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Running head: DIELS-ALDER REACTION
Diels- Alder Reaction: Synthesis of 9,10 – dihydroanthroceno-9,10-edo-
α, β-succinic
anhydride
Anjenelle Fernandez, Steve Smith
University of South Florida
CHM 2211L: Organic Chemistry II Lab
DIELS-ALDER REACTION
2
Synthesis of a Biodiesel and a Soap
Esterification is the term that refers to the process of forming an ester (Clark, 2023). A specific form of esterification is transesterification which refers to the process of obtaining a carboxylic acid ester specifically from a different carboxylic acid ester (Farmer & Gunawardena,
2023). A common way that this occurs is through the utilization of an acid catalyst during a reaction between an ester and an alcohol. Saponification is the formation of soap which occurs through a reaction in which an ester in a water and a base forms a carboxylic acid and an alcohol (Farmer, 2023). However, due to the presence of the strong base, a carboxylic ion is formed in place of the carboxylic acid. An example of transesterification is the formation of biodiesels from triglycerides, for example an animal fat. This occurs the presence of an acid and uses an excess of the alcohol to drive the reaction in the forward direction. One example of saponification is the formation of soap from coconut oil. This reaction occurs in basic conditions and is irreversible.
DIELS-ALDER REACTION
3
Figure 1: Detailed mechanism for the preparation of biodiesel
Figure 2: Mechanism for preparation of soap
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+allow to separate for 20-30 minutes
+ see 2 layers
DIELS-ALDER REACTION
4
Figure 3: Potential unwanted side reaction for preparation of biodiesel Figure 4: Potential unwanted side reaction for preparation of soap
Experiment
Procedures
Part A: Preparation of a Biodiesel
]
Conical Flask (250 mL)
+ Stir bar
+ 300 mg KOH
+ 8.5 mL methanol
+ cover flask with parafilm
+ stir until dissolved
+ “heated” 32 mL vegetable oil
+ cover with parafilm
+ stir at 60
°
C for one hour
Separatory Funnel
Bottom layer
(glycerol)
Top layer
(biodiesel)
DIELS-ALDER REACTION
5
Biodiesel
Part B: Preparation of a Soap
Chemicals
Top layer
(biodiesel)
+ take 3 mL of biodiesel
+ do 27/3 MeOH test
+ pipet out 3mL top layer
+ pour into measuring cylinder with 27 mL of MeOH
+ mix
+ if homogeneous then positive
+ once identity is confirmed
+ drain the remaining layer
+ weigh
+ calculate % yield Confirms biodiesel
250 mL Beaker
+ large stir bar
+ 50 g coconut oil
+ heat at 100°C
+ 30% NaOH solution
Basic Solution
+heat and stir at 90-100°C for one hour until too viscous to stir
+ transfer molten soap to watch glass let cool
+ shape and compress the semi-solid soap into a bar
+compare cooling soap and let dry for two weeks
+ coconut soap must be superfatted with coconut oil to avid over drying of skin
Graduated Cylinder
+add small piece of soap
+ 5mL of water, shake
+foaming?
+ test pH with litmus paper
+ CaCl
2
to dry water
+ foaming diminished?
Triacyclglycerol Triaglyceride
DIELS-ALDER REACTION
6
Results
Glycerol
Formula: C
3
H
8
O
3
Molar mass: 92.09 g/mol
Melting point: 18 °C
Boiling point: 290 °C
IUPAC: propane-1,2,3-triol
Hazards:
Flammable
Can irritate skin and eyes
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DIELS-ALDER REACTION
7
Mass of biodiesel: Color: clear with slight yellow tint
Appearance: thick liquid
Mass of Soap: 69.2
Odor: coconut
Appearance: white, solid, opaque
Discussion
The overall reaction to prepare tge biodiesel accomplished the original goal and from the green chemistry perspective it is an efficient and low cost way to form a biodiesel in a way that is good for then environment in that it does not produce any harmful biproducts and is from a renewable source, a vegetable fat. In the preparation of soap, this reaction is important because it
efficiently forms a soap with no harmful biproduct and produces little waste. This is important as
it allows for the formation of soaps and biodiesels in large volumes in a way that is good for the environment and can replaces other methods that are harmful to the environment. Conclusion
In conclusion, the data collected by the experiment does connect to theory as the aim of synthesizing the biodiesel and soap was accomplished. The data reveals that one can form a soap
and a biodiesel from a vegetable or animal fat. The techniques of this experiment can be applied to form other biodiesels from different forms of animal or vegetable fats than those used in this experiment.
DIELS-ALDER REACTION
8
References
Clark, J. (2023, January 23). Making esters from alcohols
. Chemistry LibreTexts. Retrieved April 20, 2023, from https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Org
anic_Chemistry)/Esters/Synthesis_of_Esters/Making_Esters_From_Alcohols Farmer, S. (2023, January 23). Saponification
. Chemistry LibreTexts. Retrieved April 20, 2023, from https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Org
anic_Chemistry)/Esters/Reactivity_of_Esters/Saponification Farmer, S., & Gunawardena, G. (2023, January 23). Transesterification
. Chemistry LibreTexts. Retrieved April 20, 2023, from https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Org
anic_Chemistry)/Esters/Reactivity_of_Esters/Transesterification Weldegirma,S. (2023).
Experimental organic chemistry laboratory manual: CHM 22110L and CHM2211L
. University of South Florida.
Related Questions
The Diels-Alder reaction is not limited to making six-membered rings with only carbon atoms. Predict the products of the following reaction that produce rings with atoms other than carbon in them.
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Draw the structure of the product of the Diels-Alder reaction below.
H3C
CH3
O
||
O
||
+ CH3OC-CEC-COCH3
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70 ins210 V16225050
panx qalborgo
3) In a recently-published synthesis of yohimbine (used in folk medicine as an aphrodisiac), the
Diels-Alder reaction was used to form a new ring during a key step.
R
OtBu
Diels-Alder
a. Draw a circle around the four atoms of the diene group in this molecule.
b. Draw a square around the two atoms of the best dienophile group in this molecule.
c. Draw the product of this reaction, ignoring stereochemistry.
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•
--
H
(b)
H,C
3-methylhexane
CH,
(c)
B
கூ
CH, CH,
HgCG;
சீகூ
H₂CH H
3-ethyl-1-methyloctane
3,3 diethyl pentane
5Å, Å,CH,
W
CH3
CH2
CH₂
W21 Su2...
CH3
X
-CH3
G
b
F
E
L
c
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4
COOH
OCH₂
OCH₂
CH₂
CN
&
CN
CH₂
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4B1
Write the possible reactants that gave the following products in
the Diels-Alder reaction
oso
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4B2
Write the possible reactants that gave the following products in
the Diels-Alder reaction
-H
O OEt
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Please help answer
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Need help with this question. Thank you :)
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For our Diels-Alder Reaction lab, they asked to provide heat to the structures and I'm a little unsure of what the products will look like, if you can help, please?
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How do we carry out a Diels-Adler reaction in the bottom problem?
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GO3
ce
Br
- HzO
58) , &o4
NH2 (CHz),
4
- H20
59 HOCCHZ) 4
애
6) HoE (CH), čoH
ex ces
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Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants,
in one step, by moderately heating the reactants?
O
• If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in
any arrangement you like.
2
dla
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The boiling point of methylcyclohexane (C7H14, MW 98.2) is 101°C. The boiling point of perfluoromethylcyclohexane (C7F14, MW 350) is 76°C. Account for the fact that although the molecular weight of perfluoromethylcyclohexane is over three times that of methylcyclohexane, its boiling point is lower than that of methylcyclohexane.
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Chemistry
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Please provide Y and Z
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do all part with 30 min plz with clear handwriting in white Page
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Conjugated Pi Systems
Predicting the products of simple Diels-Alder reactions
Predict the major products of the following organic reaction:
+
་
Δ
?
Some important notes:
•
Draw the major product, or products, of the reaction in the drawing area below.
• If there aren't any products, because no reaction will take place, check the box below the drawing area instead.
• Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers.
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