Experiment 9
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Classic Diels Alder
Abstract The goal of this experiment was to use a Diels-Alder reaction with anthracene as the diene and maleic anhydride as the dienophile to synthesize 9,10-
dihydroanthracene-9,10-α,β-succinic acid anhydride. Using melting point analysis, thin-layer chromatography (TLC), infrared (IR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy, the final product was examined for purity and identity.
Introduction
In this experiment, anthracene and maleic anhydride were combined to create a
complex compound using the Diels-Alder reaction. It was anticipated that the
reaction would produce 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride.
Procedure
1.
Preheated the equipment to ~180-200 °C.
2.
Assembled a reflux setup.
3.
Weighed 100 mg anthracene and 55 mg maleic anhydride.
4.
Added 1 ml xylene to the vial, attached condenser, and refluxed for 30 min.
5.
Cooled the reaction mixture, transferred to a vial, and cooled in an ice bath.
6.
Vacuum filtered, rinsed with cold xylene, and allowed crystals to dry.
7.
Weighed the product, recorded mass, and determined melting point and IR.
Data
Theoretical amount of 9,10-dihydroanthracene-9,10-
-α,β-succinic acid anhydride: 161mg
Mass of 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride: 96mg
% Yield: 0.096/(0.005x276.3)x100=61.9%
MP of unknown: Heated to 260C and did not melt
Source & Reference:
Handbook of Chemistry and Physics by Chemical Rubber Company
Questions
1.
Draw the mechanism (curly arrows) for the reaction of anthracene with maleic anhydride.
2.
Why is xylene used as the solvent in the reaction instead of benzene or toluene?
It is used as a high-boiling solvent so that the reaction will work fast enough.
3.
Why were we able to use an air-cooled condenser in this reaction instead of a water-cooled condenser?
This is because using water cooled condenser will result in the water reacting again with maleic anhydride or maybe the product. The reverse reaction would also take place. 4.
Why did we need to use a drying tube in the reaction? What might happen if a drying tube wasn’t used?
The drying tube allows moisture to be extracted and contained calcium chloride which has a high affinity for water and can absorb it. Without it we would not be able to obtain a pure product. 5.
On the NMR provided for the product, what protons on the product structure correspond to signals A-C? You do
not need to assign which specific H’s are in each signal.
6. On the NMR for the product, what protons on the product structure correspond
to signal D?
7. On the NMR for the product, what protons on the product structure correspond
to signal E
6.
Why did we need to use a drying tube in the reaction? What might happen if a drying tube wasn’t used?
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164 166
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