From the lab, it's asking to "i.provide the normal mechanism" and I'm a little lost on what that is or what would we try to find within the experiment. Also, what would be the chemical equation from the reaction of the experiment?

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From the lab, it's asking to "i.provide the normal mechanism" and I'm a little lost on what that is or what would we try to find within the experiment. Also, what would be the chemical equation from the reaction of the experiment?   

Diels-Alder Reaction
Introduction:
The Diels-Alder reaction provides a synthesis of six-membered ring compounds. The discovery and development
of this reaction by Otto Diels and Kurt Alder was rewarded with the Nobel Prize in Chemistry in 1950. Today this
reaction is used as a tool to prepare a wide variety of compounds containing six-membered rings, including
natural products and materials of medicinal value.
The Diels-Alder reaction is a concerted [4+2] cycloaddition between a diene and a dienophile (which is often an
alkene). The reaction simultaneously forms two C-C single bonds. The two components required for the Diels-
Alder reaction are a conjugated diene [4 π electrons] and a dienophile [2 π electrons]. The dienophile ("lover of
dienes") must contain at least one it bond, but it may contain more. The mechanism of the reaction involves a
cyclic flow of electrons in a single step (concerted reaction) in which the diene supplies 4 π electrons and the
alkene or alkyne, also called the dienophile, supplies 2 i electrons. In this process, two new sigma bonds which
link the former dienophile to the diene and one new π bond between the former double bonds of the diene are
formed.
diene + dienophile
Even though s-trans conformation of dienes is more stable due to steric reasons, the s-cis conformation is
needed to carry out the Diels-Alder reaction. The s-cis conformation of the diene would yield a six membered
ring with a cis double bond whereas a diene in s-trans conformation would demand a trans double bond in a six
membered ring- an impossible feat. Cyclic dienes, which are locked into the s-cis form, are particularly reactive.
The reaction is stereospecific because the stereochemistry of the reacting components is maintained - trans
substituents on the dienophile are trans in the Diels-Alder product, and cis substituents on the dienophile are cis
in the Diels-Alder product. The Diels-Alder reaction proceeds best if the dienophile contains electron-
withdrawing groups, such as C-O, attached to the bond, and if the diene contains electron-donating groups,
such as alkyl or OR groups.
The reaction you will carry out is between anthracene (the diene) and maleic anhydride (the dienophile):
Anthracene
heat
Maleic Anhydride
Diels Alder Adduct
Transcribed Image Text:Diels-Alder Reaction Introduction: The Diels-Alder reaction provides a synthesis of six-membered ring compounds. The discovery and development of this reaction by Otto Diels and Kurt Alder was rewarded with the Nobel Prize in Chemistry in 1950. Today this reaction is used as a tool to prepare a wide variety of compounds containing six-membered rings, including natural products and materials of medicinal value. The Diels-Alder reaction is a concerted [4+2] cycloaddition between a diene and a dienophile (which is often an alkene). The reaction simultaneously forms two C-C single bonds. The two components required for the Diels- Alder reaction are a conjugated diene [4 π electrons] and a dienophile [2 π electrons]. The dienophile ("lover of dienes") must contain at least one it bond, but it may contain more. The mechanism of the reaction involves a cyclic flow of electrons in a single step (concerted reaction) in which the diene supplies 4 π electrons and the alkene or alkyne, also called the dienophile, supplies 2 i electrons. In this process, two new sigma bonds which link the former dienophile to the diene and one new π bond between the former double bonds of the diene are formed. diene + dienophile Even though s-trans conformation of dienes is more stable due to steric reasons, the s-cis conformation is needed to carry out the Diels-Alder reaction. The s-cis conformation of the diene would yield a six membered ring with a cis double bond whereas a diene in s-trans conformation would demand a trans double bond in a six membered ring- an impossible feat. Cyclic dienes, which are locked into the s-cis form, are particularly reactive. The reaction is stereospecific because the stereochemistry of the reacting components is maintained - trans substituents on the dienophile are trans in the Diels-Alder product, and cis substituents on the dienophile are cis in the Diels-Alder product. The Diels-Alder reaction proceeds best if the dienophile contains electron- withdrawing groups, such as C-O, attached to the bond, and if the diene contains electron-donating groups, such as alkyl or OR groups. The reaction you will carry out is between anthracene (the diene) and maleic anhydride (the dienophile): Anthracene heat Maleic Anhydride Diels Alder Adduct
Reflux Techniques:
In this lab we are using a new technique to carry out our reaction - reflux. When a reaction is heated at reflux,
the reaction is being run at a constant temperature without loss of solvent. The temperature of the reaction is
equal to the boiling point of the solvent (so, in this reaction, we are using xylenes as our solvent for the reaction;
xylenes boil at ~140 °C, thus our reaction is being run at ~140 °C). The reaction is heated until the solvent is
boiling and the condensed vapors are dripping back into the flask from the bottom of the condenser at a steady
rate. Once this is reached, begin the timing for the reflux.
water inc
-Water out
condenser
clamp
round bottom flask
heating mantle
During a reflux it is important that you have water flowing
through your condenser before turning on the heat. Water
should always flow in from the bottom at out of the top.
The water does not need to be on very high - in fact, if you
crank the water up you are likely to pop off your hose and
get water all over the place. You should always have a stir-
bar or boiling chips in your round bottom flask when you
heat it to avoid bumping of the solvent as it heats.
Experimental Procedure
Assemble the glassware for a reflux with a 50 mL round bottom flask. Put a thermometer adaptor at the top of
the water-cooled condenser to prevent excess water vapor from entering the reaction, but still providing a vent
(NEVER heat a completely closed system! This can lead to explosions!). Lightly grease all the joints, and be sure
to use Keck clips to attach the round-bottom flask to the condenser.
Add 1.0 g anthracene, 0.5 g maleic anhydride, 17 mL xylenes, and a magnetic stir-bar to the flask. Make sure to
record the exact amounts of reagents used in your lab notebook! Make sure water is flowing through your
condenser. Heat your reaction to reflux, and reflux the reaction for 25-30 minutes. Remove the hot plate and
allow the flask to cool to room temperature. Then cool in an ice bath. Collect the solid by suction filtration. You
can use a small amount (5 mL) of COLD xylenes to rinse your flask and your crystals.
Dry your product on the vacuum for about 30 minutes; record the weight and melting point range of your
product. Pure 9,10-dihydroanthracene-9, 10-(a,ß-succinic acid anhydride (the product) melts at 261-262 °C.
Transcribed Image Text:Reflux Techniques: In this lab we are using a new technique to carry out our reaction - reflux. When a reaction is heated at reflux, the reaction is being run at a constant temperature without loss of solvent. The temperature of the reaction is equal to the boiling point of the solvent (so, in this reaction, we are using xylenes as our solvent for the reaction; xylenes boil at ~140 °C, thus our reaction is being run at ~140 °C). The reaction is heated until the solvent is boiling and the condensed vapors are dripping back into the flask from the bottom of the condenser at a steady rate. Once this is reached, begin the timing for the reflux. water inc -Water out condenser clamp round bottom flask heating mantle During a reflux it is important that you have water flowing through your condenser before turning on the heat. Water should always flow in from the bottom at out of the top. The water does not need to be on very high - in fact, if you crank the water up you are likely to pop off your hose and get water all over the place. You should always have a stir- bar or boiling chips in your round bottom flask when you heat it to avoid bumping of the solvent as it heats. Experimental Procedure Assemble the glassware for a reflux with a 50 mL round bottom flask. Put a thermometer adaptor at the top of the water-cooled condenser to prevent excess water vapor from entering the reaction, but still providing a vent (NEVER heat a completely closed system! This can lead to explosions!). Lightly grease all the joints, and be sure to use Keck clips to attach the round-bottom flask to the condenser. Add 1.0 g anthracene, 0.5 g maleic anhydride, 17 mL xylenes, and a magnetic stir-bar to the flask. Make sure to record the exact amounts of reagents used in your lab notebook! Make sure water is flowing through your condenser. Heat your reaction to reflux, and reflux the reaction for 25-30 minutes. Remove the hot plate and allow the flask to cool to room temperature. Then cool in an ice bath. Collect the solid by suction filtration. You can use a small amount (5 mL) of COLD xylenes to rinse your flask and your crystals. Dry your product on the vacuum for about 30 minutes; record the weight and melting point range of your product. Pure 9,10-dihydroanthracene-9, 10-(a,ß-succinic acid anhydride (the product) melts at 261-262 °C.
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