Organic Chemistry Lab

Tuesdays @ 1:30

Lab Experiment 24 Report

Abstract:
In this experiment we compared the relative nucleophilicities of chloride ions and
bromide ions in one of three assigned alcohols. For this experiment I was assigned 1-butanol (nbutyl alcohol). In order to determine the nucleophilicity of the alcohol the two nucleophiles will
be present at the same time in each reaction in equal concentrations. The nucleophiles will be in
competition against one another and the winner will obviously be the more favored nucleophile
and will thus have a bigger presence in the resulting product.. , and they will be competing for
substrate. A protic solvent is used in
these reactions. In general, alcohols do not react readily in simple nucleophilic displacement
reactions. If they are attacked by nucleophiles directly, hydroxide ion, a strong base,
must be displaced. Such a displacement is not energetically favorable and cannot
occur to any reasonable extent:

To avoid this problem, you must carry out nucleophilic displacement reactions on
alcohols in acidic media. In a rapid initial step, the alcohol is protonated; then water, a stable
molecule, is displaced. This displacement is energetically favorable,
and the reaction proceeds in high yield:
Once the alcohol is protonated, it reacts by either the SN
1 or the S
N
2 mechanism,
depending on the structure of the alkyl group of the alcohol. For a brief review of
these mechanisms, consult the chapters on nucleophilic substitution in your lecture

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textbook.
You will analyze the products of the three reactions in this experiment by a
variety of techniques to determine the relative amounts of alkyl chloride and alkyl bromide
formed in each reaction. That is, using equimolar concentrations of chloride ions and bromide
ions reacting with 1-butanol, 2-butanol, and 2-methyl-2-propanol, you will determine which ion
is the better nucleophile. In addition, you
will determine for which of the three substrates (reactions) this difference is important and
whether an S
N
1 or S
N
2 mechanism predominates in each case.

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The purpose of this experiment was to practice purifying and separation techniques. The
techniques we used were thin layer chromatography and column chromatography. In this
experiment we separated and extracted different color pigments from spinach by using different
polar solvents. The extracted pigments were chlorophyll and carotenoid pigments from spinach
leaves using acetone. The pigments were then separated from each other by column
chromatography. In order to extract the desired pigment, solvents of different polarity were used
for both pigments. The resulting collected pigments were then analyzed using thin layer
chromatography.

Results and calculations:

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Discussion:
Our plate showed a nice yellow band for the beta carotene but the chlorophyll in my
opinion could look better. The band for chlorophyll shows not only green but other colors
while the yellow band is nice and of a single color.
Questions:
1. The chlorophylls are more polar than the carotenes. This difference in polarity make the

CH3-CH2-CH2-CH2-OH + H+

2. In a polar protic solvents nucleophilicity tends to go down the periodic table which
results in the following trend: I > Br > Cl > F. This is due to the capacity of hydrogen
bonding. Increased hydrogen bonding adds hindrance to the nucleophile through
solvation.
3. The principal organic by product from this experiment seems to be Isobutylene (2methyl-1-propene). This seems to happen after the
4. Since these compounds are highly volatile, these would evaporate due to being exposed
to the open air. The two halides differ in their rate of decomposition. Having said that, the
two halides would evaporate at a disproportionate rate making the liquid that is left over
richer in the lesser volatile halide. In this instance it seems that the alkyl bromide would
be present in higher quantities.
5. It seems that ammonium chloride is more soluble in alcohol than ammonium bromide so
this could throw off the end product in the experiment.
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6. More of tert-butyl chloride would be made because chlorine is a better nucleophile in

aprotic solvent due to its high electronegativity.
7. Not done.
8. Mole percent because the refractive index of an atom is dependent on the number of
9.

moles of the atom present.

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