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Diels Alder lab

Diels Alder lab

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Published by peejes
Furan rxn with Maleic anhydride
Furan rxn with Maleic anhydride

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Published by: peejes on May 24, 2012
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04/15/2013

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Diels-Alder ReactionFuran and Maleic Anhydride
 
Introduction:
 The objective of the experiment is to perform the Diels-Alder[4+2] cycloaddition of Furan and Maleic Anhydride and use NMRspectroscopy to determine the product formed. This type of reaction hasthe possibility of forming both endo or exo furan-maleic anhydrideadducts.
Theory:
 The Diels-alder reaction occurs when a conjugated diene and anisolated alkene are added together in one step. The bonding electronsredistribute forming two carbon-carbon bonds to create a cyclic product.With a cyclic diene and cyclic dienophile, two products form that havedifferent stereochemistries. They are the exo and endo-adducts. The endo-adduct is the kinetic product as it is faster and takes lessenergy to form. It is less stable than the exo-adduct, which is thethermodynamic product, so the endo is easily reversible in equilibriumconditions. When equilibration occurs, the fast reversal of the endoallows for gradual build up of the exo so that the exo will be the majorproduct.Furan (C
4
H
4
O), the diene of the reaction, is a five-memberedconjugated ring. It reacts with maleic anhydride (C
4
H
2
O
3
), the dienophileof the reaction, which has a five-membered ring with an isolated pibond. The possible products formed are the endo and exo furan-maleicanhydride adducts (C
8
H
6
O
4
).  The experiment can be carried out under specific conditions inorder to contol what the major product will be. If the reaction is donequickly, isolating the endo, it will be the major product. If the reaction isdone over a longer period of time, exo will be the major product.
 
Materials:
Maleic anhydride, furan, ethyl acetate, acetone, hexane,dueterated chloroform or acetone-d
6
, pipet, vials, graduated cylindar,NMR tube, cotton, glass pipet, test tube
Procedure:
Day 1:Dissolve 400mg maleic anhydride with 2ml ethylacetate in a vial. Add 0.4ml furan. Seal vial and place in refrigerator untilnext lab so that it crystallizes.Day2: Pipette out excess liquid from the crystals. Dissolve thecrystals in a minimal amount of acetone. Add just enough hexane for thesolution to get cloudy.Let it recrystallize for next lab.Day 3: Pipette out any solvent left in vial wih crystals then leavevial open in drawer.Day 4: After crystals have dried, prepare for NMR.Dissolve crystals in a minimal amount of soplvent and filter 1ml throughcotton in glass pipet into the NMR tube.HNMR spectroscopy.
Hazards/MSDS:
Discussion:
We ran into many obstacles when trying to carry out thisexperiment and we needed to repeat it. The first time we performed theexperiment, the crystals did not recrystallize for day three. Weeventually got crystals and when we completed the experiment andviewed the HNMR spectrum, only acetone was visible.Errors could have been made in adding too much solvent, the wrongsolvent or even in the preparation for NMR.We repeated the experiment and it went much better than thefirst time. We made sure to use minimal amounts of each solvent as wethought that may have been our original error. The HNMR spectrumshowed the major product we expected. There were additional peaks forunreacted starting material in addition to the peaks indicating thesolvents.

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