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Multiple Choice
Which aldol addition product is formed when two molecules of (acetaldehyde) undergo base-catalyzed aldol condensation?
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Identify the reactants and conditions: Two molecules of acetaldehyde (CH\_3CHO) undergo a base-catalyzed aldol reaction. The base deprotonates the alpha hydrogen of one acetaldehyde molecule to form an enolate ion.
Form the enolate ion: The alpha hydrogen adjacent to the carbonyl group in acetaldehyde is acidic. Under basic conditions, this hydrogen is removed, generating a resonance-stabilized enolate ion, which acts as a nucleophile.
Nucleophilic attack on the carbonyl carbon: The enolate ion attacks the electrophilic carbonyl carbon of a second acetaldehyde molecule, forming a new carbon-carbon bond and generating an alkoxide intermediate.
Protonation of the alkoxide intermediate: The alkoxide ion formed is protonated by water or the solvent, resulting in the aldol addition product, which is a β-hydroxy aldehyde. In this case, the product is 3-hydroxybutanal (CH\_3CH(OH)CH\_2CHO).
Recognize that this aldol addition product can further undergo dehydration under the reaction conditions to form an α,β-unsaturated aldehyde, but since the question asks for the aldol addition product, focus on the β-hydroxy aldehyde structure.