CHEM 2924/2214 SPRING 2016 Honors/Majors Organic Laboratory II

Lab Report Instructions for Expt 11C: Isolation of a Natural Product

by Steam Distillation
General Information
If in doubt, always follow the PreLab/PostLab Template Format (see also Tiana Van sample
Lab Report on Blackboard).
Specific Information for Experiment 11C
Your report will consist of the following sections. Please put them in the order as indicated in the
PreLab/PostLab Document. Use the headers listed below to designate each section, except for
the Title.
Title: The title of the experiment, the experiment number, and the date that the experiment was
performed in lab. This information is identical to that required in your pre-lab write-up. The title
should be complete and accurate.
Objective: List the goals, or the purpose, of the experiment. This information is identical to that
required in your pre-lab write-up.
Experimental Procedure: Please include a reference to the source of the procedure, as well as
any modifications that were posted on Blackboard in the proper format. If necessary, these
statements should be followed by a list of any additional modifications to the
experimental procedure. It is very important that you document any changes to the procedure
in your lab notebook at the time of the experiment, and include them in your report. This section
may help to explain unexpected results, for instance.
Experiment 11C was followed as described in Mayo, pages 242-244.
Reaction Scheme: As this experiment does not involve a chemical reaction, a full scheme is not
applicable. Simply draw the structure of the natural product in Chem Draw (or ACD), and
include the name below the structure.
Using any form of electronic copy and paste to reproduce directly a reaction scheme
from any source, including the printed or electronic lab textbook, is a violation of the
Academic Integrity policies of this course. All parts of your lab report text, schemes, tables,
etc. must be done by you. You may draw the reaction scheme using Chem Draw or ACD.

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Safety Data: Put the NFPA and hazard identification data in the appropriate section in the
PreLab/PostLab Template
Data and Results: Organized in three parts as shown below. As with the Reaction Scheme, this
section will be much more simple than usual.
Data and Results Table
Give original data and calculated values in an organized tabular format.
Include appropriate units and pay attention to significant figures.
Data may differ slightly from that reported in your pre-lab write-up. You must report and use
the actual values in your calculations. In this way, your final results and conclusions match
what you actually did in the experiment, not what you intended to do in your pre-lab.
Below is a sample layout for the Data and Results Table. Modify the PreLab/PostLab template to
include this Table. As with the Reaction Scheme, using any form of electronic copy and
paste to reproduce directly a data table from any source, including the printed or
electronic lab textbook, is a violation of the Academic Integrity policies of this course.
Stick cinnamon
Mol. Formula
Amount used (g)

Cinnamaldehyde
?

Amount isolated
(mg)

Molar Mass

Lit. bp (C)

Observations
Data includes all relevant observations, such as heat evolved, initial color and color changes,
precipitate formation, state of product, etc. Observations should be listed in bulleted, complete
sentences. For this experiment, you should include the temperature range of distillate collection,
the amount of distillate collected, any odors, as well as the appearance of the distillate and the
final isolated product. Dont forget that you must put the observations/results in the
observation/results section of the PreLab/PostLab template after recording them in your
notebook during the lab period.
Calculations
For any calculated values, show your work. This part does not have to be typed, and you may
prefer to leave space in your document and enter the calculations by hand. Please be as neat as

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possible. Note that for this isolation experiment, the % crude cinnamaldehyde calculation differs
from a typical reaction % yield because a theoretical yield was not determined.
1) Yield of crude cinnamaldehyde = (final weight of test tube + product) (weight of test tube)
2) % Crude cinnamaldehyde isolated from the original sample of cinnamon (differs from a typical
reaction % yield because a theoretical yield was not determined)
Questions: Answer the following questions. Be as complete as possible, and always explain
your reasoning.
1. The steam distillation was run long enough to be able to isolate a measurable quantity of
cinnamaldehyde, but not all the way to completion. (in other words, it is likely that you did not
extract all of the cinnamaldehyde from the cinnamon).
Which of the following results would indicate that all of the cinnamaldehyde contained in the
cinnamon sticks had been isolated by the steam distillation process? For each answer(s)
selected (there may be more than one correct answer), please provide a brief explanation.
a)
b)
c)
d)
e)

The steam distillate collected in the Hickman still was cloudy.

The steam distillate collected in the Hickman still was clear.
The distillation pot (the 10-mL round-bottomed flask) was dry (no liquid remained).
The steam distillate vapor temperature was 99.0 C
The steam distillate vapor temperature was 100 C.

2. Draw, and name, all of the possible stereoisomers of cinnamaldehyde.

3. The technique of steam distillation is possible because essential oils like cinnamaldehyde are
NOT miscible with water to any great extent. Discuss the structural features of
cinnamaldehyde that are responsible for its low water solubility, and why (incorporate relevant
intermolecular forces in your answer).
4. An IR spectrum of cinnamaldehyde is found on page 4. What absorption bands would you
look for in the IR spectrum of your isolated product to confirm its identity? You should begin by
identifying the functional groups in the molecule. Cinnamaldehyde contains an aromatic ring,
an alkene, and an aldehyde, all in conjugation.
a) From the IR spectrum, select three specific absorption bands (in cm-1, from the absorption
band peak picking) that inform you about one or more of the functional groups in
cinnamaldehyde.

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b) For each of your answers in part (a),

identify the specific bond vibration
attributed to the observed absorption band
(for example, alkene C-H stretch).
Works Cited: Full references for the
experimental procedure(s) in the following
format (see also PreLab/PostLab template and
the sample lab report by student worker Tiana
Van on Blackboard:
1. Mayo, D. W.; Pike, R. M.; Forbes, D. C.
Microscale Organic Laboratory with Multistep
and Multiscale Syntheses, Custom 6th ed.;
John Wiley & Sons, Inc., 2014; pp. 238-244.