Diels-Alder-f - D E PA RT M E N T O F C H E M I S T RY CHEM...

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DEPARTMENT OF CHEMISTRY CHEM 286L – Organic Chemistry Laboratory II Diels-Alder Condensation Reaction Introduction Otto Diels and his pupil Kurt Alder received the Nobel Prize in 1950 for their discovery and work on the reaction that bears their names. Its great usefulness lies in its high yield and high stereospecificity. A cycloaddition reaction, it involves the 1,4-addition of a conjugated diene in the s -cis conformation to an alkene in which two new σ bonds are formed from two π bonds. Chemical reaction This reaction is non polar in nature in that no charged intermediates are formed. Neither is it a radical reaction, since no unpaired electrons are involved. It is known as a concerted reaction, one in which several bonds in the transition state are simultaneously made and broken. When a cyclic diene and a cyclic dienophile react with each other as in a Diels-Alder reaction, more than one stereoisomer may be formed. The isomer that predominates is the one that involves maximum overlap of π electrons in the transition state. The transition state for the formation of the endo isomer in this reaction involves two overlapping structures with the diene directly
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Diels-Alder-f - D E PA RT M E N T O F C H E M I S T RY CHEM...

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