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  2. Ester hydrolysis - Wikipedia

    en.wikipedia.org/wiki/Ester_hydrolysis

    Alkaline hydrolysis of esters is also known as saponification. A base such as sodium hydroxide is required in stochiometric amounts. Unlike acid-catalyzed ester hydrolysis, it is not an equilibrium reaction and proceeds to completion. Hydroxide ion attacks the carbonyl carbon to give a tetrahedral intermediate, which then expels an alkoxide ion.

  3. Ether cleavage - Wikipedia

    en.wikipedia.org/wiki/Ether_cleavage

    In organic chemistry, ether cleavage is an acid catalyzed nucleophilic substitution reaction. Depending on the specific ether, cleavage can follow either S N 1 or S N 2 mechanisms. Distinguishing between both mechanisms requires consideration of inductive and mesomeric effects that could stabilize or destabilize a potential carbocation in the S ...

  4. Taft equation - Wikipedia

    en.wikipedia.org/wiki/Taft_equation

    The hydrolysis of esters can occur through either acid and base catalyzed mechanisms, both of which proceed through a tetrahedral intermediate. In the base catalyzed mechanism the reactant goes from a neutral species to negatively charged intermediate in the rate determining (slow) step , while in the acid catalyzed mechanism a positively ...

  5. Hydrolysis - Wikipedia

    en.wikipedia.org/wiki/Hydrolysis

    Acid–base-catalysed hydrolyses are very common; one example is the hydrolysis of amides or esters. Their hydrolysis occurs when the nucleophile (a nucleus-seeking agent, e.g., water or hydroxyl ion) attacks the carbon of the carbonyl group of the ester or amide. In an aqueous base, hydroxyl ions are better nucleophiles than polar molecules ...

  6. Boronic acid - Wikipedia

    en.wikipedia.org/wiki/Boronic_acid

    Hydrolysis of boronic esters back to the boronic acid and the alcohol can be accomplished in certain systems with thionyl chloride and pyridine. [25] Aryl boronic acids or esters may be hydrolyzed to the corresponding phenols by reaction with hydroxylamine at room temperature. [26]

  7. Transesterification - Wikipedia

    en.wikipedia.org/wiki/Transesterification

    Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. [1] Strong acids catalyze the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile.

  8. Hammett equation - Wikipedia

    en.wikipedia.org/wiki/Hammett_equation

    The archetypal reaction is the alkaline hydrolysis of ethyl benzoate (R=R'=H) in a water/ethanol mixture at 30 °C. Measurement of the reaction rate k 0 combined with that of many substituted ethyl benzoates ultimately result in a reaction constant of +2.498. [3] [needs update] [non-primary source needed] Scheme 2. Hydrolysis of benzoic acid esters

  9. Ortho ester - Wikipedia

    en.wikipedia.org/wiki/Ortho_ester

    Ortho esters are readily hydrolyzed in mild aqueous acid to form esters: . RC(OR ′) 3 + H 2 O → RCO 2 R ′ + 2 R ′ OH. For example, trimethyl orthoformate CH(OCH 3) 3 may be hydrolyzed (under acidic conditions) to methyl formate and methanol; [5] and may be further hydrolyzed (under alkaline conditions) to salts of formic acid and methanol.