Which compound is formed as the major product when two molecules of (butanal) undergo aldol condensation in the presence of base?
A
(butanol)
B
(4-oxohexanal)
C
(butanoic acid)
D
(3-hydroxyhexanal)
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1
Identify the reactant: two molecules of butanal (CH\_3CH\_2CHO) are undergoing aldol condensation in the presence of a base.
Recall the mechanism of base-catalyzed aldol condensation: the base abstracts an alpha hydrogen from one aldehyde molecule to form an enolate ion.
The enolate ion then attacks the carbonyl carbon of a second butanal molecule, forming a new carbon-carbon bond and resulting in a β-hydroxy aldehyde intermediate.
Recognize that the initial product before dehydration is a β-hydroxy aldehyde, specifically 3-hydroxyhexanal, formed by the combination of the two butanal molecules.
Note that further dehydration of this β-hydroxy aldehyde under the reaction conditions can lead to an α,β-unsaturated aldehyde, but the major product immediately after aldol addition is the β-hydroxy aldehyde (3-hydroxyhexanal).