Aldol condensation outline.docx

Aldol condensation outline.docx - Aldol condensation...

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Aldol condensation: synthesis of Dibenzalacetone Condensation reactions: reactions that add together two or more molecules, often with the loss of water or an alcohol. General Aldol Condensation: 2 aldehydes react in the presence of base to form a β-hydroxyaldehyde (addition product) o then lose water to form an α,β-unsaturated aldehyde OR 2 ketones react in the presence of base to form a β-hydroxyketone (addition product) o then lose water to form an α,β-unsaturated ketone A carbon-carbon bond is formed between the alpha carbon of 1 molecule and the carbonyl cation on the other addition step. Loss of water typically facilitated by heat. EXCEPT when one of the starting carbonyls has conjugation. General reaction and mechanism: This is a reaction in which the carbonyl compound acts as a nucleophile as well as an electrophile. Reaction: The addition product (the β-hydroxyaldehyde) can also be called an aldol. It contains both an aldehyde group and an alcohol group. Base catalyzed reaction – so all intermediates must be negatively charged or neutral. Requirements in order for an aldol reaction to occur In order for a carbonyl to form an enolate: It needs to have at least 1 alpha H
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