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20200708011217exp 4 3 Diels Alder Reaction Report Template 1

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Subject
Chemistry
School
University of Nevada Las Vegas
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Homework
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Name:
CHEM XXXX
Section #: XXXX
DIELS-ALDER REACTION
Purpose: To perform the experiment of Diels-Alder reaction between 1, 3-butadiene and
maleic anhydride to measure the percentage yield of the product cis-4-cyclohexene-1, 2-
dicarboxylic anhydride.
Procedure:
Formation of Product: 0.098 g of maleic anhydride and 0.260 g of 3-sulfolene were
placed in a 3 mL conical vial with a boiling chip. Then, 15 drops of xylene were added to
the mixture as reagent. Thereafter, the conical vial was placed on a hotplate with an
aluminum block for the reaction purpose. A condenser was connected to the tap water
and a thermometer was also placed on the hotplate through the hole of the aluminum
block. After that, the tap water was turned on and the outlet water hose was placed in the
sink. The mixture was heated until it boiled and this process was continued for 20 minutes
more (this process is known as “reflux”). Then, the mixture was cooled down after the
reflux. The solution from the conical vial was transferred to a Craig tube. Finally, 10-20
drops of toluene was added to the solution.
Recrystallization: The Craig tube was placed in hot water bath until all solids were
dissolved. Then the Craig tube was cooled down slowly. To speed up the process of
crystallization, hexane to the Craig tube was added dropwise and the solution was stirred
until precipitate was formed. After that, the precipitate was dissolved in hot water bath.
The mixture was cooled down slowly. After repeating this process several times, all the
crystals were collected on a pre-weighed watch glass. The crystals were dried for 10
minutes. The actual and theoretical yields were calculated followed by the percentage
yield. Finally, the melting point of the product was observed carefully and noted down.
Data/Results:
Reagents
Required # of mmol
Actual mass used
(g)
Actual # of mmol
Maleic anhydride
1.0
0.0994
1.014

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3-sulfolene
2.2
0.2629
2.225
The mass of the pre-weighed watch glass = 56.2129 g
The mass of the watch glass + the product = 56.2516 g
The actual yield of the product = 0.0387 g
The limiting reagent = Maleic anhydride
The theoretical yield = 0.15428 g
S
O
O
140
o
C
xylene
+
SO
2
(g)
3-sulfolene
1,3-butadiene
(diene)
O
O
O
140
o
C
xylene
O
O
O
maleic
anhydride
(dienophile)
cis-4-cyclohexene-1,2-dicarboxylic
anhydride
1,3-butadiene
(diene)
So, 1 mol of 1, 3-butadiene reacts with 1 mol of maleic anhydride. We have actual
amount of each reactants. We see there is excess mmol of 3-sulfolene which
corresponds to equal mmol of 1, 3-butadiene. So, limiting reagent is maleic anhydride.
From the reaction we see, there is equal mmol of product will form compared to each
mmol of maleic anhydride. So, theoretical yield is 1.014 mmol.
Mass of product = 1.014 × 10
−3
× 152.149 𝑔 = 𝟎. 𝟏𝟓𝟒𝟐𝟖 𝒈(𝑻𝒉𝒆𝒐𝒓𝒆𝒕𝒊𝒄𝒂𝒍 𝒚𝒊𝒆𝒍𝒅)
The percent yield =
𝑨𝒄𝒕𝒖𝒂𝒍 𝒚𝒊𝒆𝒍𝒅
𝑻𝒉𝒆𝒐𝒓𝒆𝒕𝒊𝒄𝒂𝒍 𝒀𝒊𝒆𝒍𝒅
× 𝟏𝟎𝟎 = 𝟐𝟓. 𝟎𝟖 %
Experimental melting point of the product = 135 ˚C
(Cis-4-cyclohexene-1, 2-dicarboxylic anhydride, lit. M.P. = 102 ˚C)

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Name: CHEM XXXX Section #: XXXX DIELS-ALDER REACTION Purpose: To perform the experiment of Diels-Alder reaction between 1, 3-butadiene and maleic anhydride to measure the percentage yield of the product cis-4-cyclohexene-1, 2dicarboxylic anhydride. Procedure: Formation of Product: 0.098 g of maleic anhydride and 0.260 g of 3-sulfolene were placed in a 3 mL conical vial with a boiling chip. Then, 15 drops of xylene were added to the mixture as reagent. Thereafter, the conical vial was placed on a hotplate with an aluminum block for the reaction purpose. A condenser was connected to the tap water and a thermometer was also placed on the hotplate through the hole of the aluminum block. After that, the tap water was turned on and the outlet water hose was placed in the sink. The mixture was heated until it boiled and this process was continued for 20 minutes more (this process is known as ...
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