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1. In the space below, give your risk assessment from Experiment 5 (Purification
of Cholesterol) by noting
the H and P codes for all chemicals and reagents used, and explaining the
meanings of those H and P
codes.
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solution (NaCl) disclosed according to the
Volume: 20 cm3 applicable regulations.
Anhydrous magnesium No components need to be
sulphate (MgSO4) disclosed according to the
For collecting and dry the applicable regulations.
organic layer
2.
(i) Attach your IR spectra for cholesterol and dibromocholesterol to this report.
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IR spectrum for Dibromocholesterol (this IR spectrum was taken
from Georgia)
(ii) In the tables below highlight the significant IR peaks for each
compound, and assign each peak to a specific functional group.
*TIP*: If any peaks involved in the key functional group (FG) transformation prove hard
to spot, you should make a note of this, and estimate the peak position instead.
Dibromocholesterol Cholesterol
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(ii) Give a brief discussion of how the information gained from IR spectroscopy
can be used in conjunction with other methods to confirm the structure
of a compound.
3. Choose one of the experiments that you carried out (Experiments 5-7) and give
a brief write-up of the
experimental method that you followed. This should include enough information
to allow another
person to repeat this work, and should be written in the third person and past
tense (i.e. not I did this,
and I did that but rather the reagent was added to the solvent).
*TIP*: This is not an exercise in simply reproducing a verbatim copy of the procedure already
provided.
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containing a mixture of 10 cm3 ice-water and 1 cm3 concentration hydrochloric acid. After a
few minutes the precipitated product was collected by suction filtration using a Buchner
apparatus, and was washed with 2 portions of 5 cm 3 portions of water. The crude product
was dried by suction at the filter pump for 10 min., and then was recrystallised from
petroleum ether.
The yield and melting point of the pure product were recorded. IR spectra of the product
was recorded and of the benzophenone starting material for comparison. The IR spectra
was Interpreted, any significant changes were noted between starting material and product.
The IR spectrum of the product should be kept to help you with the report. The purity of the
product was checked by TLC. Dilute samples of the obtained product was spotted and the
starting material (benzophenone) onto a TLC plate and elute using a 9:1 mixture of
petroleum ether and ethyl acetate. The developed plate was visualised under UV light,
then, the spots was circled using a pencil, and the R f value of the two compounds were
worked out. A picture of an annotated TLC plate was taken.
4.
(i) Provide an original drawing for the full reaction mechanism for the
nitration of benzene.
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(ii) Show your calculation for working out the percentage yield of the final
product.
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5-Nitrosalysilic acid
Salicylic acid
M.wt 138 gmol-1 183 gmol-1
From the 1 mol 1 mol
equation
1.38 g
138 g X
mol
0.01 mol X
Number of 0.01 mol of 5-Nitrosalysilic X183.118 gmol-1 = 1.83g
mol (Theoretically)
5-
Nitrosalysilic Actual yield = 0.91g
acid (X) =
Percentage Actual yield 0.91 g
= x 100 = 49.73%
yield Theoretical yield 1.83 g
The maximum theoretical mass of product in a certain reaction is 1.83g, but only 0.91g is
actually obtained. The low percentage of yield obtained might be due to several reasons such
as: some product may be lost when it is removed from the reaction mixture or some of the
reactants may react in an unexpected way.
When we have two functional groups on benzene ring such as CO 2H and OH as salicylic
acid compound, the orientation of electrophile ( NO 2+) will be directed to 5-position of
salicylic acid because of the OH is strongly activating group ( Ortho-Para director) while
CO2H is moderately deactivating group (Meta-director). Therefore, the major product is 5-
nitrosalicylic acid. As illustrated in next equation:
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Major product
minor product
5.
(i) Either sketch or insert a picture of the TLC for this reaction, including
as much detail as possible. Fully explain the relative positions of the
spots for the starting material and product.
Diphenymethanol (alcohol product) has higher polarity than the ketone such as
benzophenone (starting material). In fact, polar compounds such as alcohol stick to the
adsorbent/ being interacted with (the stationary phase) more readily, and thus do not elute
as far and have a lower value for Rf compared with compounds with less polarity such as
ketones; therefore a higher value of Rf because of the faster elution. Moreover, TLC plate is
a given set of conditions where the Rf values of two spots on it may provide some
indications or an evidence as the identity of a compound, and the success or even failure of
a reaction. In terms of TLC being used as an indicator for purity, usually a pure compound
when spotted and developed on a TLC plate appears as a single spot, while two or more
spots in a single (lane) might indicate that the compound is impure.
(ii) Report the melting point of your diphenylmethanol product and show
how you were able to use this as an indicator of purity.
m.p. = 66oC
m.p. = 65-67 C (Literature) (Sigma Aldrich)
Clearly, diphenylmethanol which is formed in the experiment is highly pure solid. Since
the presence of a small amount of impurity substances will lower a compounds melting
point by a few degrees and widen the melting point temperature range. Defects in the
crystalline lattice results from impurity substances, it is easier to overcome the
intermolecular interactions between the molecules.
The desired compound (diphenylmethanol) is a very pure organic crystal. Pure compounds
have all of the molecules the same; they are arranged and packed together in a very
orderly array. In this array, the attractive forces between the molecules are maximized. All
of the molecules are identical, and adhere tightly together in an orderly, three-dimensional
array. Thus, the structure is strong, and it is not easily can be overcome by an input of
energy. On the other hand, impure compounds require a lower temperature in order to be
melted than is required to melt the pure structure where no impurities present. Moreover,
impure solids melts over a wider temperature range due to regions within the crystal that
contain different amounts of the impurity, and therefore different numbers of distorts in the
crystalline molecules wall occur.
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By using Grignard reagent As following :
6. Briefly explain how you could use IR spectroscopy to differentiate between the
following groups of
compounds. For each compound predict where you would expect the main peaks
in the IR spectrum of
that compound to appear (in the range 500-4000 cm-1).
Compou
nd
Mean
peak C=O : 1740- C=O : 1750- C=O :1670- NH : 3500- S=O : 1050
v cm-1 1720 1730 1640 3100
In compound # 1 the C=O band appears between 1740-1720 cm-1 and the intensity is
strong
In compound # 2 the C=O band appears between 1750-1730 cm -1 and the intensity is
strong
In compound # 3 the C=O band appears between 1670-1640 cm-1 and the intensity is
strong
In compound # 4 the NH band appears between 3500-3100 cm-1 and the intensity is
moderate
In compound # 5 the S=O band appears near 1050 cm-1 and the intensity is strong.
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Skills Competency Grid
Fill out the following grid giving brief reflections on where you acquired
the following skills during Section 2 (Synthetic Organic Chemistry,
Experiments 5-7) of the laboratory course:
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crystal lattice. This results in the increase in
the purity of the desired product.
Determination of a melting point, and (Experiments (5,6 & 7). During these
implications for assessing product purity. experiments, the melting points have been
determinated and this technique increases
the ability to indicate to the purity of the
desired products. Moreover, the filter paper
used to filtrate the product obtained from
the impurities.
Analytical tests for product purity. In Experiments (5,6 &7). The spectrum
technique was used. the observation made
was when The desired constituent has Rf~
0.7cm. IT has been observed that when Rf is
too low, then the solvent system is too non-
polar. As a result, it will take very long time
for the material to come up to the column.
Alternatively, if f is too high, then the
solvent system is too polar and the material
will come up to the column too quickly with
pore separation.
Understanding of the Percentage Yield In Experiments (5,6 &7). This represents the
of a reaction. actual recovery amount obtained. The
formula of Percentage Yield (Actual amount
Theoretical amount) X100
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