Professional Documents
Culture Documents
Experiment 9 Alkenes From Alcohols Analysis of A Mixture by Gas Chromatography
Experiment 9 Alkenes From Alcohols Analysis of A Mixture by Gas Chromatography
reaction plays an important role in this experiment. In an elimination reaction, a halide ion leaves
with another atom or ion (Weldegirma, 2012). Elimination reactions have two mechanisms, E1
and E2. E1 reactions are unimolecular, meaning that the rate of the reaction depends only on the
concentration of the substrate. It has two steps. In the first step, the halogen leaves the molecule,
forming a carbocation. In the second step, the nucleophile extracts a proton from the molecule,
and a pi bond is formed. An E2 reaction is bimolecular, meaning that the rate of reaction depends
on the concentration of the substrate and the nucleophile (Comparing). In this reaction, the
leaving of the halogen, the extraction of the proton, and the formation of a pi bond occur
simultaneously in one step. The products of E1 and E2 reactions are substituted alkenes. Both
mechanisms are favored when there is heat, or a high temperature. Since the competition reaction
of an E1 reaction is the SN1 reaction, heat can favor the elimination reaction over the substitution
reaction. In substitution reactions, the nucleophile replaced a halogen atom in an alkyl halide. In
elimination reactions, the nucleophile acts as a base, meaning that it extracts a proton form the
alkyl halide. E1 reactions are favored when there is a weak nucleophile, such as water, methanol,
ethanol, isopropanol, etc. E2 reactions are favored when there is a strong nucleophile, such as the
Zaitsev's rule, based on the dehydration of alcohols, describes the preference for
eliminations to give the highly substituted (more stable) alkene, which may also be described as
the Zaitsev product (Elimination). As mentioned before, the product of an elimination reaction is
sulfuric acid as a catalyst, to give a mixture of alkenes that can be analyzed by gas
shown in Figure 1., and the possible side reaction during the synthesis of the alkenes is shown in
Figure 2.
OH OH2
i. H
H
ii. H2O
Minor
H
H
H2O
Major
OH
H2O
H
Figure 2. Possible reaction during the synthesis of the alkenes.
Experimental Section
Simple distillation
Oily product
Gas Chromatography
This experiment consists of two parts: the first part is the dehydration of 2-methyl-2-
butanol to form a mixture of alkenes and the second part is the analysis of the alkenes by gas
chromatography. To begin with the first part, 1.50 mL of distilled water were added to a 10.0 mL
conical flask. A total volume od 1.00 mL of concentrated sulfuric acid was added drop wise to
the vial containing the water. The solution was mixed as the sulfuric acid was added. When the
sulfuric acid was added, the solution started to become very hot, so it was placed in an ice bath in
order for it to cool. After the solution was cooled, 2.00 mL of 2-methyl-2-butanol were added to
the vial. The solution was mixed thoroughly, and boiling stones were added to the vial. A simple
distillation apparatus was assembled in order to obtain the mixture of alkenes. The vial
containing the solution was accommodated in the distillation apparatus, a thermometer was
introduced to record the temperature, and the receiving flask was placed in an ice bath to avoid
the vaporization of the distillate. Pellets of calcium chloride were added to the receiving flask in
order to dry the distillate. The sand bath was heated until the temperature reached approximately
30 to 40 degrees Celsius. The solution started to boil and the distillate was collected in a pre-
weighed vial. The vial with the alkene mixture was weighed, and the mass of the alkene mixture
was calculated. The product was then examined by gas chromatography. A clean syringe was
used to take out 1.0 μL of the solution and place it in the injector. A chromatogram containing
Table of Chemicals
Chemicals
Physical Properties 2-methyl-2-butanol 2-methyl-2-butene Sulfuric acid
Molar mass 88.15 g/mol 70.13 g/mol 98.079 g/mol
Melting point -9.0 °C -134 °C 10.0 °C
Vapor pressure 1.60 kPa 2.90 mmHg NA
(20 °C)
Boiling point 101-103 °C 39.0 °C 337 °C
Appearance Colorless liquid Colorless liquid Odorless, clear liquid
Density 805 mg/mL 0.662 g/mL 1.84 g/mL
Table 1. Physical properties of the chemicals used.
Chemicals
Chemical 2-methyl-2-butanol 2-methyl-2-butene Sulfuric acid
Properties
Solubility in water 120 g/dm3 Insoluble Miscible
Flammability Combustible Flammable Highly flammable
Reacts violently with Incompatible with Can react
Reactivity nitric acid, strong bases, strong exothermically with
incompatible with oxidizing agents, bases and diazo
sodium nitrite. alkalies. compounds.
Enthalpy of -380 kJ/mol NA -814 kJ/mol
formation
Table 2. Chemical properties of the chemicals used.
Results
1 𝑚𝑜𝑙 𝑎𝑙𝑘𝑒𝑛𝑒
0.00521 𝑔 alkene × = 0.0000744 𝑚𝑜𝑙 𝑎𝑙𝑘𝑒𝑛𝑒
70.13 𝑔 𝑎𝑙𝑘𝑒𝑛𝑒
Discussion
The gas chromatogram provides the retention time, height, area, and concentration of the
alkenes in the mixture. Based on the chromatogram, it can be observed that there is a major
concentration of one of the alkenes. There is a peak that has more area than the other. The peak
with the highest area belongs to 2-methyl-2-butene, and the peak with the lowest area belongs to
are 12.36 % and 87.6%, respectively. The major product in this mixture is 2-methyl-2-butene.
The high concentration of this compound can help determine which is the major product. The
chromatogram shows that the highest peak corresponds to 2-methyl-2-butene, which means that
2-methyl-2-butene was the most abundant isomer in the mixture. Another reason why 2-methyl-
2-butene is the major product is because it is a more substituted alkene than 2-methyl-1-butene.
The percent yield for the alkenes was very low. During the reaction of 2-methyl-2-butanol
and sulfuric acid, some of the undesired product could have formed, which is the 2-methyl-2-
butanol. This side reaction could have yielded a lower amount of alkenes compared to the
theoretical value. Another possible explanation for the low percent yield might be that some of
the distillate could have evaporated, since the mixture was very volatile. This could have caused
Conclusion
The information of the data has revealed that there was a higher concentration of 2-methyl-
2-butene than 2-methyl-1-butene. This demonstrates the fact that a more substituted alkene is the
and analyzing the mixture by gas chromatography, the relative amounts of the compounds can be
determined. It can also be used to verify which of the compounds in the mixture is the major
product. Side reactions and other factors can affect the overall results of the experiment. The
technique of gas chromatography can be used to analyze mixtures of different types of alkenes.
Different alcohols can be dehydrated to form different alkenes. The lab accomplished what it set
out to do.
References
http://www.masterorganicchemistry.com/2012/10/10/comparing-the-e1-and-e2-reactions/
Elimination Reactions.
http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey04oc/ref/ch05el