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DielsAlder-Report

DielsAlder-Report - Diels-Alder Itrtroduction The...

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Diels-Alder Itrtroduction: The Diels-Alder reaction is a stereospecific cycloaddition between a diene and a diemphile. This rcaction is alsopedcyclic, meaning tbat it's concerted and only involves a single cyclic intermediate in which bonds aIe simultaneously being formedand broken. ln order fo. such a cyclic intermediate to form, the dienemust be both conjugated and in the cis conformation. Dienedienophile pairs are €sp€cially effective reagents and therefore shift the reaction in favor ofthe product, when their electron distibutions differ as occurs when electon-withdrawing substitueots ar€ incorpomted in the dienophile' Although the Diels-Alder r€action is stercospecific, endo and exo diastereomers can form wten one or both ofthe reagents is a cyclic molecute. A bridge is formed in the adduct and in - . - - - . . : . r . _ _ ! : tlte endo product this bridge is on the same sideofthe molecule as the hydrrogen atoms at either ' sideofwhat was previously the catbon-carbon double bond ofthe dienophile' The exo product is then the reverse. in which these hydrogens areon the opposite sideofthe molecule as the bridge., .l --.l ,^'.-rI'! \{..t 1. ,-Y./, i In this lab, strictly the Q-c-pheltandrene isorlrcr is used so that strictly the endo adduct . \ will be synthesized.)The endo product is usually fg{ored in Diels-Alder rcactions because lhe
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