Why is a ketone more acidic than an ester?
Yes, it is the other way around. Ketones (pKa ~ 20) are more acidic than esters (pKa ~ 25). Hence, the ester enolate anion resonance structure IV plays a smaller role and the enolate anion is less stabilized in the ester compared to the ketone. Consequently, the ester is less acidic than the ketone.Click to…
Yes, it is the other way around. Ketones (pKa ~ 20) are more acidic than esters (pKa ~ 25). Hence, the ester enolate anion resonance structure IV plays a smaller role and the enolate anion is less stabilized in the ester compared to the ketone. Consequently, the ester is less acidic than the ketone.Click to see full answer. Hereof, why is a ketone more reactive than an ester?so the ester is more reactive than the acid. Since the -OR group is a stronger electron donor (resonance) than the alkyl group of the ketone, the ester is less reactive than the ketone so we get : (b) The aldehyde, carboxylic acid and ester will be reduced to the same product, benzyl alcohol.Also Know, which is more acidic carboxylic acid or ester? For example, in nucleophilic substitution, then the ester is more reactive than the carboxylic acid. The reason is that esters have better leavings groups than the hydroxyl group of the carboxylic acid. ANd since it’s a carboxylic acid, there’s a high chance it’ll be a carboxylate (deprotonated) in its natural form. Simply so, why are aldehydes more acidic than ketones? Acidity of aldehydes and ketones and enolate formation. In most academic courses you’d learn that aldehydes are more acidic (lower pKa) than ketones due to the lower electron donating effect of the proton compared to the alkyl group of the ketone.Are esters more acidic than alcohols?Esters are more polar than ethers, but less so than alcohols. They participate in hydrogen bonds as hydrogen bond acceptors, but cannot act as hydrogen bond donors, unlike their parent alcohols and carboxylic acids.
