Breanna Venable

September 22, 2010

CHEM- 3412: Lab 1

The Diels-Alder Reaction of Anthracene with Maleic Anhydride

Microscale Diels Alder Reaction

Background & Introduction:

The Diels-Alder reaction was discovered by a German professor, Otto Diels, and his graduate student
Kurt Adler in 1928 when they were researching what would occur when electron-poor dienophile
alkenes and alkynes were added to electron-rich dienes. Their experiment showed that two concerted
cycloaddition reactions, cyclohexene and cyclohexadiene, resulted and involved the 4 π-electrons of the
diene and 2 π-electrons of the dienophile. In essence, the reaction entailed the bonding together of the
two carbon – carbon bonds in a single step by cyclic redistribution.

The purpose of this experiment is to use the Diels-Alder reaction in order to form a bridged polycyclic
anhydride by recrystallizing the end product and characterizing it by using its melting point
measurement. Maleic Anhydride will be used as the dienophile and Anthracene will be used as the
diene. Their resulting product is 9,10-dihydroanthraced-9,10-α,β-succinic anhydride, a relatively stable
anhydride that is easily isolated.

Techniques used for this experiment include the use of a reflux condenser involving the heating of a
liquid so that the condensation of its vapors returns to the apparatus. Basically the use of this technique
is to thermally accelerate the reaction by conducting it to its boiling point. Another technique used is
vacuum filtration which is useful to separate solids from fluids by placing a medium through which only
the fluid can pass. Recrystallization was also a technique used in order to purify the compound mixture
of anthracene and maleic anhydride. And finally by taking the melting point of the final product, the
product can be tested for purification.
Procedure: Microscale Diels Alder Reaction

Equipment:
 150 mL beaker Hirsch funnel with adapter
 Boiling chip 2 melting point capillary tubes
 Condenser with tubing microspatula
 5 mL conical vial Pasteur pipet with bulb
 2 Erlenmeyer flask, 10 mL 1 mL pipet
 25 mL filter flask with vacuum tubing
 Sand bath support stand
 Filter paper test tubes
 Glass stirring rod thermometer
 3 mL product vial watch glass
 2 utility clamps ice bath

Experiment Procedure:
1. Reacting Anthracene with Maleic Anhydride
a. Weigh 100mg anthracene and 55 mg maleic anhydride and place in tare 5mL conical vial
b. Add 1.0 mL of Xylene and a boiling chip to conical vial
c. Fit onto condenser
d. Place vial in sandbath to heat mixture at reflux for 30 minutes boiling vigorously
e. Cool mixture at room temperature and then place in ice bath for 5 minutes
f. Add 2 mL of xylene to a test tube and chill in ice bath
g. Collect crystallized solid by vacuum filtration with a Hirsch funnel
h. Rinse crystals with 1mL cold xylene
i. Weigh crude product and set aside a sample for melting point measurement
2. Purifying the Product
a. Place product in 10mL Erlenmeyer flask
b. Add 1-2mL xylene
c. Heat mixture in sand bath until xylene boils
d. Allow solution to cool at room temperature then add to ice bath for 5 minutes
e. Scratch bottom of flask to induce crystallization
f. Collect the crystallized solid by vacuum filtration using Hirsch funnel
g. Rinse crystals with ice cold xylene
h. Spread product on watch glass and allow crystals to dry for 15 minutes
i. Weigh the product and place in a vial
3. Characterizing the Product
a. Measure the melting points for both crude product and recrystallized product

Observations + Data:

When the reaction mixture was in the condenser mixing and boiling, it appeared to be a bright yellow
color that resembles that of urine. When crystallizing some of the crystals were still stuck to the bottom
of the vial and to the Hirsch funnel and filter paper. When recrystallizing the mixture was a lighter shade
of yellow and boiled faster than the first time. The crystals were obtained although many of them still
stuck to the vial when trying to be retrieved. Melting points were taken and compared to see if the
product was pure, and indeed a few impurities were discovered to be present because the melting point
of the product should have been between 260-264 degrees Celsius and the product was actually 263
degrees Celsius.

Discussion + Conclusion:

The reaction boiled and 220°C and when crystallizing had been performed the obtained amount of
crystals was 74.4 mg. Once the experiment was completed and the products tested for melting point, it
was discovered that the melting point was one degree, 263°C from the standard book recorded melting
point,264°C, proving that a bridged polycyclic anhydride can be obtained through the experiment and
thus proves that Diels Alder is a great reaction to accomplish this.