DIELS-ALDER REACTION

DIELS-ALDER REACTION - DIELS-ALDER REACTION Overview: The...

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DIELS-ALDER REACTION Overview: The Diels-Alder reaction combines a diene (a molecule with two alternating double bonds) and a dienophile (an alkene) to make rings and bicyclic compounds. The three double bonds in the two starting materials are converted into two new single bonds and one new double bond. Since this reaction forms two new carbon-carbon bonds in a single step, it is a very useful and powerful reaction (one which earned Otto Diels and Kurt Alder a Nobel prize in chemistry for discovering it). Typically, the Diels-Alder reaction works best when either the diene is substituted with electron donating groups (like -OR, -NR 2 , etc) or when the dienophile is substituted with electron-withdrawing groups (like -NO 2 , -CN, -COR, etc). Conformational requirements of the diene One quirk of the Diels-Alder reaction is that the diene is required to be in the s-cis conformation in order for the Diels-Alder reaction to work. The s-cis conformation has both of the double bonds pointing on the same side of the carbon-carbon single bond
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DIELS-ALDER REACTION - DIELS-ALDER REACTION Overview: The...

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