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Experiment #9: Elimination Reactions

(Wednesday, Nov. 12th Tuesday, Nov. 18th)
Part A: Design and performance of an elimination reaction
Part B: Interpretation of GC-MS Data and Intro to IR Spectroscopy
In Part A of this laboratory session you will work with your peers and your section instructor to design an elimination reaction
and workup, starting with meso-stilbene dibromide. This task will require your knowledge of laboratory techniques, as well as
experimental (lab) and theoretical (lecture) reaction considerations. The product(s) will be characterized by chemical tests,
thin-layer chromatography, infrared spectroscopy, and/or gas chromatography coupled with a FID or mass spectrometer (GCFID and GC-MS) analysis as appropriate. In Part B of this laboratory session you will carry out activities to improve your
understanding of data derived from gas chromatography (GC) coupled with a flame ionization detector (FID) or mass
spectrometer (MS), and infrared spectroscopy (be sure to watch the new video links below).

Textbook Reading:
G&M pg. 403-405 (alkynes)
G&M pg. 867-868 (Br2/CH2Cl2 and Bayer tests)
G&M pg. 196-206 (GC-MS reassigned)
G&M pg. 237-256 (infrared spectroscopy)
Jones 5th Ed. pg. 301-311 (elimination reaction)
Some Key Terms (in the context of this experiment):
elimination reaction (first order vs second order), side
reaction/product, gas chromatography (GC), mobile
phase, carrier gas, stationary phase, equilibrium
constant, mass spectrometry, molecular ion, parent ion,
isotopes, molecular weight, exact mass, mass
spectrometer (MS), flame ionization detector (FID),
infrared (IR) spectroscopy, absorption, functional group
Video Instruction:
View these videos as part of your pre-laboratory
preparation. Be aware that these videos will show you a
general technique/equipment but the compounds,
solvents, quantities, and exact equipment may not be
the same as those you will use in the laboratory. Use
these videos to become familiar with set-ups,
procedures, and concepts but think carefully about how
your experiment may differ from the video.
Recrystallization (re-assigned): (10 minutes each)
https://www.youtube.com/watch?v=XK0MZk3Q4jk
&feature=player_embedded#at=12
Note: The recrystallization video is re-assigned for you
to review the principles. You have carried out this
technique several times and you should be prepared to
perform it independently if needed.
Gas Chromatography (GC): (10 minutes)
http://www.youtube.com/watch?v=dffeiLgeKx8
Mass Spectrometry (MS): (10 minutes each)
http://www.youtube.com/watch?v=rBymrFzcaPM
http://www.youtube.com/watch?v=dq7xKVvXWew
http://www.youtube.com/watch?v=Ar1Zum1Phv8
http://www.youtube.com/watch?v=fr89hoF1QjE
Note: The GC video and the first two MS videos are reassigned, but the third and fourth MS video are new. It
is important that you understand how to identify/predict
the molecular ion, isotopes, and fragmentation patterns
(i.e. the signals that appear at lower mass than the
molecular ion).

Infrared (IR) Spectroscopy: (14 minutes)

https://www.youtube.com/watch?v=XIWc9eT476c
http://www.youtube.com/watch?v=FfI5BczOXQ8
Infrared (IR) spectroscopy:
IR spectroscopy is one of the oldest methods of
physical characterization of organic compounds, used
to establish the structure but usually not the purity of a
substance. At one time, organic chemists would analyze
many peaks in the IR spectrum, but when Nuclear
Magnetic Resonance (NMR) and MS data are available,
then the IR data are used primarily to determine the
presence or absence of key functional groups. Thus
only a relatively small number of absorption bands in
the IR spectrum need to be assigned. When analyzing
an IR spectrum, the absence of an absorption band can
be as informative as the presence of one (this will be
true of signals in NMR spectra as well, which we will
study in Experiment #10).
Pre-lab notebook preparation:
On a page of your notebook, include only (1) your
NYU N-number and (2) a complete arrow pushing
mechanism to convert meso-stilbene dibromide to 1,2diphenylethyne. You will submit one of these carbon
copies to your instructor at the start of the lab session. It
is important that you study the elimination mechanism
before your lab session. This page is the only required
notebook preparation (no chemical table, procedure, etc
required).
H
Br

Ph

Br
Ph =
Ph
H
meso-stilbene dibromide
?

Br
Ph
Ph
(E)-(1-bromoethene-1,2-diyl)dibenzene

Ph

Ph

1,2-diphenylethyne

Figure 1. Target elimination products, (E)-(1bromoethene-1,2-diyl)dibenzene

and
1,2diphenylethyne, starting from meso-stilbene dibromide.

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PART A:
In a continued effort to not only perform science, but to
think like scientists, you will be involved in an
increased degree of the decision making for this
experiment. To this point in the term we have learned
how to assemble common reaction set-ups, as well as
how and when to perform common purification
techniques. Further, you have learned how to assess
yield, identity, and purity of a recovered or synthesized
compound using various methods. Now you are going
to put that information to use as you will collaborate
with your instructor and peers to design an elimination
reaction, workup, and characterization scheme. You
will be using meso-stilbene dibromide as your starting
material (Figure 1) and you will need to take into
consideration several factors when planning your
experiment. Your instructor will help guide you through
some of the key decisions, but you should arrive at the
lab having though about the general scheme and how
you would get from the starting material to the product
in each reaction in Figure 1 (consider information
regarding reagents, equivalents, temperature, etc.). You
will carry out the reaction and workup procedure that
you will design.
Analysis methods.
In collaboration with your peers and instructor, you will
determine which methods of characterization will be
carried out. The product(s) will be characterized by
chemical tests, thin-layer chromatography, infrared (IR)
spectroscopy, and/or gas chromatography coupled with
a FID or mass spectrometer (GC-FID and GC-MS)
analysis as appropriate. Be sure that you understand the
these methods before you arrive at the laboratory (i.e.
know the difference in data that would be observed if
the starting material vs (E)-(1-bromoethene-1,2diyl)dibenzene vs 1,2-diphenylethyne were being
analyzed). It is important to learn both the usefulness
and the limitations of each technique.
Bromine in dichloromethane test. Place small amount
(~5 mg) of your product in a test tube and add 1 drop of
the premade bromine in dichloromethane (Br2/CH2Cl2)
solution. The Br2/CH2Cl2 solution should turn
immediately colorless if the product is unsaturated.
Adding more of the Br2/CH2Cl2 solution will change
the solution in the test tube from colorless into yellow.
Be sure to see the G&M textbook for details on this
chemical test, and think about the limitations of this
test.
Bayer test. Place a small amount (~5 mg) of your
product in the test tube. Dissolve it in 2 mL of 95%
ethanol and count the number of drops of the
permanganate solution added in order to make the
purple color persist. Compare this number of drops to
the number of drops added to the blank (2 mL of 95%
of ethanol) to reach the same purple color. Significant

difference in the number of drops is an indication of an

unsaturation. Be sure to see the G&M textbook for
details on this chemical test, and think about the
limitations of this test. Also, be sure to dispose of this
material in the special permanganate waste bottle.
Thin layer chromatography Analysis:
As you have been practicing, if appropriate you will
create TLC analysis conditions.
GC-FID and GC-MS Analysis (Sample preparation):
Sample preparation will depend on the workup
procedure that you used. Your section instructor will
advise you on how to prepare samples for GC analysis.
Note: it is vital that NO sample may be acidic or
contain ANY solid.
Infrared analysis (Sample preparation):
Your section instructor will advise you on how to
prepare samples for IR spectroscopy analysis.
Bulk Sample Submission (your remaining sample):
Deposit your sample in a pre-weighed vial and re-weigh
it to determine the mass of the sample. Clearly label the
vial with the following information:!
1) Your full name (first and last)!
2) Your section #!
3) Date!
5) Target compound name!
*A deduction of 5 technique points will be incurred if
the vial does not contain all of this information upon
sample submission. The same deduction will be
incurred if any information is incorrect or illegible.
!
PART B:
In Part B of the laboratory session you will carry out
activities to enhance your understanding of data derived
from gas chromatography (GC) coupled with a flame
ionization detector (FID) or mass spectrometer (MS),
and infrared spectroscopy. Instructions for Part B will
be provided during the laboratory session. Be sure to
study the instructional videos listed on page 1 of this
handout.
Postlab Assignment:
For this experiment you will not write a report. Instead
you will complete a postlab assignment that will be
distributed via NYU Classes (in the experiment folder)
after your laboratory session. Although you will not
write a report, your data and observations from the
experiment will be required to complete the postlab
assignment. In some cases your data or representative
student data will be distributed electronically once the
instrument finishes data collection for your section
(which may be about 24 hours after your laboratory
session ends).