
(lower boiling) (higher boiling)
Initial mixture
Simple Distillation Low boiling sample
High boiling
sample
Fractional Low boiling sample
Distillation High boiling
sample
b. Based on these results, which type of distillation gave the best separation of
components as reflected in enrichment compared to the initial mixture? Was your hypothesis
upheld or disproved? Explain your answer.
Edit 1-5-2024 by Margaret Henderson
Part 2 - Alkene Synthesis Post Lab Write-Up
Post lab write-ups should be typed, double spaced, and submitted as a hardcopy.
DATA SUMMARY
11. Your data submission consists of the following:
a. The carbon copies of the lab notebook pages on which you recorded data &
observations for this lab (turned in at end of lab session.)
b. Attach the GC chromatogram(s) generated from your product sample with peaks
labelled with the identity of each peak and its area.
c. Create a table giving the mass and volume of your reactant and your product mixture.
Attach.
DATA ANALYSIS
12. Using the GC data, calculate the relative concentrations of each type of alkene produced.
Show your calculations.
13. Calculate the percent yield of total product. Show your calculations.
14. Answer the following questions by giving evidence and the conclusion you reached based
on that evidence. Please note: always state the evidence before the conclusion so the reader
can follow your reasoning and anticipate your conclusions.
a. What reaction are you expecting? Draw a chemical equation & mechanism for the
reaction you expect. Name the possible products. What testable chemical and physical
properties do these expected products have?
Edit 1-5-2024 by Margaret Henderson
b. What do you believe is the identity of the compounds you actually isolated from the
reaction mixture? Think carefully about what data you collected that would allow you to
identify the product or products you created.
c. Was the ratio of alkenes you found consistent with Zaitsev’s Rule? Remember to give
data and explain how it led to your answer to this question.
d. Did your data include any conflicting or unexpected results? If so, explain and suggest
further work that could be done to answer the question posed in this hypothesis.
15. Was distillation a useful technique in the synthesis of alkenes?
a. Did it separate the products from the starting material well?
b. Did this method give a good yield of product?
c. If the alcohol and acid had been refluxed with no distillation, then the left-over starting
material and alkene products separated by another method such as liquid-liquid extraction,
how do you believe that might have affected the yield? Explain.
REFERENCES
Macroscale and Microscale Organic Experiments, by K.L. Williamson, 5th edition, Chapter 5
