I don't know if this question is kind of vague. But i was wondering like in the reaction of saponification of ester, where you have a base like OH- directly attacking the carbonyl carbon, can you also have a base like OH- attack the carbonyl carbon atom and then protonate the O- atom to create like a hydrate? Or does the base prefer attack hydrogen of alpha carbon of ketone and aldehyde? I am kind of confused about when a enol is create and when a hydrate is created since both of them can be formed by a base. So, hence I ask this question.
Ester hydrolysis and the soap-making process
In aqueous solution, esters are subject to hydrolysis to the corresponding carboxylic acid and alcohol components:
Hydrolysis is, the reverse of the esterification reaction. The addition of base accelerates ester hydrolysis because the nucleophile is a hydroxide ion, which is much more reactive than a water molecule.
The a-protons of carbonyls, are somewhat acidic, because the negative charge on the conjugate base is stabilized by resonance with the carbonyl oxygen. In the formation of an enol, a base abstracts an a-proton from a carbonyl compound, and that same proton (or a proton on a nearby acid group) is transferred to the carbonyl oxygen. The deprotonated form of an enol is an enolate.
However in this scenario I don't think an enolate will form in this case.
- enol formation is favored in acidic environments rather than basic
The preffered route would be the first one above.
To avoid a bit confusion:
To avoid generalisation, the R1 group given on the ester can be anything from -C(CH2)3, in this case 2 alpha carbons and no alph hydrogen. (No enol possible)
an alpha hydrogen may be there but reaction conditions won't favour enol formation.
Hope this clears doubts