Name

Diels Alder Reaction

Course

Diels Alder Reaction

Objective
The motivation behind this investigation is to frame qn anhydride by method for a Diels Alder
response in the middle of anthracene and maleic anhydride. Anthracene goes about as the diene
and maleic anhydride capacities. Taking after the response, the unrefined item will be
recrystallized. Dissolving purposes of both the rough item and recrystallized item will be brought
and contrasted and the writing esteem. Likewise, an infrared range of the recrystallized item will
be taken. Both softening focuses and the infrared range will be utilized to describe the ite

Reaction Equation

Introduction

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Name

Diels Alder Reaction

Course

In 1950, the physicists Otto Paul Hermann Diels, from Germany, and Kurt Alder, initially
conceived in Prussia and afterward moved to Germany after World War I, got the Nobel Prize in
science for the revelation of another approach to combine cyclic atoms. Suitably titled the DielsAlder Cycloaddition Reaction, this new instrument permitted conjugated dienes to experience
expansion responses with alkenes, yielding substituted cyclohexene items. While there were
various prompt uses for this new response system, business misuses prompted the improvement
of intense bug sprays. These specific mixes more often than not comprised of a carbon ring (or
rings) and numerous chlorine iotas. Chemicals, for example, Aldrin, Dieldrin, Chlordane, and
DDT were all used to secure organic products, vegetables and cotton from soil bugs, termites and
moths. Some had different applications and were utilized to treat parasites like bugs, ticks and
lice.
In this investigation I utilized the Diels-Alder Cycloaddition Reaction instrument to frame
cisNorbornene-5,6-endo-dicarboxylic anhydride from the response of the conjugated diene
Cyclopentadiene with the dienophile Maleic anhydride).. Response to shape cis-Norbornene-5,6endo-dicarboxylic anhydride (Pavia 417). appear to have any handy application, it is a basic
response that serves as a successful sample of this imperative instrument.

Procedure:

0.2g of maleic anhydride was added in test tube of ethyl acetate with 1.0 ml of hexane
0.2 ml of cyclopentadiene was added to the test tube the mixture got warm and it had a

precipitate and the its dissolved. Some bubbles were also seen
The mixture was then cooled in an ice bath and precipitation occurred
A Hirsch funnel vaccum was set and mixture was filtered to get the product
The mass of product is 0.217g
The product was tested using melting point
It started to melt at 110 degree centigrade and completely melted at 166 degree
centigrade

Theoretical Yield
The MW for cyclopentadiene is 66.10 g/mol, and that for maleic anhydride is 98.06 g/mol.
Moles cyclopentadiene = (200 x 10^-3 g)/(66.10 g/mole) = 3.026 x 10^-3 moles
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Name

Diels Alder Reaction

Course

Moles maleic anhydride = (300 x 10^-3 g)/(98.06 g/mole) = 3.123 x 10^-3 moles
Therefore, cyclopentadiene is the limiting reagent.

Observation
A few elements could clarify the moderately yield. In exchanging the adduct from Buchner
channel onto watchglass, some adduct has been stuck on channel paper and is in this manner not
represented in the mass. Be that as it may, channel paper strands also could have been accounted
in the mass amid the same exchange. Some trial blunders additionally add to low yield, for
example, insufficient time was not given for reflux and that channel paper did not cover Buchner
channel complete and some adduct was lost amid washes. Further, butadiene gas could have been
delivered amid reflux because of fast warming, which would not respond with maleic anhydride
and in this manner no adduct would be created. In spite of the fact that the yield is under half,
despite everything it demonstrates that smaller than normal scale reflux was entirely fruitful in
delivering the adduct.
The dissolving point scope of the adduct is taken to be 102-105 C, while the genuine softening
purpose of 4-cyclohexene-cis-1,2 dicarboxylic anhydride is 103-104 C. The refered to
liquefying point falls inside of the scope of exploratory softening point range, which implies that
the virtue of the adduct is entirely high and that reflux was fruitful in instigating the Diels-Alder
response in the middle of sulfolene and maleic anhydride, and that response itself was effective
in creating 4-cyclohexene-cis-1,2 dicarboxylic anhydride in high immaculate

Characterization
In a Diels-Alder reaction, all the atoms remain with the molecule, so the MW would be 66.10 +
98.06 = 164.16 g/mole.
100% conversion would yield 3.026 x 10^-3 moles, so grams would be (3.026 x 10^-3
gm)*(164.16 g/mole) = 0.4967 g, or 497 mg
Yield = 375 mg/497 mg x 100% = 75.5%

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Name

Diels Alder Reaction

Course

Conclusion
The purpose of this reaction was achieved. The evidence from the qualitative testing performed
in the laboratory confirms the formation of six-membered rings by cycloaddition, also known as
a Diels-Alder reaction. The melting point analysis shows that the product of the Diels-Alder
reaction was somewhat impure, but the product of the hydrolysis of the Diels-Alder adduct was
very pure. The yield of the reactions was also high; 89% and 75% for the two processes
respectively. Although the specific structural details of the products of the reaction were not
viewed directly, the qualitative tests showed the reactants were very different than the products.
The decomposition of 3-sulfolene proved to produce the cis- isomer of 1,3-butadiene. If it had
produced a mixture of cis- and trans- forms, then the yield of the cycloaddition would have been
much lower than 89%. The product of the reaction was confirmed to contain at least one double
bond by the positive reaction to the bromine and Baeyer tests. The melting point test showed that
the product was impure, however. The impurity could have come from the drying process.
During drying, the anhydride was exposed to the air. Moisture from the air could have reacted
with the highly hydrophilic anhydride, converting it to the dicarboxylic acid form of the
molecule. However, the dicarboxylic acid has a much higher melting point than the anhydride, so
this unknown impurity in the first product must have a lower melting point than 1000C. The
other possibility could be the unreacted 3-sulfolene or maleic anhydride, which have a lower
melting point than the anhydride product.

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