Statement TypeDirection (Q. Nos. 16-19) This section is based on State...
Reversibility of aldol into carbonyls establishes that carbanion nucleophile is formed in first fast reversible step.
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Statement TypeDirection (Q. Nos. 16-19) This section is based on State...
Statement I: In aldol condensation, enolates are nucleophilic and reversibly attack the carbonyl carbon of aldehyde or ketone in the aldol condensation.
The statement describes the mechanism of aldol condensation, which is a reaction between two carbonyl compounds (aldehyde or ketone) to form a β-hydroxy carbonyl compound. The enolate ion, formed by deprotonation of the α-hydrogen of a carbonyl compound, acts as a nucleophile and attacks the electrophilic carbonyl carbon of another carbonyl compound. This results in the formation of a new carbon-carbon bond and the elimination of a water molecule.
Statement II: An aldol on refluxing with dilute base gives back the carbonyl compound.
This statement suggests that the aldol condensation reaction is reversible. When an aldol product is refluxed with a dilute base, such as aqueous NaOH, the β-hydroxy carbonyl compound undergoes a base-catalyzed dehydration reaction to regenerate the starting carbonyl compound. This is achieved by the elimination of a water molecule from the β-hydroxy carbonyl compound.
Explanation:
Statement I and Statement II are both correct and Statement II provides the correct explanation for Statement I. Here's why:
- In aldol condensation, enolates act as nucleophiles and attack the carbonyl carbon of another carbonyl compound. This attack results in the formation of a new carbon-carbon bond and the formation of a β-hydroxy carbonyl compound. The enolate ion is a strong nucleophile due to the presence of a negative charge on the oxygen atom and the presence of a double bond (π bond) between the carbon and oxygen atoms.
- The reversibility of the aldol condensation reaction is demonstrated by Statement II. When the aldol product is refluxed with a dilute base, the β-hydroxy carbonyl compound undergoes a dehydration reaction. This reaction is base-catalyzed and involves the elimination of a water molecule from the β-hydroxy carbonyl compound. The resulting intermediate is an α,β-unsaturated carbonyl compound. Upon further heating or treatment with a stronger base, this intermediate can undergo additional reactions, such as conjugate addition or Michael addition.
In summary, aldol condensation involves the nucleophilic attack of enolates on carbonyl compounds, leading to the formation of β-hydroxy carbonyl compounds. The reaction is reversible, and the aldol product can be regenerated by refluxing with a dilute base and eliminating a water molecule.