Analysis of the Products of a Diels Alder Reaction between EEhexa24dien1ol and Maleic Anhydride

Analysis of the Products of a Diels Alder Reaction between EEhexa24dien1ol and Maleic Anhydride

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Lab 3: Analysis of the Products of a Diels- Alder Reaction between E,E -hexa-2,4- dien-1-ol and Maleic Anhydride Performed: 02/21;23;28/2012 Manuel Vazquez
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INTRODUCTION: This experiment was designed and performed with the intention of determining the products formed from the Diels-Alder reaction of E,E -hexa-2,4-dien-1-ol, a diene, and maleic anhydride, a dienophile. The product was first to be hypothesized by the known reaction mechanism, and then the true product was to be determined via spectroscopic analysis using an IR spectrum, a 13 C NMR, and both a 1D and 2D COSY 1 H NMR. The Diels-Alder reaction involves two main compounds: a diene, and a dienophile. In solution, under reaction conditions, the pi electrons of the dienophile attack the pi system of the diene, resulting in a ring-like exchange of electrons which forms a final ring product with a single double-bond between the two inner carbons of the diene (Figure 1). Distinct factors, such as whether or not the diene and dienophile’s subsitiuents are cis or trans in relationship to their own structures, in turn result in the relative stereochemistry of those substituents in the ring structure; specifically, if the substituents on the diene are both cis, or both trans, then they will end up on the same face of the final ring, and if they differ from one another (i.e. one of the double-bonds has a cis substituent, and the other one has a trans substituent) then the two substituents in question will be on opposite sides of the final ring the same applies to the dienophile, with a cis-configuration ending in equiplanar substituents, and with a trans configuration ending in the substituents being on opposite faces of the ring. Figure 1: A generic Diels-Alder Mechanism Figure 2a: The Diene Figure 2b: The Dienophile Figure 2c: The Predicted Product Commented [P1]: Figure 1: The Diels-Alder Reaction Mechanism
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Here, the diene E,E -hexa-2,4-dien-1-ol (Figure 2a) has both the methyl substituent on the 4 th carbon and the -CH 2 OH substituent on the 2 nd carbon in the trans position in relation to their respective double-bonds, and the dienophile maleic anhydride (Figure 2b ), and the diene’s double-bond has the attached carbons in a cis arraignment. Thus, as shown in Figure 3, the final product was predicted to form a cyclohexene ring attached to the maleic anhydride ring, with the two substituents on the diene on the same plane in relationship to each other, the ether ring carbons formerly attached to the double bond on the same plane as one another, but with the two substituent pairs trans of one another due to steric effects hindering their being equiplanar in relation to the cyclohexene ring segment.
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  • Fall '13
  • Dr.Chapman
  • Biotechnology, Carboxylic acid, final product, Organic reaction, Nuclear magnetic resonance, Proton NMR, acid anhydride

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