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Notes
Chemistry 252
Spring 2006 - Lab.
Laboratory Notebook
Students must maintain a bound (composition style, not loose-leaf or spiral) laboratory notebook, with
pages consecutively numbered. To prepare for the laboratory experiments read the laboratory directions ( in the
laboratory text and supplemental notes) for the entire experiment . Pay special attention to details and cautions
for handling materials!
It is important to prepare your notebook prior to starting any experiment. This helps you better
understand the experiment . Some of the preliminary work on your laboratory notebook should also be done
before coming to the laboratory. This would include preparing a set of notes to follow regarding procedures to
be followed, preparing tables ready to record data etc. You must data and observations in the laboratory (and
NOT on separate pieces of paper for later transfer into your notebook).
Laboratory Safety
You MUST have suitable eye protection at all times in the laboratory, even if you are not doing any
experimental work (others are!). Dispose of chemicals as instructed.
B.
Concise statement of the type of reaction. (e.g. Reduction of a ketone to an alcohol using a
complex hydride reducing agent)
C.
Main Reactions
e.g. C6H5COCOC6H5
+ NaBH4 ~~~~
D.
F.
G.
C6H5CHOHCHOHC6H5
H.
Prepare Table of Physical Constant for Reagents and Products (sample shown below)
Substance
Mol.
Mass
Benzil
210.23 0.50
0.024
NaBH4
37.83
0.10
0.026
Ethanol
46
5.0 mL
mesoHydrobenzoin
214.25
I.
Grams Moles
used
used
Density
Mp
1.074
Bp
solu in
g/100 mL
water
solu in
g/100 mL
ethanol
solu in
g/100 mL
ether
94-95
insol.
sol.
sol.
400dec.
55
4.0
insol.
insol.
sol.
sol.
78.2
137
Calculation:
0.32 g
Percent yield :
= 63%
Comments if any
K.
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THE EXPERIMENTS
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The pages referred to below are those in the NINTH edition of
the Williamson Lab Manual.
I. Borohydride Reduction of a Ketone: Hydrobenzoin from Benzil
Read Chapter 56 of the laboratory text (starts page 532) prior to coming to the laboratory. Follow the
experimental procedure as described on p.503 with the following modifications: 1) Rather than cooling the flask
under a running tap, swirl by hand the flask containing the suspension of benzil in 95% ethanol in a beaker of
ice-water; 2) Filter the cooled solution, after the reaction is done, by gravity prior to crystallization, after
crystallization collect crystals by suction filtration (Hirsch or small Bchner funnel).
Clean-up and disposal: as described in the text , all materials are suitable for disposal in the sink drain, flushed
with water. The product is dried, weighed with yield, observed melting point, and your name on the container
properly labeled is to be turned in to your laboratory instructor for grading.
1) We will use a Bunsen burner flame to crack the cyclopentadiene-dimer in the hood. Add to the
cracking flask 10 mL of mineral oil (chaser!). Your set up will be similar to that shown in Figure 19.1 of the
laboratory manual. However, you will improvise the fractionating column by simply using a reflux condenser
with no water passing through it. Although this is not as efficient as a proper fractionating column, it is adequate
for the task at hand. Make sure that the set-up is assembled with care and all the connections are tight. Make
sure that the monomeric cyclopentadiene is collected in a receiver that is kept ice cold and protected from
atmospheric moisture. The vertical condenser, which act as a fractionating column is not cooled., only the
inclined condenser should be cooled thoroughly by running through it very cold water. Keep the freshly
prepared cyclo-pentadiene cold and well stoppered until you will use it in the Diels Alder Reaction.
2) Keep the excess cyclopentadiene and the residue from the cracking well stoppered until properly
disposed. The dimer and monomer of cyclopentadiene have a very strong unpleasant penetrating odor!
3)For Part 2 heating, use the steam cone. 4) Collect the solid product by suction filtration; 5) Discard all organic
materials (not your product!) in the Organic Waste Container in the hood. Inform you laboratory instructor that
a proper entry be made on the bottle label. The product should be dried, weighed and, placed in a bottle. This
bottle, with a proper label, should be turned in to your laboratory instructor for grading.
aniline. Provide on a separate and also neat sheet of paper the yield, other comments and your name for this part
of the experiment.
of suitable derivatives. You are to prepare derivatives using only those reagents that are available. Some of the
derivatives listed in the laboratory text cannot be prepared because the required reagents are not available. Plan
your work ahead. Reagents are not available for all of the classification tests and derivative preparations as listed
in the laboratory text. Some of the reagents are either particularly hazardous to handle and also risky for the
environment. You should use alternative tests and derivatives, using reagents which are supplied to you in the
laboratory. A list of reagents that are available is given. In addition there are also the reagents you have used in
the course of the semester. Be careful to refer to the lecture text and the laboratory text to ascertain which
reagents are to be used for a particular determination.
Your laboratory instructor will not tell you immediately if you are correct, or not until you actually hand in your
report and the derivatives. If you are incorrect, you will be given some instructions how to proceed.
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