The Reaction of Trans, Trans-2,4-Hexadiene-1-Ol with Maleic Anhydride

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Abstract: The aim was to react trans, trans-2,4-Hexadiene-1-ol with maleic anhydride. The reaction was a Diels-Alder reaction and it produced cis-1,3,3a,4,5,7a-Hexahydro-5-methyl-3-oxo-4-isobenzofuran-carboxylic acid. This reaction gave a percentage yield of 72%. The reaction product was purified and the melting point of both the crude and purified product was found. The purification step reduced the percentage yield to 47%. TLC was used to analyse how pure the product was and to see if any starting material remained. The TLC indicated there was no starting material present in the product. An IR spectrum was used to analyse the bonds present in the product. Bonds characteristic of the product were present which signals that the correct product was made. introduction: The reaction between trans, trans-2,4-Hexadiene-1-ol and maleic anhydride is a Diels Alder reaction. It is an example of [4+2] cycloaddition The Diels Alder reaction involves the redistribution of electrons and bonds. There are no reactive intermediates as all reaction steps occur at once; the electrons are cyclically redistributed. It is an example of a pericyclic process. Two double bonds disappear and reappear between two atoms that used to share a single bond. Two new single bonds form. This reaction proceeds via a transition state. Electron donating substituents attached to the diene, accelerate the reaction as do electron withdrawing groups on the dieneophile . The Alcohol acts as the diene and the anhydride as the dieneophile. The Diels–Alder reaction is a highly stereoselective reaction. In order for the reaction to occur the diene must be in the s-cis formation .The trans, trans-2,4-Hexadiene-1-ol can adopt the cis formation by rotating around a sigma bond while still maintaining Trans stereochemistry . The position of the diene to the dieneophile in the transition state determines the

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