In the first step of the aldol condensation reaction, a base may remove an α-proton from the substrate to generate what intermediate?.

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04-11-2022
Chemistry

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In the first step of the aldol condensation reaction, a base may remove an α-proton from the substrate to generate what intermediate?.

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RadhaYadav216 RadhaYadav216 · Answer 1 · 2022-11-08T08:57:39-05:00

Step 1: The carbonyl group's oxygen undergoes protonation.

Step 2: The acidic hydrogen will be removed by the water molecule acting as a base, resulting in the creation of Enol.

Step 3 involves the enol attacking a second ketone molecule's protonated carbonyl group.

A carbonyl molecule and an enolate ion combine in the presence of an acid/base catalyst to produce a β-hydroxy aldehyde or β-hydroxy ketone, which is then dehydrated to produce a conjugated enone. It is a helpful process for creating carbon-carbon bonds.

The nucleophilic enolate ion attacks the aldehyde at the electrophilic carbonyl carbon. This assault produces an alkoxide intermediate and is a nucleophilic addition process. The water molecule is deprotonated by the alkoxide, resulting in hydroxide and β-hydroxy aldehyde.

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