Can Aldehydes Form Enolates?
The Reaction Involves an Aldehyde Enolate Reacting with Another Molecule of the Aldehyde. Remember Enolates Are Good Nucleophiles and Carbonyl C Are Good...
The reaction involves an aldehyde enolate reacting with another molecule of the aldehyde. Remember enolates are good nucleophiles and carbonyl C are good electrophiles. Since the pKa of an aldehyde is close to that of NaOH, both enolate and aldehyde are present simultaneously.
What compounds can form Enolates?
Some bases that have been used for enolate anion formation are: NaH (sodium hydride, pKa > 45), NaNH2 (sodium amide, pKa = 34), and LiN[CH(CH3)2]2 (lithium diisopropylamide, LDA, pKa 36). Ether solvents like tetrahydrofuran (THF) are commonly used for enolate anion formation.
What Cannot form an enolate?
q Since carbonyl compounds which do not have alpha hydrogens can not form an enolate, they cannot undergo the aldol reaction. Therefore the simplest aldehyde, methanal (formaldehyde) cannot undergo the aldol reaction.
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