Experiment 5ab

Experiment 5AB: Multi-step Synthesis & Esterification
Gabby Vogel
SCH 211-04
Dr. Bartelson
2
Abstract:
A mixture containing maleic anhydride, ethyl acetate, hexane, and dry cyclopentadiene was
synthesized to create “cis-norborene-5,6-endo-anhydride” was synthesized from the reactions
above by a Diels-Alder reaction. The synthesis of the product from previously stated was a
hydration of the solution. Approximately 2.26 grams of crystals were collected from the first
synthesis. Approximately 1.46 grams of crystals were collected from the second synthesis. The
synthesis took place in three parts. The first part an anhydride was synthesized from maleic acid
and cyclopentadiene by a Diels-Alder reaction. The second part an endo-diacid was synthesized
from the endo-anhydride by a hydration reaction. Lastly, the third part an endo-diester, the end
product, was synthesized from an endo-diacid and menthol by Fischer Esterification. A melting
point analysis, IR spectroscopy, and a H1NMR were used to analyze the products.
Figure 1. The chemical reaction of cyclopentadiene and maleic anhydride to create the endo
anhydride
Figure 2. The chemical reaction of the endo anhydride created undergoing hydration to create an
endo-diacid
3
A Fischer esterification, the refluxing of carboxylic acid and an alcohol in the presence of a
strong acid catalyst, took place in this step. Concentrated sulfuric acid was added into the endo-
diacid as well as methanol and refluxed. Then various extractions were done to purify the
compound. This allowed for a clear and viscous liquid to be collected. Approximately 59% of
the ester was collected.
Figure 3. The chemical reaction of an endo-diacid and methanol to create an endo-diester
Experimental 5A:
To create an endo- anhydride, maleic anhydride (2 g, 0.02 mol) and ethyl acetate (6 mL)
were added to a 50-mL Erlenmeyer flask. The solution was then heated on a hot plate. Hexane (6
4
mL) was added after the solution was taken off the hot plate and then left to cool to room
temperature. When room temperature was achieved, dry cyclopentadiene (2 mL) was added to
the cold anhydride solution. Forming a solid white precipitate. The cooled to room temperature
solid was refluxed using the hot plate and then left undisturbed to allow crystal formation.
Suction filtration occurred for approximately 5 minutes and small amounts of cold hexane was
used to obtain the crystals. The endo-anhydride product was then weighed and set aside.
To synthesize an endo-diacid, endo-anhydride (2.26 g, 0.012 mol) and distilled water (50
mL) were added to a 125-mL Erlenmeyer flask. The contents were heated to reflux, the solid
compound melted. The solution was left to cool, undisturbed, for 30 minutes. After the time is
up, a stirring rod was used to poke the solution until crystal formation occured. A suction
filtration was performed using small amounts of cold water to wash the crystals.
Endo-diacid (3 g, 0.02 mol) was added to a 25-mL round bottom flask using a powder
funnel. Methanol (12mL), sulfuric acid (0.60 mL), were added to the round bottom flask and
dissolves. The mixture was then refluxed for an hour using a prepared hot water bath. The
reaction was cooled to room temperature and then put in an ice bath. The contents were then
transferred to a separatory funnel with water (15 mL). Three extractions were performed using t-
butyl methyl ether (15 mL), saturated aqueous sodium bicarbonate (15 mL), and aqueous sodium
chloride. The organic mixture was then poured into an Erlenmeyer flask and anhydrous
pelletized calcium chloride (0.5 g) was added to the flask and swirled. Solution was decanted
into a 50-mL Erlenmeyer flask. The solution was then rotary evaporated leaving behind a clear,
colorless, and viscous liquid.

5
Results and Discussion:
This experiment yielded 3 different products; an endo-anhydride, endo-diacid, and an
endo-diester. The endo-anhydride was formed by a Diels-Alder reaction, the endo-diacid was
synthesized by a hydration reaction, and the endo-diester was synthesized by a Fischer
esterification. The endo-anhydride yielded 2.26 grams of product. The endo-diacid yielded 1.4
grams of product. The melting point range of the endo-anhydride `was 160.2°C - 167°C. The
actual melting point range is between 165°C - 167°C. This indicates that the compound that was
produced from the experiment has similar characteristics but shows some impurity based on it
starting to melt 5°C below the actual range. The melting point range of the endo-diacid was
172°C - 179°C. The actual melting point is 175°C. This again indicates that there are similar
characteristics of the compounds but there could be some impurities. The first reaction had
a113.5% yield, the second had a 64.9% yield, and lastly the third one had a 59.0% yield.
Endo-anhydride:
6
Endo-diacid:
Endo-diester:
Table 1. Melting Point Ranges

Compound: Melting Point Range (°C): Actual Melting Point (°C):
Endo-Anhydride 160.2 - 167 165 – 167
Endo-Diacid 172 - 179 175
Table 2. Endo-Anhydride Reaction Table

Maleic Anhydride Cyclopentadiene Endo-Anhydride
Molecular Weight 98.06 66.1 164.16
(g/mol)
Density (g/cm3) N/A 0.805 N/A
Amount 2g 2 mL 2.26 g
mmol 2.04 x 10-5 2.44 x 10-5 1.38 x 10-5
Percent Yield: 2.26/1.99 x 100% = 113.5%
Theoretical Yield: 1.99 grams
Table 3. Endo-Diacid Reaction Table

Endo-Anhydride Water Endo-Diacid
Molecular Weight 182.17 18.02 182.17
(g/mol)
Density (g/cm3) N/A 1 N/A
Amount 2.26 g 27 mL 1.4 g
mmol 1.24 x 10-5 1.50 x 10-3 7.69 x 10-6
Percent Yield: 1.46/ 2.25 x 100 = 64.9%
7
Table 4. Endo-Diester Reaction Table

Endo-Diacid Methanol Endo-Diester Water
Molecular Weight 182.17 32.04 182.17 18.02
(g/mol)
Density (g/cm3) N/A 1 N/A 1
Amount 1g 27 mL 1.4 g 5 mL
mmol 5.49 9.88 x 10-5 7.68 2.77 x 10-4
Percent Yield: 0.59/1.00 x 100 = 59%
IR Spectroscopy of the endo-diacid

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H1NMR of the endo-diester
IR Spectroscopy of endo-anhydride
9
IR of endo-diester

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Experiment 5AB: Multi-step Synthesis & Esterification

synthesized to create “cis-norborene-5,6-endo-anhydride” was synthesized from the reactions

the ester was collected.

Figure 3. The chemical reaction of an endo-diacid and methanol to create an endo-diester

colorless, and viscous liquid.

Results and Discussion:

This experiment yielded 3 different products; an endo-anhydride, endo-diacid, and an

synthesized by a hydration reaction, and the endo-diester was synthesized by a Fischer

Table 1. Melting Point Ranges

Table 2. Endo-Anhydride Reaction Table

Table 3. Endo-Diacid Reaction Table

Theoretical Yield: 2.25 grams

Table 4. Endo-Diester Reaction Table

IR Spectroscopy of the endo-diacid

H1NMR of the endo-diester

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