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001
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).
Ph
Br
Ph =
Ph
H
meso-stilbene dibromide
?
Br
Ph
Ph
(E)-(1-bromoethene-1,2-diyl)dibenzene
Ph
Ph
1,2-diphenylethyne
v.001
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