Why are ketones acidic? - Chemistry Stack Exchange
Jul 3, 2016 · When a acid dissociates, it forms a hydrogen ion and the conjugate base of the acid. Remember, acid and base are only relative terms. The species which loses a proton in the reaction is acting as an acid and that which gains a proton is a base. In the example above, the ketone is acting as an acid because it donates a proton.
Cyclisation of acetone on reaction with conc. H2SO4
Dec 21, 2019 · Acid-catalyzed dehydration of 2 via the enol 3 leads to mesityl oxide 4. The loss of water from 3 may be stepwise but, to save space, I have presented the loss of water in a single operation. The third unit of acetone is incorporated via …
Is an ester or a ketone more acidic? - Chemistry Stack Exchange
Oct 31, 2014 · Yes, it is the other way around. Ketones (pKa ~ 20) are more acidic than esters (pKa ~ 25). The figure below shows the resonance structures for the enolate anion, a conjugate base of a ketone or ester. Resonance structures II and IV stabilize the enolate anion in the ketone and ester respectively.
What is the mechanism for oxidation of ketones by the Popoff's …
Mar 18, 2013 · If the ketone is unsymmetrical, there is no guarantee that is will cleave predictably. For example, 2-butanone could cleave into propanoic acid and carbon dioxide or two equivalents of acetic acid. $$\ce{CH3CH2COCH3 ->[\ce{HNO3}] n(CH3CH2COOH + CO2) + (1-n)(2CH3COOH)}$$
organic-chemistry spectroscopy ir-spectroscopy - Chemistry Stack …
Dec 29, 2015 · Acid: $1710$, Ketone: $1715$, Ester: $1730$ (all $\mathrm{cm^{-1}}$) This would seem to suggest that the acid decreases the carbonyl bond strength and the ester weakens it. This must be as a result of the fact that in the ester inductive withdrawal is more effective than resonance and the converse is true in the acid.
Why can't the reaction of grignard reagent with carboxylic acid …
Feb 16, 2017 · It acts as a base in the presence of a proton source (eg: alcohols, amine, water, etc). But when reacting with a ketone or an aldehyde, it acts as a nucleophile and uses a specific reaction mechanism. Why isn't that same reaction mechanism not viable for reaction with carboxylic acid? Why is this reaction mechanism wrong?
Rationalising the order of reactivity of carbonyl compounds …
Jul 25, 2014 · The HOMO of water is one of the lone pairs at oxygen, at $-6.35~\mathrm{eV}$. Correlating the LUMO energies from the table, the expected order of reactivity is $$\ce{acid~chloride > anhydride\approx aldehyde > ketone > acid\approx ester > amide}$$
Why are the boiling points of aldehydes less than those of ketones?
Nov 18, 2013 · $\begingroup$ Have a look at the comments to the answer of Rauru Ferro. He has posted a link that shows data which imply that it is not generally true that ketones have a higher boiling point than aldehydes - in fact they seem to be very similar and which one is higher changes within the homologous series.
Reaction/complexation of aluminium chloride and acetic acid
Jan 1, 2021 · In the end formation of a ketone-aluminium chloride complex is not a big problem because when chemist who was running the reaction decides to isolate the product, the ketone can be liberated by hydrolysis of that complex using aqueous acid (note that water is unwanted in Friedel-Crafts reaction).
Why is the pKa of a ketone higher than of water?
Dec 18, 2016 · The pKa of water is 16, while the pKa of a ketone, HC3(CO)CH3, is closer to 20. The lower the pKa the stronger the acid. When a ketone loses a hydrogen, the NBE are resonance stabilized into the carbonyl group, lowering their energy, increasing the acidity. When a proton is removed from water, the NBE have no resonance structures.