Aldol_II - The Aldol Reaction Crossed/Directed Aldol...

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H O R 1 H O R 2 KOH, H 2 O 1 2 H O 1 = N u , 1 = E + R 1 OH R 1 H O 1 = N u , 2 = E + R 1 OH R 1 H O 2 = N u , 2 = E + R 2 OH R 2 H O 2 = N u , 1 = E + R 1 OH R 2 The Aldol Reaction: Crossed/Directed Aldol Reactions If two aldehydes, each possessing α -hydrogens, are exposed to aldol condensation conditions, four products will result. Let’s see how we can improve the selectivity of this process. Our ultimate goal is to condense two different carbonyl compounds and obtain a single “crossed”aldol product.
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The Aldol Reaction: Crossed/Directed Aldol Reactions H O R 1 H O KOH, H 2 O 1 2 H O 1 = N u , 1 = E + R 1 OH R 1 H O 1 = N u , 2 = E + R 1 OH NOTE: 2 has no α -hydrogens In this case, “aldehyde 2” has no α -hydrogens. Thus, we eliminate all products that derive from “aldehyde 2” serving as the nucleophilic partner. Only two possible products arise: the self-condensation of “aldehyde 1” and The crossed condensation of “aldehyde 1” with “aldehyde 2”. Still, we have two products and it would be desirable to have
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Aldol_II - The Aldol Reaction Crossed/Directed Aldol...

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